Home Vacation Rentals By Owner In Chicago, IL

Showing 2460 Of 2640 Vacation Rentals
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$156.0

/ Nightly
Apartment

Exceptional River North 1BR w/ Pool, nr Riverwalk & L, by Blueground

Chicago, Illinois, United States

Feel at home wherever you choose to live with Blueground. You’ll love this lovely River North furnished one bedroom apartment with its modern decor, fully equipped kitchen, and exquisite living room with great views. Ideally located, you’re close to all the best that Chicago has to offer! (ID #CHI1030)brbrDesigned with you in mindbrbrThoughtfully designed with bespoke finishes, modern furnishings, and a fully equipped kitchen, you’ll enjoy that “I’m home” feeling with this Blueground apartment. Whether you’re lounging in your stylish living room streaming the latest and greatest entertainment on the smart TV or premium wireless speaker, or getting some well-earned rest on the superior quality mattress with fully stocked linens, you’ll fall in love with everything this River North apartment has to offer. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr Queen Bed, 63in/160cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - BBQ Areabr - Dryerbr - Elevatorbr - Swimming poolbr - Washing machinebr - LoungebrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished apartment is located in River North, Chicago’s most trendy neighborhood. The bridges combined with the river walk offer incredible views. Nearby on Michigan Avenue is the city’s premier shopping area. One of the neighborhood’s biggest assets is the walk-to-work appeal. Young professionals, who live and work in the area, can quickly get to the office in the morning and just as easily enjoy an after-work drink, as the area is considered a premier entertainment center. Don’t miss a stroll on Kinzie and Hubbard streets. Merchandise Mart, the iconic building with showrooms, shops, and office space, is only a 5 minute walk. The Loop is just across the bridge and is about 5 minute walk.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - Building requires 48h to confirm the booking and validate the required documentsbr - This apartment is accessible for people with physical disabilities
Bed 1

Bed

Bath 1

Bath

Sleep 2

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Exceptional(25)

$214.37

/ Nightly
Condo

LOCATION!! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities!

Chicago, Illinois, United States

Luxury condo in a FANTASTIC location! Remodeled upscale condo located on the brink of River North/Gold Coast/Streeterville! Perfect for an extended vacation, short-term, long-term, or corporate rental. Amazing unobstructed views from 51st Floor! Outstanding views of the City & Lake Michigan. Full-Amenity building with 24hr doorman, newly remodeled sundeck with grills & firepits, updated outdoor pool and deck, PreCor fitness center & business center. Cable, WiFi & internet included. Steps to many Chicago attractions including the beach, shopping on the Magnificent Mile, restaurants & nightlife!brAlso see our other condos #971644 & #2844690 for additional availability.brbrThis fully furnished, professionally decorated condo with 2 bedrooms - each with walk-in closet, 2 spa-like baths, open kitchen with higher end stainless steel appliances, custom cabinets, beautiful granite counter-tops, living area, dining area, and entertainment area with wine console. Full size front load washer and dryer in unit. Fireplace, large screen HDTVs in both bedrooms and living area. Nothing else to bring except for your suitcases!brbrLocated on the 51st floor, this corner condo gives you amazing views of Chicago, Michigan Avenue, Lake Michigan and landmark buildings. 24/7 doorman for great security. Parking also available at an additional cost. A Chicago ordinance requires a minimum of one-month rental. Our HOA requires a lease for all rentals.br
Bed 2

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Bath 2

Bath

Sleep 5

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Very Good(1)

$448.47

/ Nightly
Apartment

Retreat Near Andersonville 3BR Newly Remodeled

Chicago, Illinois, United States

Requires walking up 2 flights of stairs.brbrEnjoy your stay in this beautifully updated 3-bedroom, 2-bath apartment near the heart of Andersonville. Perfect for families or groups, the space features modern finishes, a spacious living area, and a fully equipped kitchen. Located in a vibrant, walkable neighborhood filled with top-rated restaurants, cafes, and local shops. Easy access to public transit makes exploring Chicago a breeze. Comfort, style, and location come together for a memorable stay.brbrThe space:brThis spacious 3-bedroom, 2-bath apartment near Andersonville is designed for comfort, style, and convenience. The open living area is bright and welcoming, with modern furnishings and plenty of space to relax or gather. The fully equipped kitchen features updated appliances, ample counter space, and everything needed for home-cooked meals. Each bedroom offers a comfortable bed, soft linens, and generous storage, providing a peaceful retreat for every guest. The two full bathrooms are clean, modern, and well stocked with fresh towels and essentials, making this home ideal for families, groups, or longer stays.brbrGuest access:brYou’ll have access the the entire unit during your stay as well as the laundry room (paid laundry) conveniently located in the building.brbrOther things to note:brWe do not have designated parking but free street parking is available in the neighborhood. That said, please take care to read any signs indicating no parking or tow zones to avoid any issues. Parking availability can fluctuate depending on the time of day, and if you arrive later in the evening, there’s a chance that spots might be harder to find.brbrIn case you run into this situation, we suggest using the SpotHero app or ParkWhiz to easily locate an affordable and convenience parking spot nearby.brbr**HOUSE RULES**brbrWe want you to have a comfortable and enjoyable stay! To help keep the space safe, clean, and pleasant for everyone, please review and follow the house rules below. Failure to comply may result in cancellation or additional charges.brbrShoes off, please. Kindly remove shoes upon entering the unit.brbrNo smoking anywhere inside the unit or on the property. Smoking will result in immediate cancellation and a $200 damage fee.brbrNo drugs, including marijuana.brbrNo illegal activities anywhere on the property.brbrNo parties or events.brbrNo outside visitors.brbrNo overnight guests without prior approval from the host.brbrFood storage: Please store all food in designated areas and do not leave food out to help prevent pests.brbrKitchen use: Feel free to use the kitchen, but please clean up after yourself. Wash dishes, wipe counters, stove, and microwave. No dirty dishes left in the sink overnight.brbrDamages: If anything is broken or damaged, please let us know right away so we can arrange repair or replacement.brbrCheckout cleaning:brPlease wash dishes, return moved furniture to its original place, and take out the trash before checkout.brThe standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty (dirty dishes, trash left throughout the unit, etc.), an additional cleaning fee of up to $100 may apply.brbrTowels & linens: Provided for your entire stay. If you need extras, please let us know in advance. A $50 fee applies to cover the cleaner’s trip. Paid laundry facilities are available in the building.brbrLost keys: A $300 fee applies for lock and key replacement. Please note that lost keys cannot be replaced immediately, and you may temporarily lose access to the unit and building amenities.brbrQuiet hours: Please observe quiet hours from 10:00 PM – 8:00 AM.brbrLate checkout: Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.brbrThank you for your understanding and cooperation -we truly appreciate it and look forward to hosting you!
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(4)

$561.49

/ Nightly
Condo

Downtown 2bd #6 +Gym near Park, Lake, Museums

Chicago, Illinois, United States

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park!brbrMost homes don’t provide professional service along with “local vibes.” Guests love staying with us because:brCentral Location near public transit (no car needed!)brFAST WIFIbrOn-floor free laundrybrLake & Park are 1 1/2 blocks awaybrComfy Queen bedsbrGymbr3 blocks from Red `L` subwaybrClose to Grant Park, The Bean, Soldier Field, MuseumsbrbrIf you`re interested in booking, see our FAQs below.brbrDrop your bags in your private space, complete with cozy beds, sky-high ceilings, and expansive windows allowing sunlight to pour in.brbrMake your way to the fitness center for a quick workout and then grab a breath of fresh air at Grant Park.brbrTime to hit the pavement. Saunter the art-filled halls at the Art Institute of Chicago. Wander past the 19th-century mansions on Prairie Avenue. Then fill your belly at The Dearborn (we recommend the mouth-watering fish and chips). Trade your sneakers for your go-to night-out pair. Let your ears guide you to the bustling bars. Try a new cocktail. Or order a pint and join the locals as they cheer on the Cubs.brbrWorking, relaxing, living. Our spaces have all the other essentials you need for your stay. brbr- Front desk check-in br- Super-fast WiFibr- Fresh towels and bathroom essentials br- Pre-cleaning before your arrivalbr- Fitness centerbr- On-floor free laundrybr- Fully equipped kitchenbrbrPlease note that the building is shared with a college so you may see some college kids, but our floor secured and leased by us.brbrOnce you get inside the building, you walk to the secure elevators to go up to your floor.brbrOnce to the floor, you walk to your apartment. Once in the apartment, you will find a modern space with two bedrooms, one bathroom, a modern kitchen, and a living room equipped with Smart TV.brbrYou have private, full access to the unit, the shared gym, and the basketball court.brbrWe`re here to help, but give you space to enjoy!brbrGuests are not allowed to check-in or be sent check-in information without providing: 1) Names 2) Ages 3) Emails and 4) Phone because they need to be sent to the front desk security. brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 25 to bookbrbr - brTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbrThe base price for this home is for 3 guests only. There will be an extra guest fee of $15 per guest per night if your group exceeds to 3 people.brbrNO PETS allowed. We`re sorry.brbrNo Animal PolicybrPlease note that the building has strict no-animal policies in place, which include service animals and emotional support animals. These restrictions are managed by building management and apply to all residents and guests for health and safety reasons.brbrThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbr : brA: Very much so. 24 hours a day.brbr : , , brA: Nope! we provide all these things. We also provide you and your guests with a starter pack of toilet papersbrbr : brA: Check in is 4pm and check out is 10am. Early check ins can be difficult if there are guests who checked out same day. We ask for an early check-in, or a late-check out fee, if you request either.brbr : brA: Yes, it is shared so please be respectful of other tenants and guests using the space.brbr : - / brA: If you do not have flights that coincide with our check-in and checkout times, you may store your bags with Radical Storage near our property. It allows you to store your bags for your optimal time :)brbr : brA: Yes. And we wouldn`t trust any listing with which this isn`t the case.brbr : brA: We don’t recommend driving because we are so centrally located. You may find a lot or garage nearby for $18-30 / night. There are multiple garages or valet services within 2 blocks.brbr : brA: Yes, and we take pride in providing a clean home for guests.brbr : ` brA: We honestly have no idea. With fees included, it only shows the guest how much they pay. This figure should be present after you enter your dates. Note that, pricing varies on a daily basis, and it actually uses some crazy algorithm to adjust it automatically, so I don`t actually control this.brbr : brA: Very. Some guests say they`re the best they`ve ever slept on!brbrNo Agency Relationship. Nothing herein contained shall be deemed to authorize or empower either party to act as agent for the other party to this Agreement, or to conduct business in the name, or for the account, of the other party to this Agreement.brbr brAs part of our vetting process, we may ask guests to confirm a few details — such as their names, ages, where they’re traveling from, or their travel plans — before accepting a booking. In some cases, we may also request a valid government-issued ID for verification purposes. This helps us ensure that all stays are safe, transparent, and in line with our house policies.brbrUnresponsive GuestbrIn some cases, if a guest does not respond within a reasonable period, we reserve the right to cancel the reservation. brFor same-day bookings, this timeframe is up to 2 hours or less. For all other bookings, this timeframe is up to 8 hours. This ensures that we can provide the best experience and availability for all our guests.brbrOnline Check-In & Rental Agreement RequiredbrBefore receiving check-in instructions, all primary guests must complete our online check-in form and review/sign our rental agreement. This helps verify guest details and ensures a smooth, secure arrival.brbrEXTRA GUEST CHARGEbrThe base price covers 3 guests. For more than 3 guests, there is an extra guest fee of $15 per guest for the full number of nights.brExample: 1 extra guest for a 5-night stay = $15 × 5 nights = $75.brbrKeys & AirTags:brFor transparency, some building keys or fobs may have an AirTag attached for loss prevention. The AirTag is only used to locate the key if it is lost and is never used to track guests or their movements. Guests are not required to carry the key at all times, but we recommend keeping the AirTag attached to help avoid replacement charges if the key is misplaced.brbrRefundable Security Deposit: A $300 refundable security deposit is required and will be `held` or `authorized` (not `charged`) by Chicago Hospitality Club on your card. Any property damage or extra charges may be deducted from the deposit. VRBO collects platform payments/charges separately, while Chicago Hospitality Club handles the deposit, so seeing both on your statement is normal. The deposit is automatically released 3-7 days after checkout.brbrSecurity Deposit (Families with Young Children)brA security deposit may be required for groups traveling with two or more children under 14 years old, as a precaution against accidental damage. The deposit is fully refundable, provided there is no damage to the property after a standard post-checkout inspection.brbrRefund Processing PolicybrIn the event of a guest-initiated cancellation, any bank fees or payment processing charges incurred will be the responsibility of the guest and will be deducted from the refund amount.brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 25 to bookbrbrLast-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbr -Up to the cost of any impacted nights subsequent to originally scheduled check-outbr / - $500.00 minimum charge and eviction from Rental Unitbr - Up to $125.00 per hour of additional cleaning neededbr - Varies depending on cost of itembrbr : potential warning issued or, if necessary, eviction with no refund and a charge of up to $1,000.00br - Up to $2,000.00br - $75 minimum charge for handling and shipping.brIf keys are left inside the home, and we come to give you re-entry it is $50.br - $50.00 minimum chargebr - $150.00 minimum chargebrNo Unauthorized Late Check Out without notice from Host.br-Early check-ins/Late check-outs can sometimes be accommodated by our cleaning service for $50 per hour fee.brbrThere is a NOISE MONITORING system within the home to track decibel noise level.
Bed 2

Bed

Bath 1

Bath

Sleep 5

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Exceptional(70)

$418.05

/ Nightly
Condo

STYLISH-LOCAL-COMFY-SAFE 4 night min.

Chicago, Illinois, United States

brLocated in Chicago’s Andersonville & Edgewater area. brbrDown the street from Loyola's campus and near great restaurants like Lonesome Rose, Lady Gregory, Big Jones, Anti Prima... the list goes on and on. Walking distance to Whole Foods, Jewel, and Devon Market.brbrShopping and lakefront 5 -10 min plenty of parking if you're renting a car or driving. Although between Uber & Lyft you really don't need a car or conveniently located for a short ride to all the destinations & hot spots and it's a short walk to the red line train. brbrThe three bedroom apartment is fully furnished, bright sunny, amazing layout and well appointed. Anything you could possibly need when traveling is here and in unit. brbrbrThe 3 bedrooms have Tempur-pedic mattresses and for new clean pillows per bed. 2 firm pillows and 2 soft per bed.brbrThe living room has a 85 3D smart TV with netflix with and all the premium cable channels, so you can keep up with the latest episodes and rent any current release...brIt includes a fully equipped kitchen. brbrGuest AccessbrYou will have high speed internet -full use if the entire unit and backyard. brbrInteraction with GuestsbrI will be glad to help in whatever way I can provide tips on local restaurants and other attractions.brbrThe Neighborhood is safe and quiet. It serves as an excellent balance between downtown shopping and all the amazing small Chicago neighborhoods.brbrThe space would also work well as a longer term, corporate rental.brbrHouse Rules- brWe look forward to ensuring a great stay for you.brbrWe ask that you be honest with how many guests will be staying in the unit- MAX .brWe do confirm amount of people staying in unit.brbrNo need to make beds your final day we strip beds and do a deep clean and disinfect between each guest. The property is clean and immaculate.
Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps

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$2853.01

/ Nightly
Condo

Downtown 9bd - Sleep 18 - (4 units, same floor)

Chicago, Illinois, United States

Feel at Home, Unwind, and Enjoy the amenities you deserve!brbrGuests love staying with us because:br-4 separate units for privacy, yet gatheringbr-Central Location near public transitbr-FAST WIFIbr-On floor free Laundrybr-Lake & Park are 1 1/2 blocks awaybr-Comfy King+Queen Bedsbr-Communal area to seat 15-20 on floorbr-Gymbr-3 blocks from Red `L` subwaybr-Close to Grant Park, The Bean, Soldier Field, MuseumsbrbrIf you`re interested in booking, see our FAQs below.brbrThis is a combination listing: brR24000120168brR24000120167brR24000120165brR24000120166brbrDrop your bags in your private space, complete with cozy beds, sky-high ceilings, and expansive windows allowing sunlight to pour in.brbrMake your way to the fitness center for a quick workout and then grab a breath of fresh air at Grant Park.brbrTime to hit the pavement. Saunter the art-filled halls at the Art Institute of Chicago. Wander past the 19th-century mansions on Prairie Avenue. Then fill your belly at The Dearborn (we recommend the mouth-watering fish and chips). Trade your sneakers for your go-to night-out pair. Let your ears guide you to the bustling bars. Try a new cocktail. Or order a pint and join the locals as they cheer on the Cubs.brbrWorking, relaxing, living. Our spaces have all the other essentials you need for your stay. brbr- Front desk check-inbr- Super-fast WiFibr- Fresh towels and bathroom essentialsbr- Pre-cleaning before your arrivalbr- Fitness centerbr- On-floor free laundrybr- Fully equipped kitchenbrbrPlease note that the building is shared with a college so you may see some college kids, but our floor secured and leased by us.brbrOnce you get inside the building, you walk to the secure elevators to go up to your floor.brbrOnce to the floor, you walk to your apartment. Once in the apartment, you will find a modern space with two bedrooms, one bathroom, a modern kitchen, and a living room equipped with Smart TV.brbrGuests are not allowed to check-in or be sent check-in information without providing: 1) Names 2) Ages 3) Emails and 4) Phone because they need to be sent to the front desk security.brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 30 to bookbrbr Last-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbrThe base price for this home is for 10 guests only. There will be an extra guest fee of $15 per guest per night if your group exceeds to 10 people.brbrNO PETS allowed. We`re sorry.brbrNo Animal PolicybrPlease note that the building has strict no-animal policies in place, which include service animals and emotional support animals. These restrictions are managed by building management and apply to all residents and guests for health and safety reasons.brbrForgotten Personal Belongings: $75 minimum chargebrbrThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbrQ: Is the neighborhood safe brA: Very much so. 24 hours a day.brbrQ: Do I need to bring towels, a hair dryer, or linens brA: Nope! we provide all these things. We also provide you and your guests with a starter pack of toilet papersbrbrQ: When can I check in or check out brA: Check in is 4pm and check out is 10am. Early check ins can be difficult if there are guests who checked out same day. We ask for an early check-in, or a late-check out fee, if you request either.brbrQ: Is the Gym shared brA: Yes, it is shared so please be respectful of other tenants and guests using the space.brbrQ: Luggage Drop-Off / Storage brA: If you do not have flights that coincide with our check-in and checkout times, you may store your bags with Radical Storage near our property. It allows you to store your bags for your optimal time :)brbrQ: Can I come and go as I please brA: Yes. And we wouldn`t trust any listing with which this isn`t the case.brbrQ: What about parking brA: We don’t recommend driving because we are so centrally located. You may find a lot or garage nearby for $18-30 / night. There are multiple garages or valet services within 2 blocks.brbrQ: Is the place professionally cleaned between guests brA: Yes, and we take pride in providing a clean home for guests.brbrQ: What`s my total booking price brA: We honestly have no idea. With fees included, it only shows the guest how much they pay. This figure should be present after you enter your dates. Note that, pricing varies on a daily basis, and it actually uses some crazy algorithm to adjust it automatically, so I don`t actually control this.brbrQ: Are the beds comfortable brA: Very. Some guests say they`re the best they`ve ever slept on!brbrNo Agency Relationship. Nothing herein contained shall be deemed to authorize or empower either party to act as agent for the other party to this Agreement, or to conduct business in the name, or for the account, of the other party to this Agreement.brbrGuest VerificationbrAs part of our vetting process, we may ask guests to confirm a few details — such as their names, ages, where they’re traveling from, or their travel plans — before accepting a booking. In some cases, we may also request a valid government-issued ID for verification purposes. This helps us ensure that all stays are safe, transparent, and in line with our house policies.brbrUnresponsive GuestbrIn some cases, if a guest does not respond within a reasonable period, we reserve the right to cancel the reservation. brFor same-day bookings, this timeframe is up to 2 hours or less. For all other bookings, this timeframe is up to 8 hours. This ensures that we can provide the best experience and availability for all our guests.brbrOnline Check-In & Rental Agreement RequiredbrBefore receiving check-in instructions, all primary guests must complete our online check-in form and review/sign our rental agreement. This helps verify guest details and ensures a smooth, secure arrival.brbrEXTRA GUEST CHARGEbrThe base price covers 10 guests. For more than 10 guests, there is an extra guest fee of $15 per guest for the full number of nights.brExample: 1 extra guest for a 5-night stay = $15 × 5 nights = $75.brbrRefundable Security Deposit: A $300 refundable security deposit is required and will be `held` or `authorized` (not `charged`) by Chicago Hospitality Club on your card. Any property damage or extra charges may be deducted from the deposit. VRBO collects platform payments/charges separately, while Chicago Hospitality Club handles the deposit, so seeing both on your statement is normal. The deposit is automatically released 3-7 days after checkout.brbrKeys & AirTags:brFor transparency, some building keys or fobs may have an AirTag attached for loss prevention. The AirTag is only used to locate the key if it is lost and is never used to track guests or their movements. Guests are not required to carry the key at all times, but we recommend keeping the AirTag attached to help avoid replacement charges if the key is misplaced.brbrSecurity Deposit (Families with Young Children)brA security deposit may be required for groups traveling with two or more children under 14 years old, as a precaution against accidental damage. The deposit is fully refundable, provided there is no damage to the property after a standard post-checkout inspection.brbrRefund Processing PolicybrIn the event of a guest-initiated cancellation, any bank fees or payment processing charges incurred will be the responsibility of the guest and will be deducted from the refund amount.br❎No Local Guests (City or Suburbs)br Quiet hours: 10pm to 8ambr Minimum age of 25 to bookbrbr Last-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbrThe base price for this home is for 4 guests only. There will be an extra guest fee of $10 per guest per night if your group exceeds to 4 people.brbr (Under 20lbs, no shedding) - $150.br - (Over 20lbs) - $200 plus a $200 refundable security deposit and subject to host approval.brIf the pet sheds, we will require an additional $150 refundable Security deposit.br - $250.00 plus any damages or additional cleaning costs incurredbrbr -Up to the cost of any impacted nights subsequent to originally scheduled check-outbr / - $500.00 minimum charge and eviction from Rental Unitbr - Up to $125.00 per hour of additional cleaning neededbr - Varies depending on cost of itembrbr : potential warning issued or, if necessary, eviction with no refund and a charge of up to $1,000.00br - Up to $2,000.00br - $75 minimum charge for handling and shipping.brIf keys are left inside the home, and we come to give you re-entry it is $50.br - $50.00 minimum chargebr - $150.00 minimum chargebrNo Unauthorized Late Check Out without notice from Host.br-Early check-ins/Late check-outs can sometimes be accommodated by our cleaning service for $50 per hour fee.brbrThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbrAll guest names and ages must be registered before you are allowed to check in.brbrGuest VerificationbrAs part of our vetting process, we may ask guests to confirm a few details — such as their names, ages, where they’re traveling from, or their travel plans — before accepting a booking.
Bed 9

Bed

Bath 5

Bath

Sleep 16

Sleeps

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Exceptional(1)

$561.85

/ Nightly
Condo

Downtown 2bd #5 +Gym near Park, Lake, Museums

Chicago, Illinois, United States

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park!brbrMost homes don’t provide professional service along with “local vibes.” Guests love staying with us because:br-Central Location near public transit (no car needed!)br-FAST WIFIbr-On-floor free laundrybr-Lake & Park are 1 1/2 blocks awaybr-Comfy Queen bedsbr-Gymbr-3 blocks from Red `L` subwaybr-Close to Grant Park, The Bean, Soldier Field, MuseumsbrbrIf you`re interested in booking, see our FAQs belowbrbrDrop your bags in your private space, complete with cozy beds, sky-high ceilings, and expansive windows allowing sunlight to pour in.brbrMake your way to the fitness center for a quick workout and then grab a breath of fresh air at Grant Park.brbrTime to hit the pavement. Saunter the art-filled halls at the Art Institute of Chicago. Wander past the 19th-century mansions on Prairie Avenue. Then fill your belly at The Dearborn (we recommend the mouth-watering fish and chips). Trade your sneakers for your go-to night-out pair. Let your ears guide you to the bustling bars. Try a new cocktail. Or order a pint and join the locals as they cheer on the Cubs.brbrWorking, relaxing, living. Our spaces have all the other essentials you need for your stay. br- Front desk check-inbr- Super-fast WiFibr- Fresh towels and bathroom essentialsbr- Pre-cleaning before your arrivalbr- Fitness centerbr- On-floor free laundrybr- Fully equipped kitchenbrbrPlease note that the building is shared with a college so you may see some college kids, but our floor secured and leased by us.brbrOnce you get inside the building, you walk to the secure elevators to go up to your floor.brbrOnce to the floor, you walk to your apartment. Once in the apartment, you will find a modern space with two bedrooms, one bathroom, a modern kitchen, and a living room equipped with Smart TV.brbrYou have full access to the private apartment, shared fitness, shared free laundry on the floor and shared basketball courts.brbrWe’re here to help but give you space and privacy to enjoy!brbrGuests are not allowed to check-in or be sent check-in information without providing: 1) Names 2) Ages 3) Emails and 4) Phone because they need to be sent to the front desk security. brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 25 to bookbrbrLast-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbrThe base price for this home is for 3 guests only. There will be an extra guest fee of $15 per guest per night if your group exceeds to 3 people.brbrNO PETS allowed. We`re sorry.brbrNo Animal PolicybrPlease note that the building has strict no-animal policies in place, which include service animals and emotional support animals. These restrictions are managed by building management and apply to all residents and guests for health and safety reasons.brbrThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbrQ: Is the neighborhood safe brA: Very much so. 24 hours a day.brbrQ: Do I need to bring towels, a hair dryer, or linens brA: Nope! we provide all these things. We also provide you and your guests with a starter pack of toilet papersbrbrQ: When can I check in or check out brA: Check in is 4pm and check out is 10am. Early check ins can be difficult if there are guests who checked out same day. We ask for an early check-in, or a late-check out fee, if you request either.brbrQ: Is the Gym shared brA: Yes, it is shared so please be respectful of other tenants and guests using the space.brbrQ: Luggage Drop-Off / Storage brA: If you do not have flights that coincide with our check-in and checkout times, you may store your bags with Radical Storage near our property. It allows you to store your bags for your optimal time :)brbrQ: Can I come and go as I please brA: Yes. And we wouldn`t trust any listing with which this isn`t the case.brbrQ: What about parking brA: We don’t recommend driving because we are so centrally located. You may find a lot or garage nearby for $18-30 / night. There are multiple garages or valet services within 2 blocks.brbrQ: Is the place professionally cleaned between guests brA: Yes, and we take pride in providing a clean home for guests.brbrQ: What`s my total booking price brA: We honestly have no idea. With fees included, it only shows the guest how much they pay. This figure should be present after you enter your dates. Note that, pricing varies on a daily basis, and it actually uses some crazy algorithm to adjust it automatically, so I don`t actually control this.brbrQ: Are the beds comfortable brA: Very. Some guests say they`re the best they`ve ever slept on!brbrNo Agency Relationship. Nothing herein contained shall be deemed to authorize or empower either party to act as agent for the other party to this Agreement, or to conduct business in the name, or for the account, of the other party to this Agreement.brbrGuest VerificationbrAs part of our vetting process, we may ask guests to confirm a few details — such as their names, ages, where they’re traveling from, or their travel plans — before accepting a booking. In some cases, we may also request a valid government-issued ID for verification purposes. This helps us ensure that all stays are safe, transparent, and in line with our house policies.brbrUnresponsive GuestbrIn some cases, if a guest does not respond within a reasonable period, we reserve the right to cancel the reservation. brFor same-day bookings, this timeframe is up to 2 hours or less. For all other bookings, this timeframe is up to 8 hours. This ensures that we can provide the best experience and availability for all our guests.brbrOnline Check-In & Rental Agreement RequiredbrBefore receiving check-in instructions, all primary guests must complete our online check-in form and review/sign our rental agreement. This helps verify guest details and ensures a smooth, secure arrival.brbrEXTRA GUEST CHARGEbrThe base price covers 3 guests. For more than 3 guests, there is an extra guest fee of $15 per guest for the full number of nights.brExample: 1 extra guest for a 5-night stay = $15 × 5 nights = $75.brbrKeys & AirTags:brFor transparency, some building keys or fobs may have an AirTag attached for loss prevention. The AirTag is only used to locate the key if it is lost and is never used to track guests or their movements. Guests are not required to carry the key at all times, but we recommend keeping the AirTag attached to help avoid replacement charges if the key is misplaced.brbrRefundable Security Deposit: A $300 refundable security deposit is required and will be `held` or `authorized` (not `charged`) by Chicago Hospitality Club on your card. Any property damage or extra charges may be deducted from the deposit. VRBO collects platform payments/charges separately, while Chicago Hospitality Club handles the deposit, so seeing both on your statement is normal. The deposit is automatically released 3-7 days after checkout.brbrSecurity Deposit (Families with Young Children)brA security deposit may be required for groups traveling with two or more children under 14 years old, as a precaution against accidental damage. The deposit is fully refundable, provided there is no damage to the property after a standard post-checkout inspection.brbrRefund Processing PolicybrIn the event of a guest-initiated cancellation, any bank fees or payment processing charges incurred will be the responsibility of the guest and will be deducted from the refund amount.brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 25 to bookbrbrLast-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbr -Up to the cost of any impacted nights subsequent to originally scheduled check-outbr / - $500.00 minimum charge and eviction from Rental Unitbr - Up to $125.00 per hour of additional cleaning neededbr - Varies depending on cost of itembrbr : potential warning issued or, if necessary, eviction with no refund and a charge of up to $1,000.00br - Up to $2,000.00br - $75 minimum charge for handling and shipping.brIf keys are left inside the home, and we come to give you re-entry it is $50.br - $50.00 minimum chargebr - $150.00 minimum chargebrNo Unauthorized Late Check Out without notice from Host.br-Early check-ins/Late check-outs can sometimes be accommodated by our cleaning service for $50 per hour fee.brbrThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbrAll guest names and ages must be registered before you are allowed to check in.brbrGuest Verification
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$195.0

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Apartment

Bucktown Loft - top floor, near Bloomingdale Trail

Chicago, Illinois, United States

Unique Bucktown loft studio on the top floor of a restored vintage Chicago building, central to Bucktown & Wicker Park. This 1895 building and loft has been restored and renovated with a brand new kitchen and bath with walk-in shower, central heat & AC. The unit is incredibly bright with windows on each and 5 skylights throughout.brbrBasic housekeeping included in stays over 45 days (every 3-4 weeks; not including laundry).brbrThe space is a large studio (about 800 sq ft) - with no walls between rooms/spaces (except the bathroom). The loft is on the 4th floor of a walk-up building (no elevator).brbrThe space is has a full kitchen, walk-in shower with glass enclosure, and in-unit washer dryer. The California King bed is on one side of the loft, with the living and dining area in the middle, and kitchen and bath on the other end. The private porch off the entrance has tree-top views of downtown Chicago.brbrGuests will have access to the full unit and private rear deck off the entry. The patio on the ground level is shared by all tenants in the building (there are 5 total units in the building, with this being the entirety of the top floor).brbrGuests will have access to the full unit and private rear deck off the entry. The patio on the ground level is shared by all tenants in the building (there are 5 total units in the building, with this being the entirety of the top floor).brbrNote: we may periodically access locked storage closets in the unit for maintenance purposes during your stay. We will always provide at least 24 hour notice, unless there is a maintenance emergency.
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$406.44

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Apartment

Minty Fresh • Vintage Lincoln Park Flat

Chicago, Illinois, United States

Summary:brbrEnjoy a stylish experience at this centrally-located designer flat. The location literally can't be beat, near Wrigley Field, the bustling Southport shopping corridor, DePaul University, and both the red line and brown line 'L' train stations. It's also close to all of the 'Boystown' nightlife.brbrbrbrThe Space:brbrI've used my years of experience a designer to set up this unique flat so that it includes all the comforts of home while embracing the quirky charm that only a vintage building can offer. brbrbrbrI believe in high standards of personal comfort, so you'll only find high thread count cotton sheets on the bed, comfortable pillows, a great mattress, and thick towels. The bath products are from Public Goods and seem to be universally liked. We also supply a good amount of coffee and some other little amenities to really make you feel looked after.brbrbrbrA friendly but important note about my flat:brbrbrbr1) This is on the third floor of a walk-up building, so you'll need to climb stairs to access.brbr2) If you're sensitive to noise, please also note that you may hear some occasional noise from my neighbors or from the nearby 'L' train. I've left a white noise machine and earplugs in the unit for sensitive sleepers.brbr3) This unit is located in a vintage building that's been updated but is still over 100 years old, so it comes along with little quirks that new buildings don't.brbrbrbrLOCATIONbrbrbrbrAlthough shops and restaurants are only a short walk away, the area feels peaceful and secluded. Because of my flat's central location, I strongly recommend leaving your car at home. Any point of interest in Chicago can easily be reached by walking, public transit, or Uber. brbrbrbrEXCLUSIVE PERKSbrbrbrbrDuring your stay as my guest, you receive a free membership to The Metropolitan, a members-only club and co-working space located on the 66th and 67th floors of the Willis Tower (for reservations 14 days only).brbrbrbrIncluded with your membership:brbr✔ Upscale co-working space, dining, and barsbrbr✔ Stunning views of Chicago and Lake Michiganbrbr✔ Discounted express tickets to the Willis Tower SkydeckbrbrbrbrMessage me for more details!brbrbrbrPARKING brbrbrbrParking isn't included and the streets around us are all either permitted (local residents only) or metered, so make sure not to use those spots. When parking, be sure to check all signs nearby because it's easy to get a ticket when parking rules are broken. For the easiest parking, we highly recommend using a service called SpotHero to reserve a spot nearby before you arrive.brbrbrbrGuest Access:brbrThe entire flat is yours. If you smoke, I ask that you go off of the property.brbrbrbrOther Things to Note:brbrFREQUENTLY ASKED QUESTIONSbrbrbrbrQ: “How do I get to ‘x’ from the apartment /How far is the apartment from ‘x’ ”brbrA: Excellent public transit directions from my flat to any point in the city are available via web search. My place is a short walk from the Wellington Brown Line “L” train station. Search for “Wellington Brown Line stop Chicago” in Maps, click the “Directions” button, then enter your point of interest.brbrbrbrQ: When is check-in/check-out brbrA: Check-in: Your reservation and access to the apartment both begin at 4 p.m. on your check-in date.brbrCheck-out: Your reservation and access to the apartment both end at 11 a.m. on your check-out date.brbrbrbrQ: “Is there parking nearby ”brbrA: Parking isn't included and the streets in the area are all either permitted (local residents only) or metered, so make sure not to use those spots. When parking, be sure to check all signs nearby because it's easy to get a ticket when parking rules are broken. For the easiest parking, I highly recommend using a service called SpotHero to reserve a spot nearby before you arrive.brbrbrbrQ: Can I smoke in the apartment brbrA. Sorry, no. If you smoke, I ask that you go off of the property (not outside of the back door). I will need to charge a $100 cleaning fee if there's any smoke smell inside of the apartment.brbrbrbrQ: “Does the unit have air conditioning/heating ”brbrA: Radiant heat is supplied to the unit by the building and is turned off and on by the building engineers. Window air conditioners will be installed starting mid-May.brbrbrbrInteraction with Guests:brbrI'm typically not available in person but my friends at Trove are available 24/7 to answer any questions that might pop up during your stay.
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$380.31

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Apartment

The Drapes of Wrath • Vintage Flat in Ravenswood

Chicago, Illinois, United States

Summary:brbrI’m an interior designer and longtime Superhost who believes you deserve better than scratchy sheets and a suspicious futon. Everything here was chosen with intention—and a sense of humor. From the agressive use of one pattern on everything to the WW2 era psychology test above the bed, this space is a little odd, very clean, and designed to feel like someone with great taste lives here. (Because, well, sometimes they do.)brbrbrbrThe Space:brbr10 takeaways for people who don’t have the patience to read my ramblingsbrbr(but still deserve a very nice place to stay)brbrbrbr• Sleeps 2 (King bed)brbr • Full kitchen + fast Wi-Fibrbr • Shower with (occasionally moody but mostly good) water pressurebrbr • Professionally cleaned by people who care deeply and would benefit from other hobbiesbrbr • AWESOME street, 10-minute stroll to the Brown Linebrbr • Ground floor unit in a vintage building (quirks included, free of charge)brbr • Hosted by a creative human, managed by professionals who actually pick up the phonebrbr • Thoughtful touches, compelling artbrbr • 24/7 phone support after bookingbrbr •The towels are nice and the bath products aren’t from a gas station. You’ll be finebrbrbrbrYou’re getting the best of both worlds here: I get to be your friendly, creative host—sharing local tips and a well-loved space—without also being the person scrubbing behind the toilet. (You're welcome.) That’s because I’ve partnered with a top-tier management team to handle logistics and cleaning, so you get both thoughtful design and professional support.brbrbrbrYou'll find soft, nice sheets (not the nylon nightmares other hosts offer up), good pillows, a nice mattress, thick towels, and Public Goods bath products. I also keep you stocked with coffee and a few small extras to make mornings feel less like punishment.brbrbrbrThis is a vintage Chicago building with the quirks to prove it: this space was originally the building engineers workshop, so even though they killed the soul of the space with the remodel, it has a great vibe. Ground floor level....yes, you may spot the occasional rogue cobweb despite my excellent cleaning team. But if you’re into character, comfort, and staying somewhere that doesn’t feel like an abused IKEA showroom... welcome home.brbrbrbrThere are four steps down into the unit, so it’s not great for guests with limited mobility. And yes, it's the ground floor of a 120-year-old building, so you will hear footsteps above. But also: you'll sleep well here. It’s quiet for being in the city. It’s comfy with just enough alarmingly green paint to make it have an opinion.brbrbrbrLocation:brbrbrbrThe flat is in Ravenswood, a peaceful, tree-lined neighborhood with it’s own vibe. You’re tucked into a quiet pocket of the city just a few blocks east of Damen Avenue. Walk 10 or so minutes and you’re on the Brown Line train (a super scenic trip that takes you straight into the heart of the city); there is also a METRA commuter station around the corner that goes into downtown. Once here, you'll find pockets of busier spots with great places to eat and a lovely grocery all within a nice walk.brbrbrbrParking:brbrbrbrI’ll say this, and really mean it: we are so well located with transit and ride share options you probably won’t need a car unless you are using it to get to Chicago. If you are insisting on it, there’s no designated parking spot. Street parking is generally available on our block and surrounding ones, though it can be a challenge later at night and you have to carefully watch out for zone restrictions that are here and there on the surrounding streets. Also, do a little refresher course in parallel parking before you are attempting to do it between strangers cars :-)brbrbrbrYour best bet SpotHero. It’s an app that lets you book a spot in advance and avoid the whole “circling for 40 minutes while reevaluating your life choices” thing. Put in Wolcott and Sunnyside to show the nearest spots.brbrbrbrAlso, a universal city tip: please read the signs. All of them. Chicago’s parking rules were clearly written by a sleep-deprived poet with a grudge.brbrbrbrExclusive perks:brbrbrbrGuests staying under 14 days get access to The Metropolitan Club, a members-only co-working and dining space on the 66th and 67th floors of the Willis Tower. Yes, it’s fancy. Yes, the view is outrageous. Yes, you can take your laptop and pretend to be someone who owns a watch that ticks.brbrbrbrGuest Access:brbrYou’ve got the entire flat to yourself. I promise you won’t somehow find your host staring into the refrigerator at 2 am. If you’re a smoker, please head off-property—outside the back door or in the courtyard garden still counts as “on property,” so plan accordingly. Vaping indoors also counts. (And no, that one clove cigarette you brought back from Berlin doesn’t get a pass.)brbrbrbrOther Things to Note:brbrQ: How do I get to [place] from here brbr A: Google Maps is your best friend. We’re near the Montrose Brown Line stop, which connects easily to everything. Need to drop in a search pin Use Wolcott and Sunnyside to explore the immediate area.brbrbrbrQ: When is check-in/check-out brbr A: Check-in is at 4pm. Check-out is at 11am. If you need a place to stash bags before or after, I can recommend a local luggage drop service. It never hurts to ask about early check-in…if we can, we do it. But a late checkout is always going to be a no, as our team of cleaners get their hustle on during the day so they can go home to their family at night.brbrbrbrQ: Do you have air conditioning or heat brbr A: We do! Radiator heat is supplied by the building (and turned on/off by folks who are not us with keys to the boiler room) and the space is also equipped with a forced air furnace so you can fine tune the heat. In warm months, a window AC unit will be installed starting mid-May. brbrbrbrWhy stay here brbrBecause I’ve done the hard part. I’ve figured out how to make a space that’s both beautiful and genuinely comfortable. A space where you can fall asleep under weird art and wake up to good light. A space that feels personal—but doesn’t have anyone’s toothbrush forgotten in the silverware drawer.brbrbrbrI’m the kind of host who wants to tell you where to get the best almond croissant and how to dodge Chicago parking tickets. I love sharing this place with people who notice details—who get joy from great sheets, unhinged bathroom paintings, and the quiet thrill of exploring someplace new.brbrbrbrBefore you book, our virtual front desk is available from 9am to 7pm CST to answer any questions you have. After you book, you’ll get access to that same virtual support during those hours plus a phone number where you can reach a real, live human being 24 hours a day—whether you’re locked out or just panicking about how the stove works.brbrbrbrHope you love it. brbrHope you come back.
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Exceptional(12)

$268.92

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Hotel

Large Unit Close to the Millennium Park! Parking!

Chicago, Illinois, United States

Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaurants, and shopping. Head to Navy Pier, Willis Tower, or Wrigley Field for iconic Chicago experiences. Shop ‘til you drops on the Magnificent Mile, which is within walking distance of the property. Experience Chicago-style pizza or Italian cuisine at a nearby restaurant.brbrThis listing is for a room within a hotel.brbr✦ Your room is 355 sq. ft, equipped with complimentary toiletries, standard quality 50-inch TV, available with Standard cable, and Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Fitness center is available.brbr✦ Paid parking lot – 1 space(s), available for $52 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per unit, per night, on a valid credit card. Amount varies between weekdays and weekends.brbr✦ The swimming pool is currently under maintenance and will remain closed until further notice
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Exceptional(2)

$257.04

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Hotel

Prime Location! Near Millenium Park, Shedd Aquarium, Willis Tower

Chicago, Illinois, United States

Explore iconic Windy City hot spots just minutes from this downtown propertybrbrThis listing is for a room within a hotel.brbr✦ Your room is 355 sq. ft, equipped with complimentary toiletries, standard quality 50-inch TV, available with Standard cable, and Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ Fitness center is available.brbr✦ Paid parking lot – 1 space(s), available for $52 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per unit, per night, on a valid credit card. Amount varies between weekdays and weekends.brbr✦ The swimming pool is currently under maintenance and will remain closed until further notice
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