Home Vacation Home Rentals By Owner In Ashland, OR

Showing 20 Of 72 Vacation Rentals
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Exceptional(5)

$445.09

/ Nightly
Private Vacation Home

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Ashland, Oregon, United States

Welcome to the Barclay-Klum House: A 2-bed, 1-bath gem, walking distance to Ashland`s vibrant downtown. brbrBedrooms: Queen bed in the main room, full bed in the secondbrBathroom: Large soaking tub & walk-in showerbrKitchen: Fully equipped gourmet kitchenbrOutdoor Space: Private, fully fenced yard with propane grill, hammock, & plenty of seatingbrExtras: Pack-n-play for kids, 55` Smart TV, & three off-street parking spotsbrbrPlease note: the lower unit is not accessible and may occasionally be occupied by friends or family. Reach out if you`d like to know whether the shared driveway will be in use during your stay.brbr*DISCOUNTED OSF TICKETS*brbrWanderLodges is proud to be an OSF Lodging Partner for the Oregon Shakespeare Festival’s 2026 season! As part of this special partnership, all guests with a confirmed reservation at any of our properties will receive an exclusive 20% discount code for OSF tickets in B and C sections—valid for the entire season!brPOLICY REMINDERS:br- Cancelations are dependent on the channel and rate you booked. For direct and standard rates: Cancellations made 5+ days before arrival, a full refund minus a $39 cancellation fee will be issued (non-refundable rates excluded). After that, only the cleaning fee will be refunded.br- Occupancy Limits: Guests agree to not exceed maximum occupancy stated in the listing. $15 per person, per night is charged after the first 4 guests in a reservation. Failure to notify WanderLodges of accurate occupancy may result in additional per person fees if applicable or up to/including reservation termination.br- Parties/Large Gatherings: All parties or occupancy issue creating gatherings are strictly prohibited at all WanderLodges properties, and guests agree to comply with all city, company, and fire code noise and use requirements.br- Pets/Service Animals: Pet friendly properties are subject to an additional $25 per pet/per stay cleaning fee. Pets must never be left unsecured or unattended at the property, and WanderLodges must be notified at time of booking of pet requests. As always, we are happy to accommodate registered service animals of our guests.br- Smoke Free: As a reminder, all WanderLodges properties are smoke and vape free. Smoking indoors, within 10 feet of an entry, or anywhere on the property will incur an additional $250 fee.br- Quite Hours: Considered between 10PM and 8AM. Please keep noise to a minimum in consideration of neighbors. Noncompliance of this will incur a $100 fee per incident, and/or a request to vacate.br- Damages: All damages must be reported to WanderLodges as soon as possible. By booking, guests agree to financial responsibility for all damages due to gross negligence and up to an additional $500 in cleaning fees for negligent use.br***** By booking, guests are agreeing that they are of 18 years of age or older, legally able to agree to these terms, and any minors part of the itinerary will always be accompanied by a parent or guardian. *****
Bed 2

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Bath 1

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Sleep 4

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Exceptional(31)

$757.88

/ Nightly
Private Vacation Home

The Ashland Social | Main House

Ashland, Oregon, United States

Luxury 3BR escape with pool awaits near the Oregon Shakespeare Festival. Indulge in refined living with 3 king beds, ensuite bathrooms in every bedroom, and two queen pull-out couches for up to 10 guests.brbr★HOME OVERVIEW★brWelcome to our large elegant home, featuring two stunning master bedrooms. All three bedrooms have king sized beds and en suite bathrooms making it the perfect friends and family getaway!brbr★SLEEPING ACCOMMODATIONS★brbrWe can sleep 10 people total!brbrBedroom 1: King Bed, ensuite bathroom with jetted tub, 55 tvbrBedroom 2: King Bed + Queen fold out couch, ensuite bathroom with french doors that open to the pool area, 55 tvbrBedroom 3: King Bed, ensuite bathroom, 55 tvbrLiving Room: Queen fold out couchbrbrThe spacious living room, dining room, and kitchen provide ample space for enjoying time with friends and family.brbr★FIVE STAR AMENITIES★brbrStep outside to our inviting outdoor area, complete with a large table and chairs, a bistro table, a barbecue, a heat lamp, and plenty of comfortable seating. Relax in our hot tub or seasonal pool with loungers. (Pool is open year round but only heated from Memorial Day to Labor Day). brbrbr★LIVING AREA★brRelax on our large (111 by 111) sectional sleeper sofa and stream your favorite shows on our Smart TV (Roku) or just enjoy the fireplace that turns on with a flick of a switch. Enjoy access to Netflix, Hulu, Prime Video, and Apple TV by simply entering your password. br‎br★KITCHEN★brThe kitchen is a chef's dream. You'll be amazed at how well stocked this fully loaded kitchen is whether you want to prepare a simple breakfast or spend the day cooking a feast. From every size pot and pan to even some rare spices this kitchen is perfect for your friend and family getaway. Our coffee and tea bar has everything you need to get going in the morning. Enjoy a 2-in-1 coffee maker with both Keurig and drip options.brbr★DINING★brYou've got options! The formal dining room has a large table that seats 6 comfortably (or squeeze 8 in!). The breakfast nook seats 4 and kitchen island seats 2. On our better weather days you can enjoy a large outdoor table for 6 or a small bistro table for 2. br‎br★BATHROOMS★brThere are 3.5 bathrooms total. Each bedroom has an ensuite and there is a half bath off the living room. There are 2 bathtubs (one large jetted tub in the master bedroom and the second one in the other upstairs bedroom). Towels, shampoo, conditioner and body wash are provided.brbr★GAME ROOM★brLevel up your stay in our newly added game room! Challenge friends and family to ping pong matches, dive into your favorite video games with 2 brand new arcades. Perfect for evenings of entertainment, laughter, and friendly competition.brbr★LAUNDRY ROOM★brThere is a full sized washer and dryer in the laundry room upstairs.brbr★PARKING★brThere is one spot in front driveway for your car and ample street parking.brbr★RESTAURANTS & BARS★brThe best of the best on the Ashland Plaza is a 4 minute drive away!brbr★HEATING & AC★brThe house has a central heat and AC with 2 thermostats (one on each floor). brbrFor safety, there is a ring doorbell at the front door. It is active 24/7. Video and sound recording is motion activated. The home is also equipped with a decibel monitoring sensor located inside and outside of the home. It is 100% privacy compliant and is required on this property. Tampering with or disabling the ring doorbell and noise monitoring sensor will immediately cancel the reservation.brbrExperience the ultimate in luxury and relaxation at our retreat – book your stay todaybrbrIMPORTANT REMINDERS:br- You will be asked to sign a rental agreement.br- There is an adjacent studio that is rented separately. Studio guests have no access to the backyard and amenities ensuring your complete privacybr- Pool maintenance is scheduled every Thursday. During this time, our dedicated team will be working diligently to ensure the pool is in top-notch condition for your safety and enjoyment. The maintenance process typically takes approximately 1 hour and 45 minutes, during which guests will need to exit the pool. Please also note that after chemicals are added, it is not recommended to swim for approximately 24 hours to ensure proper water balance and safety.br- Garden maintenance occurs on Wednesdays. Our team ensures the garden remains in excellent condition for your enjoyment.brbrCancellation Policy: 50% refund up until 60 days prior to arrival. No refund if cancelled within 60 days.brbrEarly Check-In / Late Check-Out Options:br- We may be able to accommodate an early check-in starting at 1:30 PM or a late check-out until 1:30 PM for an additional fee of $120.00, subject to availability and scheduling.br- To help us coordinate with our cleaning and operations teams, requests must be made at least 1 day in advance and are not guaranteed until confirmed by management.br- For guests needing significantly earlier arrivals or later departures, we recommend booking the previous or following night to ensure uninterrupted access to the property.br- Unapproved late checkouts will incur an additional charge of $300.
Bed 3

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Bath 4

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Sleep 10

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Exceptional(12)

$845.4

/ Nightly
Private Vacation Home

The Ashland Social | Entire Estate

Ashland, Oregon, United States

Welcome to our luxurious and tranquil retreat, featuring two stunning master bedrooms. One bedroom boasts a jetted tub in its en suite bathroom, while the other features French doors leading out to the pool area.brbr★HOME OVERVIEW★brWelcome to our large, luxurious and tranquil retreat, featuring two stunning master bedrooms. All four bedrooms have king sized beds and en suite bathrooms making it the perfect friends and family getaway! brbr★SLEEPING ACCOMMODATIONS★brbrWe can sleep 12 people total! brbrBedroom 1: King Bed, ensuite bathroom with jetted tub, 55 tvbrBedroom 2: King Bed + Queen fold out couch, ensuite bathroom with french doors that open to the pool area, 55 tvbrBedroom 3: King Bed, ensuite bathroom, 55 tvbrBedroom 4: King Bed, french doors to the backyard, small tvbrLiving Room: Queen fold out couchbrbrThe spacious living room, dining room, and kitchen provide ample space for enjoying time with friends and family.brbr★FIVE STAR AMENITIES★brStep outside to our inviting outdoor area, complete with a large table and chairs, a bistro table, a barbecue, a heat lamp, and plenty of comfortable seating. Relax in our hot tub or seasonal pool with loungers, or hang out in our game room with 2 arcades and a ping pong tale. (Pool is open year round but only heated from Memorial Day to Labor Day). brbr★LIVING AREA★brRelax on our large (111 by 111) sectional sleeper sofa and stream your favorite shows on our Smart TV (Roku) or just enjoy the fireplace that turns on with a flick of a switch. Enjoy access to Netflix, Hulu, Prime Video, and Apple TV by simply entering your password. br‎br★KITCHEN★brThe kitchen is a chef's dream. You'll be amazed at how well stocked this fully loaded kitchen is whether you want to prepare a simple breakfast or spend the day cooking a feast. From every size pot and pan to even some rare spices this kitchen is perfect for your friend and family getaway. Our coffee and tea bar has everything you need to get going in the morning. Enjoy a 2-in-1 coffee maker with both Keurig and drip options. There is also a kitchenette in the 4 (yellow) bedroom, which is the adjacent studio so you can have a cup of coffee before joining the rest of the group. brbr★DINING★brYou've got options! The formal dining room has a large table that seats 6 comfortably (or squeeze 8 in!). The breakfast nook seats 4 and kitchen island seats 2. On our better weather days you can enjoy a large outdoor table for 6 or a small bistro table for 2. The 4th bedroom (studio unit) has a small table for 2. br‎br★BATHROOMS★brThere are 4.5 bathrooms total. Each bedroom has an ensuite and there is a half bath off the living room. There are 2 bathtubs (one large jetted tub in the master bedroom and the second one in the other upstairs bedroom). Towels, shampoo, conditioner and body wash are provided.brbr★GAME ROOM★brLevel up your stay in our newly added game room! Challenge friends and family to ping pong matches, dive into your favorite video games with 2 brand new arcades. Perfect for evenings of entertainment, laughter, and friendly competition.brbr★LAUNDRY ROOM★brThere is a full sized washer and dryer in the laundry room upstairs.brbr★PARKING★brThere is one spot in front driveway for your car and ample street parking.brbr★RESTAURANTS & BARS★brThe best of the best on the Ashland Plaza is a 4 minute drive away!brbr★HEATING & AC★brThe house has a central heat and AC with 2 thermostats (one on each floor). The 4th adjacent bedroom has a window AC unit, wall heat as well as heated floors. brbrFor safety, there is a ring doorbell at the front door. It is active 24/7. Video and sound recording is motion activated. The home is also equipped with a decibel monitoring sensor located inside and outside of the home. It is 100% privacy compliant and is required on this property. Tampering with or disabling the ring doorbell and noise monitoring sensor will immediately cancel the reservation.brbrExperience the ultimate in luxury and relaxation at our retreat – book your stay todaybrbrIMPORTANT REMINDERS:br- You will be asked to sign a rental agreement.br- Pool maintenance is scheduled every Thursday. During this time, our dedicated team will be working diligently to ensure the pool is in top-notch condition for your safety and enjoyment. The maintenance process typically takes approximately 1 hour and 45 minutes, during which guests will need to exit the pool. Please also note that after chemicals are added, it is not recommended to swim for approximately 24 hours to ensure proper water balance and safety.br- Garden maintenance occurs on Wednesdays. Our team ensures the garden remains in excellent condition for your enjoyment.brbrCancellation Policy: 50% refund up until 60 days prior to arrival. No refund if cancelled within 60 days.brbrEarly Check-In / Late Check-Out Options:br - We may be able to accommodate an early check-in starting at 1:30 PM or a late check-out until 1:30 PM for an additional fee of $150.00, subject to availability and scheduling.br - To help us coordinate with our cleaning and operations teams, requests must be made at least 1 day in advance and are not guaranteed until confirmed by management.br - For guests needing significantly earlier arrivals or later departures, we recommend booking the previous or following night to ensure uninterrupted access to the property.br - Unapproved late checkouts will incur an additional charge of $300.
Bed 4

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Bath 4

Bath

Sleep 12

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$887.1

/ Nightly
Private Vacation Home

The Gem and Cottage of Ashland, Hot tub, Views

Ashland, Oregon, United States

Magnificent Hilltop Getaway with Incredible Views (sleeps 14.)brCome enjoy this oasis on the outskirts of the magical town of Ashland. This gorgeous home is perched above town on 3 acres offering some of the most epic mountain views and best sunsets in the valley.brThis special place pampers you with 5 bedrooms, 4 bathrooms, gas fireplace, hot tub, copper cold plunge, outdoor pool and multiple decks to take in the breathtaking views. Located 7 minutes from downtown Ashland.brbrThere are 2 levels to the home. Upstairs hosts the main living room, kitchen, and dining room, all in an open and airy layout perfect for connecting with your family. Three bedrooms sit down the hallway, one with a queen bed and two with a king bed, the master has an attached bathroom and a smart TV in it. Downstairs is one bedroom with a private entrance with a queen bed, a double futon and a separate bathroom, along with a laundry area with a washer and dryer. brbrThe outside studio has a queen bed and a couch bed that sleeps two, with a smart TV, kitchen, and big soaking tub for those who want a bit more privacy and a fully stocked separate space.brbrThe Gem is perfect for all seasons. Come enjoy the pool and gorgeous outdoor areas in the summer or come sit in the hot tub overlooking the snowy mountains and cozy up by the fire in the winter. Spring and fall are glorious times to be here too! It is perfect for romantic getaways, family celebrations, spending time with friends or enjoying some solo time to retreat and relax.brbrOverlooking beautiful Ashland, Southern Oregon’s home for theater and the arts, Gem House is a luxury home that integrates the natural elements of the land with the amenities that make for a fun, one-of-a-kind vacation stay. Greet the day from the sun porch, swim in the custom designed pool, dip in the copper cold plunge bathtub, and then settle in for a long soak in the 6-person spa, all with epic views of the valley and Mount Ashland. There are decks and lounging areas everywhere, and with vaulted ceilings and picture windows throughout, you are never far from a stunning view.brbr• Indoor/Outdoor living at its finestbr• Swimming pool, hot tub, copper cold plungebr• Multiple decks with numerous lounging optionsbr• Spacious chef’s kitchenbr• Home theater system with retractable 8-foot screenbr• Premium Wi-Fi and Smart TVsbrbrStep into the great room at the heart of Gem House. The chef in you will delight in the fully appointed kitchen with gas cooking island, granite countertops and spacious refrigerator. Steps away is the living room with sectional sofa, fireplace, and home theater with a retractable 8-foot screen for an epic viewing experience. The bay-windowed dining area seats six with room to stretch. Gem House boasts beautiful bedrooms, with king beds, queens, one with a double futon and private entrance, full baths, and laundry.brbr* We have hosted on different sites from 2022-2026 and got over 45 incredible reviews during that time.brbr“Stunning home and location. The grounds of this property are so well kept and so beautiful. Inside is clean and comfortable with incredible views. Love all the yogi decor and kitchen is well stocked. The hot tub and pool are perfect. We stayed here for my husband's 30th birthday to attend Oregon Shakespeare Festival. It's an easy 10 min drive into town for shows, restaurants and shopping. And ever quicker to get onto I-5. We had such a lovely time and would stay again in a heartbeat.”brAlisonbrPosted: 6/7/2023brbr**The owners may be on the property and stay in a tiny home at the back of the property. We want our place to feel like your own so we are very quiet and you won't even know we are there.
Bed 5

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Bath 4

Bath

Sleep 14

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Exceptional(89)

$427.41

/ Nightly
Private Vacation Home

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

Ashland, Oregon, United States

Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from OSF, theaters, Plaza and Downtown. brbrVICTORIAN ROSE (2 BDRM-2 BATH-Sleeps 6)brLet this beautiful cottage in a historic home fill you with a sense of comfort and luxury. This 875 square feet home has two bedrooms, each with a queen bed. A queen sleeper sofa in the living room can sleep another two people (or use the queen air mattress instead). One of the bedrooms has an attached bathroom with a walk-in shower. The second bathroom is newly renovated and has a combination tub-shower and the expansive kitchen is fully stocked to cook elaborate or simple meals. Enjoy your coffee/glass of wine in the separate dinning room, on the front porch overlooking the garden, or simply step out to the many neighborhood restaurants and cafes. A private back porch affords additional quiet reading or dining space while looking out into the surrounding garden. brbrThere are a few steps (2/3) to enter the house, but once inside all living areas are on the same level. Park on the property and walk to the local interests and the fabulous restaurants just steps away. We provide fine linen and towels for the use of our guests. Books, spanning a range of genres, free internet/wifi and cable TV are provided as well. Ashland Food Co-Op is less than five minutes away if you need to pick up groceries or additional supplies. A famous local coffee house and landmark restaurants are just steps away. brbrThe Victorian Rose was built in 1901, in the Folk Victorian style. It is on the National Register of Historic Homes. brbr*Our calendar is current, book with confidence. Ask about our MONTHLY rental for off peak season (November to April).brbrOur other listings:brBlue Hyacinth is our newer house, built to be architecturally similar to the older houses prevalent in Ashland. The house, 3 BDRM-2 BATH, sleeps 8 and can be rented at listing 819212. brbrGroups larger than 8 can book both houses depending on availability.brbrSee www.blossomviewcottages.com for more information.brbrCancellation Policy: The entire amount is refunded if cancelled sixty (60) days prior to arrival date. If we can re-book your dates, all but the security deposit is refunded. brbr** Prices subject to change until confirmed.brbrPA#15-797
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Bath 2

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Sleep 6

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Exceptional(76)

$518.48

/ Nightly
Private Vacation Home

BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

Ashland, Oregon, United States

BLUE HYACINTHbr brWelcome to the Blue Hyacinth, a lovely 3 BDRM-2 BATH house, at Blossom View Cottages. We are located in the historic railroad district, three short blocks (less than half a mile) to downtown and theaters (OSF), so you can walk everywhere from this lovely home. brbrCANCELLATION POLICY: For our three bedroom house, the entire amount is refunded if cancelled sixty (60) days prior to arrival date. If we can re-book your dates, all but the security deposit is refunded. brbrDESCRIPTION: This is a luxurious and comfortable home. Two bedrooms and one bathroom are located upstairs, all other living areas (one bedroom, den, bathroom,kitchen,family room) are located downstairs. Enjoy wine/coffee on one of the front porches (there are two) while looking out at the gardens or dine/relax under the stars on the back patio. The fully stocked kitchen lends itself to simple or sumptuous meals or you can walk to Ashland’s finest restaurants on A-Street, 4th Street and Downtown. The Ashland Food Co-op is less than two blocks away. The house itself is surrounded by colorful gardens. brbrEach bedroom is furnished with a queen bed and one of the upstairs bedrooms also has a twin bed. The den has a very comfortable queen sofa bed. Books from a range of genres, internet and cable TV are provided. Our home is furnished with quality bed linens and towels for the use of guests. brbrCANCELLATION POLICY: For our three bedroom house, the entire amount is refunded if cancelled sixty (60) days prior to arrival date. If we can re-book your dates, all but the security deposit is refunded. brbrOur other listings:brVictorian Rose: This is the other house on the property. See listing 819214 for the 2 BDRM-2 BATH, which sleeps 6.br brLarger groups can book both houses depending on availability.brbrSee www.blossomviewcottages.com for more information. brbr*Our calendar is current, book with confidence. Ask about our MONTHLY rental for off peak season (November to April).br** Prices subject to change until confirmed.brPA#15-797
Bed 3

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Bath 2

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Sleep 10

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Exceptional(75)

$522.1

/ Nightly
Private Vacation Home

Ashland Lodge w/ Lake Views & Game Room Loft

Ashland, Oregon, United States

Make memories that last a lifetime by booking this extravagant Ashland home, a 4-bedroom, 3-bath vacation rental with plenty of offer! The property boasts an impressive and spacious interior with a full kitchen and game room loft. Spend days barbecuing on the private patio enjoying spectacular views of the nearby lake or relaxing in the fresh mountain air. With natural surroundings and a prime location, this gem lets you have your pick of outdoor adventure!brbr-- THE PROPERTY --brbr3,186 Sq Ft | Outdoor Fireplace | 2 Bedroom SuitesbrbrThis vacation rental home offers an elegant-yet-rustic accommodation option for a family or group of friends looking for a tranquil escape to the Pacific Northwest!brbrBedroom Suite 1: King Bed | Bedroom Suite 2: King Bed | Bedroom 3: Queen Bed, Twin Bed | Bedroom 4: 3 Twin Bunk Beds (No Heat or A/C)brbrOUTDOORS: Private patio, stone fireplace, gas grill, 2 kayaks, snowshoes, lake viewsbrINDOORS: Open floor plan, 2-story high vaulted ceilings, authentic wood accents, 65” flat-screen TV, DVD player w/ movie collection, wood-burning fireplace, ping pong table, foosball, board gamesbrKITCHEN: Fully equipped w/ stainless steel appliances, island wet bar, drip coffee maker, tea kettle, mixer, dishwasher, 12-seat banquet-style dining tablebrGENERAL: Free WiFi (Starlink), in-unit laundry machines, central heating & A/C, linens & towels, private entrancebrFAQ: 2 external security cameras (facing out), step-free access, interior stairsbrPARKING: Gravel driveway (ample parking spaces provided)brbr-- THE LOCATION --brbrAREA ACTIVITIES: Sailing (marina 0.25 miles away), boating, kayaking/canoeing, fishing, mountain biking, hiking, wildlife watching, birdwatchingbrGET OUTDOORS: Howard Prairie Lake Resort's Marina (0.2 miles), Howard Prairie City Park (1.9 miles), Cascade-Siskiyou National Monument (20.0 miles), North Mountain Park (24.0 miles), Lithia Park (25.2 miles)brFAMILY FRIENDLY: ScienceWorks Hands-on Museum (23.1 miles), Oregon Shakespeare Festival (24.5 miles), Crater Lake Zipline (29.7 miles)brADVENTURE TRIPS: Mt Ashland Ski Area (39.8 miles), Crater Lake National Park (68.6 miles)brAIRPORT: Rogue Valley International-Medford Airport (39.7 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowed. Please do not inquirebr- Must be at least 25 years old to bookbr- No events, parties or large gatheringsbr- Additional fees and taxes may applybr- NOTE: Due to the property’s rural location, cell phone reception may be spottybr- NOTE: Bedroom 4 does not have heat or air conditioning. Please plan ahead with your own bedding for this roombr- NOTE: While this property features step-free access, stairs are required to access some bedroomsbr- NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the garage facing the driveway, and 1 camera is on the back patio facing the pond. They do not look into interior spaces. The cameras record video when activated by motion
Bed 4

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Bath 3

Bath

Sleep 13

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