Vacation Rentals By Owner In Chesapeake, VA

Enjoy you stay in four large bedroom, Two and half bath, dining room, eat-in kitchen, extra large bonus room and large family room home. Close to interstate, River’s Casino and many restaurants and golfing. Within 25 minutes to Va Beach boardwalk, and Norfolk Oceanview beach Near downtown Portsmouth, Norfolk ,Hampton, Suffolk and Newport News.

Spacious tranquil 4 bedroom family home near everything

Chesapeake, Virginia, United States

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Exceptional(2)

$163.92

Super comfy and clean. Bring your food and clothes! The rest is here.brEnjoy 2 bedrooms . 1 King and 1 Queen bedsbrWork space in office/ baby room. We are proud of our home in a older quiet neighborhood close to interstate food and shopping. We are a pet friendly home.

Southern Charm Warm and WelcomenEntire home hosted by Annetten4 guests

Chesapeake, Virginia, United States

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Sleeps

$81.97

Take a break and unwind at this peaceful and meticulously renovated, fully furnished studio guest suite in an extremely quite neighborhood. Room features; kitchenette, king size bed for couples, sleeper sofa for additional guest, 55 Inch Sony TV, Huge Walk-In Closet, Fridge, New Over-The-Range Microwave, New Washer/Dryer, Full Bathroom, Glass Computer/Reading Desk, Additional Portable Heater, Free Street Parking Only and much more...brPlease book at least 5 days before check in to allow for room prep.brMinimum Of 1 Month Stay Required and br*Minimum Of 1 Month Lease & & Background Check before lease signing.br*Sorry No Pets Allowedbr*Price Is Firm! No Haggle!! Huge Additional Monthly Discount Already AppliedbrTHINGS NOT PROVIDED: brStove, Dishwasher, Garbage Disposal, Ceramic Dishes or Glasses, Towels, Silverware, Cups, Napkins, Bath Tissues, Toiletries, Spices, Cookware of any kind. Guests can bring theirs as well as portable cooking appliances etc.

Apartment

GORGEOUS 1 BEDROOM WITH FREE WIFI & STREET PARKING

Chesapeake, Virginia, United States

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Treat yourself to the majestic experience you deserve by booking Jo's Bungalows. This 4 bedroom, 2bathroom facility sleeps 8 individuals (consisting of 2queen-sized beds 1 Full, 1 Twin & 1 Futon) . The facility includes a full kitchen, on-site washer, dryer, office space, free Wi-Fi, 4 smart TVs, and a fenced in backyard (including mood lights, outdoor living area, dining area, heater, firepit, grill, and playground). This property is moments away from several 24/7 gyms, hospitals, restaurants, stunning walking/biking trails, shopping areas, amusement parks, museums, libraries, 3 breathtaking beaches (oceanfront, outlook beach & ocean view) and so much more! All it's missing is YOU!!

Luxurious 4 bedroom 2bath Bungalow w/ Private Backyard Oasis

Chesapeake, Virginia, United States

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Bath

Sleeps

Exceptional(1)

$120.51

Forget your worries in this spacious serene home. Near major interstates, shopping, restaurants and hospitals. Great neighbors in quiet neighborhood. Come be yourself or bring the family. This place is sure to meet your needs. About 20 min from VB Oceanfront. Full backyard to enjoy family or entertain friends.

The Full House

Chesapeake, Virginia, United States

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$288.5

Convenient location to Norfolk waterside.20 minutes from Virginia Beach oceanfront . Free curbside parking. Nice and clean, quite plenty of room. Front porch.. local restaurants supermarkets within walking distance.

Apartment

Historical section of Chesapeake. Propertie nice and groomed quiet neighborhood.

Chesapeake, Virginia, United States

Bed

Bath

Sleeps

Exceptional(5)

$460.83

Venture out to Virginia and stay at this centrally located Chesapeake home near Elizabeth River. This 4-bedroom, 3-bath vacation rental boasts an inviting interior with Smart TVs, a cozy fireplace, a pool table, and more. Bring your bike for rides around the area, get retail therapy at the Chesapeake Square Mall, explore nature at Portsmouth City Park or the Chesapeake Arboretum, or visit the Chrysler Museum of art. Then, test your luck at Rivers Casino Portsmouth!brbr-- THE PROPERTY --brbrFree WiFi | Washer + Dryer | Bikeable + Walkable AreabrbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Full Bed | Bedroom 4: Full Bed | Living Room: Queen Sleeper Sofa, Twin DaybedbrbrOUTDOOR LIVING: Deck, private yard, boating, close to marina & beachesbrINDOOR LIVING: Smart TV w/ cable, en-suite bathroom, fireplace, walk-in closet, jetted tub, shower, high chair, dining tablebrKITCHEN: Refrigerator, microwave, stove/oven, dishwasher, garbage disposal, coffee maker, toaster, toaster oven, ice maker, cooking basics, dishware/flatwarebrGENERAL: Central A/C + heating, ceiling fans, linens/towels, complimentary toiletries, hair dryer, hangers, iron/board, trash bags/paper towelsbrFAQ: 8 external security cameras (facing outwards)brACCESSIBILITY: 2-story home, 5 steps required for entry, internal steps required for bedroom access, accessible-height toilet, grab rails in bathrooms + showerbrPARKING: Garage (1 vehicle), driveway (4 vehicles), free street parking (first-come, first-served), RV/trailer parkingbrbr-- THE LOCATION --brbrOUTDOOR RECREATION: Stonebridge Landing Park (0.2 miles), Western Branch Park and Sports Park (2 miles), Elizabeth Manor Golf & Country Club (3 miles), Portsmouth City Park - Elizabeth River Access (3 miles), Chesapeake Arboretum (15 miles), Chesapeake City Park (17 miles)brLOCAL ATTRACTIONS: Chesapeake Square Mall (1 mile), Norfolk Naval Shipyard (7 miles), Chrysler Museum of Art (10 miles), Virginia Aquarium & Marine Science Center (28 miles)brVISIT NEARBY: Portsmouth (7 miles), Norfolk (9 miles), Newport News (25 miles), Virginia Beach (26 miles), Richmond (92 miles)brAIRPORT: Norfolk International Airport (18 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- Absolutely no smoking or vapingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 2-story home requires 5 external steps for entry and internal steps for access to all bedroomsbr- NOTE: Your safety matters. This property features 8 exterior security cameras. 1 camera is located on the garage exterior facing the sidewalk, 1 camera is located near the front entrance facing the front entry, and 2 cameras are located on the back exterior facing the backyard. Additionally, there is a camera located on the exterior on each side of the home facing out. They do not look into any interior spaces. The cameras record video and sound when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detected

Spacious Chesapeake Home w/ Pool Table!

Chesapeake, Virginia, United States

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Select Dates for Price

This home was hand built by the owner, a professional builder. It is set back 1/4 mile drive. SUV or truck is best, to drive down, but we drive a car down almost everyday. Private and serene country home. You will have 5 bedrooms, 3.5 bathrooms, large kitchen and open floor plan. A large screened in porch to watch the hummingbirds and relax by the fire at night. This will be a stay you never forget! It is our personal home we love to share with others, while visiting family during the summer. Please enjoy our home and care for it as you would your own. brWe are in the country! You will hear the frogs croaking at night, and see some occasional bugs and lizard friends outdoors. We look forward to having you! We have one outdoor security camera at the side door.

Beautiful custom built home in the country

Chesapeake, Virginia, United States

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$321.85

Your group will enjoy the convenience of being centrally located in the Greenbrier area of Chesapeake in this well appointed, spacious ranch style home. This property has three well appointed bedrooms, 2.5 baths, fully equipped eat-in kitchen, dining room - and a flex space we like to call The Green Room. There is off-street parking for up to four vehicles and a huge backyard. All located within minutes of major highways, the Virginia Beach Oceanfront, hospitals, shopping, eateries, entertainment and military bases.

Beautifully appointed, spacious ranch style home located in Greenbrier!

Chesapeake, Virginia, United States

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$150.47

This is a peaceful, centralized, greatly furnished family sized home located in a highly sought-after community in the heart of Chesapeake city in Virginia. This beautiful home is just 5 - 10 minutes drive away from major shopping centers and parks, about 25 minutes drive to Virginia Beach and Norfolk International Airport. It has many attraction centers, including the Chesapeake Arboretum and Chesapeake Planetarium and Virginia Aquarium. And 4 minutes drive to Chesapeake Regional Healthcare.

Very Decent 4 bedroom / 2 full bath. Located within the heart of the City.

Chesapeake, Virginia, United States

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Bath

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$158.17

This quiet neighborhood is a great place to relax and enjoy your stay. It has a private entrance, privacy fenced in shared backyard. The left side of the backyard is shared with an RV separate from the house. Guests have plenty of space in the back to enjoy. There is always plenty of parking right in front of the house for convenience. Downtown Portsmouth and Norfolk are within 7 miles away. The Virginia Beach oceanfront is only 35 minutes away. Portsmouth city park is 5 minutes away and has a boat ramp for those who are interested in any water activities. We welcome long term stay for military families, corporate stay and family getaway.brThe spacebr“We’re taking extra care to disinfect frequently touched surfaces between reservations.”brbrJust minutes from downtown Norfolk, Rivers Casino and Hampton Roads attractions. The entire house is yours for your weekend stay or a week getaway. The house has all the essentials you need to make you feel at home. This house comfortably sleeps 6 guest. Look at the pictures to make sure it perfectly accommodates your guest size and sleeping arrangement.brbr***We welcome long term rental. There is an additional cleaning fee required for our long term stays, as we schedule a mid stay clean with our cleaning staff to keep the home fresh***brGuest accessbrGuest have the luxury of using the entire space as needed. There is adequate parking in the driveway and on street parking is allowedbrOther things to notebrHere are some attractions and restaurants to visit during your stay:brbrRivers CasinobrWaterside District downtown NorfolkbrGreat wolf LodgebrBush GardensbrWater CountrybrMotor worldbrApexbrOcean breeze WaterparkbrBotanical GardensbrWilliamsburg outletsbrNorfolk outletsbrOceanview BeachbrBuckroe BeachbrFort MonroebrVirginia beach oceanfrontbrNorfolk Naval basebrPortsmouth Naval basebrPortsmouth City ParkbrbrRestaurantsbrBlue MoonbrGrainbrSaltinsbrBaxtersbrGranby Street Restaurants and BarsbrHair of the DogbrCork & Co.brCanvasbr456 FishbrCuban IcebrSaffron Indian BistrobrGrace O'Malley'sbrFreemason AbbybrBenny's DamatosbrByrd and Baldwin Bro's Steakhousebr1865 Brewing Co.

A Quiet Chesapeake Escape! Close to Rivers Casino!

Chesapeake, Virginia, United States

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$277.64

Plan your next Chesapeake getaway and stay at this charming vacation rental home! This 2-bedroom, 1-bathroom guest house provides everything you need for your stay, including a well-equipped kitchen and a porch with outdoor seating. Spend your days checking out shops and restaurants at Chesapeake Square Mall, strolling through Oak Grove Lake Park, or visiting the sandy shores of Virginia Beach. After a day spent exploring the area, head back to relax on the couch with a movie on the Smart TV.brbr-- THE PROPERTY --brbrCovered Porch | Free WiFi | ~26 Mi to Virginia BeachbrbrBedroom 1: Queen Bed | Bedroom 2: Queen BedbrbrINDOOR LIVING: Smart TVs w/ cable, dining table, ceiling fanbrOUTDOOR LIVING: Deck, outdoor seatingbrKITCHEN: Microwave, coffee maker, tea kettle, toaster, blender, cooking basics, dishware & flatware, spicesbrGENERAL: Linens & towels, central air conditioning, complimentary toiletries, washer & dryer, hair dryer, iron & ironing board, hangers, trash bags & paper towelsbrFAQ: Stairs required to access, homeowner on-site (main house), 1 exterior Ring security camera (facing guest house), fire pit & grill unavailablebrPARKING: Driveway (2 vehicles), free street parking (first-come, first-served)brbr-- THE LOCATION --brbrDINING & SHOPPING: Chesapeake Square Mall (1.0 miles), Harbour View Marketplace (5.8 miles), MacArthur Center (9.4 miles), Greenbrier Mall (17.8 miles)brOUTDOOR RECREATION: Portsmouth City Park (3.7 miles), Paradise Creek Nature Park (7.5 miles), Elizabeth River Park (9.0 miles), Oak Grove Lake Park (16.3 miles), Chesapeake Arboretum (16.8 miles), Great Bridge Lock Park (17.7 miles), Chesapeake City Park (18.9 miles), Pleasure House Point Natural Area (22.0 miles), First Landing State Park (25.2 miles), Virginia Beach Fishing Pier (26.9 miles), Cape Henry Lighthouse (29.8 miles)brMILITARY BASES: Norfolk Naval Shipyard (6.8 miles), Little Creek (17.7 miles), Langley Air Force Base (23.9 miles), Naval Air Station Oceana (28.3 miles), Dam Neck (29.7 miles), Fort Story (32.5 miles)brVISIT NEARBY: Portsmouth (7.7 miles), Norfolk (9.2 miles), Virginia Beach (26.3 miles)brAIRPORT: Norfolk International Airport (18.6 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 allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your staybr- NOTE: Your safety matters. This property features 1 exterior Ring security camera located on the main house facing the guest house. This camera does not look into any interior spaces. The camera records video and sound when activated by motionbr- NOTE: The fire pit and grill are not available for guest use

Bright Chesapeake Home Near Shopping & Dining

Chesapeake, Virginia, United States

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Bath

Sleeps

Exceptional(12)

$307.19

Enjoy a great experience in this newly renovated home in a wonderful family friendly neighborhood. Just a 20-30 min drive to NOB, Portsmouth Naval Shipyard, Oceana, and VB Oceanfront. 5-10 min to Chesapeake Regional Hospital. Brand new comfortable furniture and 50” flat screen TV’s in every bedroom. First room has private bathroom, small walk-in closet and king size bed, nightstand with charging doc,TV. Seond bedroom is complete with TV, Queen bed two night stands. New appliances and Closet with hangers. Third bedroom has a Twin XL with nightstand and TV.Top of the line LG front load washer and dryer make this place hard to beat, with Stocked Laundry detergent and Deliquiate items bag for washing, and Dryer sheets. Our goal is to provide a comfortable clean environment in a cozy peaceful atmosphere. The Kitchen is stocked with all essentials with spice cabinet, coffee, creamer, and sugars. K-cups provided and Filters for Potted Coffee provided. Enjoy the treats left behind for late night snacks.

Townhome Newly renovated in GreatBridge, Chesapeake, ⭐️⭐️⭐️⭐️⭐️ on another site

Chesapeake, Virginia, United States

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Bath

Sleeps

Exceptional(21)

$213.76

Enjoy a peaceful stay at this lovely 3-bedroom house nestled in the Great Bridge area of Chesapeake. The bedrooms feature a King size bed, queen bed, and two twin beds (with the option to make it a single king) , perfect for a variety of guests. With amenities like WiFi, AC, full kitchen, covered/screened-in back patio, large fenced in yard and a washer/dryer machine, your comfort is guaranteed. The two bathrooms offer convenient shower facilities. Feel at home in this fantastic property and make the most of your stay in Chesapeake. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out.brbr Attractions: Virginia Beach boardwalk-24.5 miles. Naval Station, Norfolk- 8.7 miles. Bush Gardens Williamsburg- 64.5 miles.

3-bedroom home away from home in fabulous Chesapeake, Virginia.

Chesapeake, Virginia, United States

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Bath

Sleeps

Exceptional(6)

$271.03

Welcome to this beautifully kept 3-bedroom newly renovated home in Chesapeake. The high end mattresses provide a beautiful sleep and our professional housekeeping will make sure you enjoy your stay every time. Your very family friendly experience includes:brbr- Fully fenced backyard ⛩br- Free parking br- Laundry Room br- Private Desk Space br- Speedy Wi-Fi 250 mbps br- 1 Queen bed, 1 Full size bed, 2 Twin Size Beds br- 42 inch Roku Smart TV (Living Room)br- 40 Inch Roku Smart TV (Main Bedroom)brbrThe spacebr Kitchen- Was recently renovated with new appliances, quartz countertops. Its fully equipped with a range oven/stove, microwave, dishwasher, coffee maker (Keurig), toaster, pots and pans, and many essential cooking and dining utensils. Ideal for longer stays.brbr Dining room - table seats four comfortably, great for family dinner together or a fun game night with the kids!brbr Living Room - We provide a BYOL environment AKA Bring Your Own Login. The TV is a smart 42” Roku TV so you’ll be able to login into your favorite streaming services (Netflix, Disney +, Hulu, etc.) no problem. The living room features board games under the TV stand and a cozy sofa. Perfect for a quiet night in with family and friends.brGuest accessbrYou will have access to the entire house and backyard. Please do not enter the stand alone garage.brbrSelf check-in: Any time after 3:00 p.m. Our smart lock uses a 4-digit code to gain entry and your code will be the last four digits of your cell phone number. The code will not expire until your check-out time. This feature is especially convenient for long stays because you won’t have to keep up with a house key.brOther things to notebrWhen you book with us all of the popular door delivery services deliver to our home: Instacart, Grubhub, Doordash, Uber Eats, Postmates.brbrFire Extinguisher is located under the kitchen sink.brbrWe use Ring security system. We have security cameras for the front and back yard.brWifi Speed: 250 Mbps

Comfortable Home | Long Stay Discount Available

Chesapeake, Virginia, United States

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Bath

Sleeps

Exceptional(2)

$232.21

Three large bedrooms and two bathrooms in home with eat in kitchen and separate dining room and living room. Televisions with fire stick in living room and Two bedrooms. Home is in a safe family neighborhood close to interstate. There is a nearby mall, restaurants, movies and the New Rivers Casino all within four miles.

Roomy and Cozy 3-bedroom home in Chesapeake near everything.

Chesapeake, Virginia, United States

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Bath

Sleeps

Exceptional(1)

$415.0

Welcome to The Sparks Home! A new build with a cozy yet modern interior. Perfect for couples or smaller groups! brbr5 min walk to a community pond great for fishingbr20 mins from The Downtown Waterside Districtbr35 mins from Virginia BeachbrbrThe first level is all the main living areas, a fully stocked kitchen for you to cook all of your meals, a dining area, a spacious living room w/ 50in flat-screen TV, a half bath, and access to the backyard. Please enjoy our PS4 gaming system included w/ games, access to Netflix & Disney + accounts, and board games/cards inside the entertainment center.brbrThe second level has the first bedroom w/ a queen-size memory foam mattress, mirror, dresser, and closet. The second bedroom has a full size memory foam mattress with a closet. The second floor has a full bathroom w/ a shower and tub, and full access to the laundry room.brbrWe provide:br-Self-check-in with a keypad door lock.br-Clean towels & linens provided for guestsbr-Thorough cleaning services to make sure our guest's stay is in tip-top shape before and after they are gone.br-WiFi brbrBoard games:br-Telestrations After Darkbr-Marvel gamebr-CardsbrbrGuests have access to the main living areas, guest bedrooms, & bathrooms except for the garage & 1 other bedroom that is unavailable.brbrOther things to notebr-No Smoking, $250 smoking feebr-No Parties, unauthorized parties may result in canceling the reservation & feebr-No Petsbr-No loud music after 10pm, no exceptionsbr-4 people max, extra guests past 12am will be charged $100 per person, per nightbrbrANDbrbr-Minimum $250 smoking fee will apply if any evidence of smoking is found inside or outside the home (tobacco or marijuana).brbrGuests have access to the main living areas, guest bedrooms, & bathrooms except for the garage & 1 other bedroom that is locked.brbrThis stay is for 4 people max, perfect for a relaxing experience or small groups. Thank you for your understanding!

The Sparks Home! Relaxing Space + Lux Kitchen

Chesapeake, Virginia, United States

Bed

Bath

Sleeps

Exceptional(1)

$265.67

Sleeps 4 people (Max 3 or 4 adults)brbr• Indoor pool + whirlpoolbr• Breakfast Buffet (Complimentary) br• Evening Socials: (Complimentary) br• Laptop-friendly spacebr• Wi-Fi (Complimentary)br• Fitness Center: 24-hourbr• Business center: 24-hourbr• Shared barbecue areabr• Parking (Complimentary)br• On-site guest service teambr• On-site washer and dryer (Self-serve)br• On-site dry-cleaning servicebrbr1-bedroom suite in Chesapeake! Close to the Virginia Beach oceanfront, only a 25 minute drive away. Local favorites are The Norfolk Botanical Garden, 155-acre garden located on lovely Lake Whitehurst on foot, by tram or by boat. The NAUTICUS Maritime Center is a multi-tiered museum dedicated to the U.S. Navy and is only five miles from the resort. Virginia Beach business district, General Dynamics, and the US Coast Guard.brbrBedding Configuration:brbr• 1 King bedbr• Sleeper sofabrbrLiving Space:brbr• Air-conditionedbr• Flatscreen TV / DVD player brbrKitchen:brbr• Stovebr• Microwavebr• Dishwasherbr• Refrigeratorbr• Cooking utensilsbr• Dishesbr• Generic coffee makerbrbrBathroom:brbr• 1 Bathroombr• Hairdryerbr• Towelsbr• Complimentary toiletriesbrbrThe pool will be closed until January 31st, 2023.brbrOTHER THINGS TO NOTE:brUpon arrival:brbr• A damage deposit of $50 will be processed as a pre-authorization on your credit card and will be released after your departure provided there is no damage, items missing, or extra cleaning requiredbrbrImportant Notesbrbr• Access to all amenities depends on the current situation and government instructionsbr• Indoor pool + whirlpool: Shared (Public), Heated: Open | 8AM - 10PMbr• The Evening Social is offered Monday-Wednesday from 5:30pm-7:00pm to include a light bites, beer, wine and soft drinks depending on availabilitybr• A light housekeeping service is provided from Monday to Friday and a full cleaning is provided every 7 days-br• A number of these units are available, and each is individually decorated. The images shown are a representation of the unit you will receive. At check-in, you will receive a unit of the same type as shown in this listing, complete with the advertised size and number of rooms, but the actual decor in the unit, view, and furniture layout may differbr• By booking this property in Staybridge Chesapeake Virginia Beach you agree to our house rules, health & safety and cancellation policiesbr• You will receive a copy of an Arrival Information after confirming your reservationbr

Condo

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Chesapeake, Virginia, United States

Bed

Bath

Sleeps

Exceptional(5)

Select Dates for Price