Home Vacation Rentals By Owner In Chesapeake, VA

Showing 53 Of 53 Vacation Rentals
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Exceptional(24)

$192.9

/ Nightly
Private Vacation Home

Country Escape Home in the Woods- Chesapeake, VA

Chesapeake, Virginia, United States

Escape your day to day life to come enjoy this house in the country. This is a great house for you, your family and friends. It has 3 bedrooms, living room, den, full kitchen, dining room, laundry room and a bathroom. It also boasts a large covered deck with a propane fire-pit and dining area so you can enjoy the great outdoors and watch the stars at night. This is a great rental to be away from the city life yet close to a lot of destinations. This house is within 1.5 miles to Ballahack Airsoft Field, Triple R Ranch, Northwest Naval Annex and Navy Exchange open to the public and a couple miles further is the Great Dismal Swamp, Bobs Fishing Hole/Boat Ramp, NC State Line and many more great places.brbrThis home has 3 bedrooms, living room, den (with small work area), full kitchen, dining room, laundry room and a bathroom. It also boasts a large covered deck with a propane fire-pit and dining area so you can enjoy the great outdoors and watch the stars at night. brBedroom #1- Queen Bed, Recliner, TV, Closet, DresserbrBedroom #2- Twin Bunkbeds, TV, 2 Dressers, ArmoirebrBedroom #3- Queen Bed, TV, Closet, Dresser brFront Living Room- Couch, Chair, TV, 2 TV Dinner tablesbrDining Room- Table for 6, Coffee Bar brDen- Two Couches, TV, Small Desk, Desk Chair, PrinterbrKitchen- Fridge, Stove/oven, Microwave, Dishwasher, Kuerig and regular Coffee Maker, Toaster, Can Opener, Dishes for 6-9, Pots and PansbrLaundry/Mud Room, New washer and dryerbrFront Porch- Sitting Area brBack Covered Porch- Propane Fire Table, Dining Table, New Grill, Cafe LightsbrbrBackyard - Huge Yard, Picnic Area (4 picnic tables) with cafe lights, Playground, Sand Play Area with toys (Note: this is a common area with garage rental)brbrGuest Access: The house, backyard and picnic area is included in this rental. The garage and garage apartment is not part of the rental. brbrSecurity: There are 3 security cameras outside- one on the front porch facing driveway, two on the back porch railing facing the garage. brThis home is in the middle of some great design improvements in between rentals so keep checking back to see the new photos! You will LOVE this country home in the woods!!brbrCheck out our Facebook page to see all our great reviews and guest photos: https://www.facebook.com/countryescaperental This unique rental is in the country in the middle of farmland and woods so if you don’t like bugs, critters etc this isn’t the rental for you. Depending on the weather and time of year, you may see some deer, wild turkey, lady bugs, mosquitoes, carpenter bees, lizards, water bugs, field mice etc. While we pay for routine and proactive pest control every blue moon there may be a sighting.
Bed 3

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Bath 1

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Sleep 6

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$417.73

/ Nightly
Private Vacation Home

Charming 3-bedroom bungalow with WiFi, AC in Chesapeake

Chesapeake, Virginia, United States

Nestled in Chesapeake, this delightful bungalow offers 3 cozy bedrooms - 2 with queen beds and 1 with a twin bed. With amenities like a hair dryer, AC, and WiFi, guests can relax and unwind in this peaceful retreat. Whether you're exploring the area or simply enjoying a quiet evening in, this gorgeous property is the perfect home away from home. We look forward to hosting you at our place.
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Bath 2

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Sleep 5

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$126.2

/ Nightly
Apartment

First Class Lvng - 2BR, 2BA, cool/cozy

Chesapeake, Virginia, United States

Welcome to this stylish two-bedroom, two-bath apartment in Chesapeake, VA, perfect for executive trips. Located just off RTE 664, it provides quick access to local hospitals, military bases, downtown Norfolk (15 min), and the nearest hospital (6 min). Relax in the minimalistic ambiance, featuring two comfortable beds. This is a top floor unit (3rd flr), no elevators. Enjoy nearby water bodies and beaches. With advanced notice, we`re here to ensure a delightful stay for busy professionals.
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Bath 2

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Sleep 4

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$305.31

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Condo

Cozy 2-bedroom condo in wonderful Chesapeake with fitness room, WiFi

Chesapeake, Virginia, United States

Welcome to this lovely condo in Chesapeake. This enjoyable property features 2 cozy bedrooms, a fitness room, WiFi, and all the essentials for a comfortable stay. The beautiful decor and convenient amenities make it a perfect retreat for guests looking to relax and unwind. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out.
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Bath 1

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Sleep 6

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Exceptional(3)

$230.28

/ Nightly
Apartment

Great Studio | Pool & Hot Tub. Your Next Vacation

Chesapeake, Virginia, United States

This studio queen condo in Chesapeake, Virginia Beach is an excellent choice for families or friends. This is your perfect home away from home.brbr• FREE Wi-Fibr• FREE Parkingbr• Laptop-friendlybrbrEnjoy a wonderful trip to Chesapeake, courtesy of our Studio Suite! Sleeps up to 2 people. Our condo features: brbr• 1 Queen Bedbr• Air-conditioned living spacebr• Cable television and DVD playerbr• Kitchen: Stove, Microwave Oven, Toaster, Refrigerator (Full), Icemaker In Refrigerator, Dishwasher, Pots/Pans/Serving Dishes, Plates/Glassware, Silverware, Dining Tablebr• Bathroom: Hairdryer, towels, and complimentary toiletries.brbrAdditional amenities you’ll find at Staybridge Chesapeake Virginia Beach include:brbr• Seasonal Indoor Pool and Hot Tubbr• 24-hrs Fitness and Business center br• On-site Guest Self-Laundry, Same-Day Dry Cleaningbr• Shared BBQ areabrbrLOCAL FAVORITESbrbrOutdoor Activities:brbr• Chesapeake City Park: Pine forest featuring open space for dog & skate parks plus an expansive playground & horseshoesbr• City View Park: Various playgrounds, basketball courts, baseball fields & picnic areas fill this lively green spacebrbrLocal Dining:brbr• Cracker Barrel Old Country Store: Homey chain restaurant serving American comfort food, with an on-site general storebr• Olive Garden Italian Restaurant: Lively, family-friendly chain featuring Italian standards such as pastas & saladsbr• Smokey Bones Chesapeake: Smokehouse & barbecue dishes fill out the menu of this easygoing bar & grill chainbr• Abuelo's Mexican Restaurant: Texas-based chain restaurant serving Mexican food & margaritas in a hacienda-style settingbr• Rancho Grande Mexican Restaurant:brbrPlaces to See:brbr• Oak Grove Lake Parkbr• Fun Forestbr• Providence ParkbrbrThe pool will be closed until January 31st, 2023.brbrOTHER THINGS TO NOTE:br• The indoor pool is open from 8am to 10pmbr• Complimentary parking is available on-sitebr• 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 required.br• A light housekeeping service is provided from Monday to Friday and a full cleaning is provided every 7 daysbr• 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 differ. You will have access to all amenities advertised!br• 24/7 Customer Supportbr
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Exceptional(21)

$358.5

/ Nightly
Private Vacation Home

Fully renovated and Modernized home in Chesapeake

Chesapeake, Virginia, United States

Book today and you will not be disappointed! Everything in home has been updated. New flooring and carpet throughout house. Home includes top notch appliances and furniture. Property is in a great location. 5-10 minutes away from Greenbrier mall, shopping plazas and great restaurants. 15 minutes away from Virginia Beach Ocean front/strip and 10 minutes from Ocean View in Norfolk. Approximately 15 minutes away from Rivers Casino in Portsmouth. Enjoy your next stay at this modernized home!
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Exceptional(1)

$790.83

/ Nightly
Private Vacation Home

Perfect Getaway in Chesapeake

Chesapeake, Virginia, United States

Please don’t instantly book. Located in Chesapeake, enjoy what this 3-bedroom house has to offer. This beautiful property features 1 king bed and 2 queen beds, along with 3 bathrooms equipped with a shower, jetted bathtub, and hair dryer. With additional office spaces that include futon beds, guests can comfortably work or relax. We're happy to assist with any questions while you stay at our house. Enjoy the open backyard with a nice pool and patio for you and your family and friends.
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Bath 3

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Sleep 10

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Exceptional(5)

$429.42

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Private Vacation Home

Welcome to our cozy home in Chesapeake

Chesapeake, Virginia, United States

Welcome to our wonderful home located in a very desirable area in Chesapeake Virginia. Our home is a 3 bedroom 3 bath that has a lovely decorated loft and a finish attic over the garage.brIts located 5 min from Greenbriar Mall, 20 minutes from all major military bases and 20 minutes from Virginia Beach Oceanfront.brIt has an eat-in kitchen with desirable appliances. It comes with washer and dryer for all your daily family needs. Its located in a quiet family oriented community in the heart of Chesapeake Virginia.
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Bath 3

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Exceptional(22)

$325.92

/ Nightly
Private Vacation Home

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

Chesapeake, Virginia, United States

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.
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Sleep 5

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Exceptional(18)

$224.38

/ Nightly
Private Vacation Home

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

Chesapeake, Virginia, United States

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.
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$150.35

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Apart-hotel

YourSpace Hotels Chesapeake-Modern Extended Stay Suites with Kitchens

Chesapeake, Virginia, United States

At YourSpace Hotels Chesapeake, a stay is designed to feel more comfortable, more functional, and more relaxed than a traditional hotel visit. From the moment guests arrive, they are welcomed into a modern extended-stay property built for the way people really travel today—whether that means a short project assignment, temporary relocation, business travel, government travel, family transition, or simply needing a place that works better for a longer visit.brbrThe experience begins with a clean, newly built hotel environment and a 24-hour front desk team ready to assist at any time of day or night. Check-in is completed at the front desk, making arrival simple and direct. Once checked in, guests can settle into a suite designed to support both comfort and routine. Rather than a standard hotel room with limited space, guests can expect a more thoughtful layout that gives them room to sleep, relax, work, and stay organized.brbrEach suite is designed to help guests feel at home. Comfortable beds, free Wi-Fi, dedicated workspace, convenient storage, and a 55-inch TV create a setting that works for both rest and productivity. Many guests will appreciate having a separate area to unwind, whether that means watching a show after work, enjoying a quiet evening, answering emails, or simply stretching out with more space than a traditional overnight room typically offers. Select living areas also include a sofa bed, giving added flexibility for travel needs.brbrOne of the biggest advantages of staying at YourSpace Hotels Chesapeake is the in-suite kitchen. Guests can store groceries, prepare meals on their own schedule, and enjoy the convenience of having a kitchen right in their room. For travelers staying more than a night or two, this makes a major difference in both comfort and routine. Instead of depending on takeout or restaurant meals for every meal, guests have the option to keep things simple and familiar, whether making breakfast before work, preparing dinner in the evening, or storing snacks and drinks for later.brbrAnother feature that helps shape the stay is the in-suite washer and dryer. For extended-stay guests, this can make daily life far easier. Laundry can be done in the privacy of the suite and on the guest’s own schedule, without the inconvenience of leaving the room or searching for off-site options. Whether someone is staying for work, travel, relocation, or an unexpected life event, having this level of convenience can make a stay feel smoother and less disruptive.brbrBeyond the suite itself, the property offers shared spaces and amenities designed to support everyday needs. Guests can stop by the Market Pantry for convenient grab-and-go items and everyday essentials, making it easy to pick up refreshments or a quick snack at any time. The fitness space gives guests a place to maintain their routine while away from home, and the outdoor grilling area with patio furniture offers an inviting place to cook, gather, or simply enjoy time outside. For guests traveling with pets, pet-friendly accommodations and a dedicated pet run area help make the stay more convenient and enjoyable for both guest and companion.brbrThe hotel also offers practical extras that support a longer stay experience. EV charging is available on-site for guests traveling by electric vehicle. Paid lockers provide secure personal storage for those who may need extra space during their stay. A small appliance guest share program adds another layer of flexibility by making additional kitchen-related conveniences available to guests during their visit. These details are part of what helps the property feel designed for real life, not just overnight lodging.brbrGuests can also expect a calm and welcoming atmosphere throughout the hotel. Quiet hours are observed each evening to help create a more peaceful environment for rest and relaxation. This is especially important for travelers staying multiple nights, guests working early hours, professionals on assignment, and anyone looking for a stay that feels more settled and less hectic. The goal is to provide a space where guests can recharge comfortably at the end of the day.brbrSafety and peace of mind are also part of the guest experience. Exterior security cameras monitor public outdoor areas such as entrances, parking areas, and the building perimeter. These cameras are in place to support guest and property security while respecting privacy, with no cameras located inside guest suites or private interior spaces.brbrLocation is another part of what makes a stay here convenient. YourSpace Hotels Chesapeake offers access to Chesapeake, Suffolk, Norfolk, and the surrounding Hampton Roads area, making it a practical option for business travelers, government travelers, project-based workers, relocating families, and guests visiting the region for a variety of reasons. Its location supports both local mobility and everyday convenience while giving guests a modern place to return to at the end of the day.brbrA stay at YourSpace Hotels Chesapeake is ideal for guests who want more than a standard hotel room. It is designed for people who value having space to live, work, cook, do laundry, stay connected, and maintain their routines while away from home. Whether the stay is for a few nights, a few weeks, or longer, the experience is intended to feel easy, useful, and comfortable from start to finish.brbrGuests who book can expect a modern extended-stay hotel experience with the features that matter most: a clean and newly built environment, comfortable suites, practical amenities, pet-friendly options, free Wi-Fi, thoughtful shared spaces, and a team available around the clock to help support the stay. At YourSpace Hotels Chesapeake, the experience is centered on helping guests settle in, stay comfortably, and enjoy a space that works for the way they travel.
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Exceptional(2)

$303.89

/ Nightly
Private Vacation Home

Shop, Golf & Explore: Family Home in Chesapeake!

Chesapeake, Virginia, United States

Easy Hwy Access | BBQ Ready | Close to Community Lake & Golf CoursebrbrGet ready for good times and relaxation! This 3-bedroom, 2-bath vacation rental is situated in a peaceful neighborhood and features a fenced yard, a full kitchen, and a prime location, making it ideal for family fun or a group trip. Peruse the shops at the Greenbrier Mall, visit the Norfolk Botanical Garden, or stroll along Virginia Beach before returning home to unwind on the patio or stream your favorites on the Smart TV.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 full bedbr- Bedroom 3: 2 full bedsbrbrKITCHENbr- Stove/oven, refrigerator, microwave, dishwasherbr- Drip coffee maker, rice cookerbr- Cooking basics, dishware & flatwarebr- Trash bags/paper towelsbrbrMAIN FEATURESbr- Smart TVbr- Dining tablebr- Chandeliersbr- Private patiobr- Gas grill (propane provided)brbrGENERALbr- Central heating & A/Cbr- Washer/dryer, laundry detergentbr- Linens/towels, iron/boardbr- Complimentary toiletries, hair dryerbr- Free WiFibrbrFAQbr- 3 exterior security cameras (facing out)br- Fireplace (decorative only)brbrACCESSIBILITYbr- Single-story home, 1 step to accessbr- Grab rails in bathroombrbrPARKINGbr- Driveway (2 vehicles)brbr-- THE LOCATION --brbr- Easy access to I-64br- 0.8 miles to Greenbrier Mall & Greenbrier Country Clubbr- 3 miles to Chesapeake Regional Medical Centerbr- 8 miles to Town Point Parkbr- 14 miles to Norfolk Botanical Gardenbr- 19 miles to Virginia Beach Oceanfrontbr- 13 miles to Norfolk Int'l Airportbrbr-- 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- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 1 step to accessbr- The fireplace is not available for guest usebr- Your safety matters. This property features 3 exterior security cameras: 1 camera is located on the roof facing the driveway, 1 camera is located at the front door facing the front outdoor entryway, and 1 camera is located on the roof facing the fence. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound continuously
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$784.0

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Private Vacation Home

Ultimate Vacation Home

Chesapeake, Virginia, United States

Welcome to this stunning modern vacation home, where sleek design meets ultimate comfort. Step outside onto the expansive patio, where your private oasis awaits. The centerpiece of the outdoor space is a sparkling swimming pool, perfect for cooling off on warm summer days or taking a refreshing dip under the stars. Lounge chairs and patio furniture are poolside, providing the ideal spot for soaking up the sun or enjoying alfresco dining with family and friends.brbrHome sleeps : 5brBedroom 1 (1 King, 1 Futons)brBedroom 2 (1 Queen)brBedroom 3 (1 Queen)br1 Air MattressbrbrBouncy House is available upon request before arrival. For a flat rate of $250, you will have it for your stay.brbrGreenbrier Mall 6 minsbrGrocery Stores 5 minsbrVA Beach 22 minsbrRivers Casino Portsmouth 22 minsbrOver 50 restaurants within 5 mins of the propertybrApex Entertainment 16 minsbrNorfolk 18 minsbrHampton 30 minsbrNewport News 35 mins
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Home Most popular vacation rentals in Chesapeake

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$790.83

/ Nightly
Private vacation home

Perfect Getaway in Chesapeake

Chesapeake, Virginia, United States

Bed 3

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Bath 3

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$134.23

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Private vacation home

NEWLY REMODELED 2 BEDROOM DUPLEX

Chesapeake, Virginia, United States

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$156.68

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Guest house

Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees

Chesapeake, Virginia, United States

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$192.90

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Private vacation home

Country Escape Home in the Woods- Chesapeake, VA

Chesapeake, Virginia, United States

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Sleep 6

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$213.85

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Private vacation home

The Full House

Chesapeake, Virginia, United States

Bed 3

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Bath 2

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Sleep 5

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$230.28

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Apartment

Great Studio | Pool & Hot Tub. Your Next Vacation

Chesapeake, Virginia, United States

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Sleep 2

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$358.50

/ Nightly
Private vacation home

Fully renovated and Modernized home in Chesapeake

Chesapeake, Virginia, United States

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Bath 2

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Sleep 8

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$533.85

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Private vacation home

Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home

Chesapeake, Virginia, United States

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Bath 2

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Sleep 8

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$409.52

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Private vacation home

The Sparks Home! Relaxing Space + Lux Kitchen

Chesapeake, Virginia, United States

Bed 2

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Bath 1

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Sleep 4

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$314.14

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Private vacation home

Looking for 30 days or more contact me via VRBO for special pricing. Hot Tub

Chesapeake, Virginia, United States

Bed 4

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Bath 2

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Sleep 7

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