Chesapeake Vacation Rentals, Hotels, & Places to Stay
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Luxury Places to Stay in Chesapeake
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Top-Rated Vacation Rentals with a Pool in Chesapeake
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Pet-Friendly Vacation Rentals in Chesapeake
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Large Vacation Homes & Villas in Chesapeake
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Wheelchair Accessible Vacation Homes in Chesapeake
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Chesapeake Varoom and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Chesapeake
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Book a Last Minute Place to Stay in Chesapeake
About Chesapeake Vacation Rentals
There are more than 175 places to stay that are available in Chesapeake. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Chesapeake.
Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in Chesapeake, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Chesapeake. Places to stay near Chesapeake are 445.15 ft² on average, with prices averaging US $184 a night.
Varoom helps you discover places to stay and suggests things to do to create great travel memories in Chesapeake. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Top Rental Accommodation Types in Chesapeake
| Type | Count |
|---|---|
| Vacation Homes | 63 |
| Holiday Apartments | 20 |
| Cottages | 2 |
Use these Quick Filters to Find a Vacation Rental in Chesapeake
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★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Chesapeake today.
Weather in Chesapeake, VA
View the weather forecast for Chesapeake before booking your Chesapeake Vacation Rentals to confirm your best time to go.
Top Attractions Around Chesapeake, VA
Varoom offers a large selection of top attractions around Chesapeake . Research things to do on your vacation before you visit Chesapeake.
Other Places to Stay in Chesapeake, VA
Complexes around Chesapeake, VA
Frequently Asked Questions About Chesapeake?
What are the top vacation rentals in Chesapeake?
We have scoured the web to find you options in Chesapeake. If you plan on staying near or in the Chesapeake area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the Top Places to Stay in Chesapeake:
- Fully renovated and Modernized home in Chesapeake
- Bright Chesapeake Home Near Shopping & Dining
- The Sparks Home! Relaxing Space + Lux Kitchen
- Beautiful home in Chesapeake
- Great Studio | Pool & Hot Tub. Your Next Vacation
- Looking for 30 days or more contact me via VRBO for special pricing. Hot Tub
- The Full House
- Five Star Stay - Downtown 1BR/1BA
- King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
- NEWLY REMODELED 2 BEDROOM DUPLEX
How many vacation rentals have private pools in Chesapeake?
We have found 7 places to stay that feature a private swimming pool in or near Chesapeake. Some of the best places to stay that feature or have access to a swimming pool are:
- Hampton Inn & Suites Chesapeake-Battlefield Boulevard
- Staybridge Suites Chesapeake-Virginia Beach by IHG
- Comfort Inn & Suites Chesapeake - Portsmouth
- SpringHill Suites Chesapeake Greenbrier
Which vacation homes in Chesapeake are best for families?
If you are looking for a place to stay that is family-friendly in Chesapeake, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Chesapeake:
- Convenient to all 7 cities
- Shop, Golf and Explore Family Home in Chesapeake!
- WoodSpring Suites Chesapeake - Norfolk South
How many Varoom vacation rentals are available in Chesapeake?
Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2025 is over 175 in the Chesapeake area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Chesapeake.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Greenbrier East Vacation Rentals in Chesapeake, Virginia | 26 |
| Western Branch North Vacation Rentals in Chesapeake, Virginia | 70 |
| Greenbrier West Vacation Rentals in Chesapeake, Virginia | 60 |
| Great Bridge Vacation Rentals in Chesapeake, Virginia | 103 |
| Deep Creek South Vacation Rentals in Chesapeake, Virginia | 145 |
| Churchland Vacation Rentals in Chesapeake, Virginia | 63 |
| Great Bridge East Vacation Rentals in Chesapeake, Virginia | 27 |