Compare Chesapeake Vacation Rentals

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Chesapeake Rentals

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

2.5 out of 5
Free Cancellation
3.24 mi from city center
$218 nightly
The price is $250 total per night
$250 total
Jul 14 - Jul 15
Total includes taxes and fees
Guests of this condo enjoy features like an indoor pool, a hot tub, and laundry facilities. This smoke-free condo building also has barbecue grills.
stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

2.5 out of 5
5961 Harbour View Blvd, Suffolk, VA
11.46 mi from city center
$119 nightly
The price is $137 total per night
$137 total
Jul 28 - Jul 29
Total includes taxes and fees
Guests staying at stayAPT Suites Suffolk-Chesapeake enjoy free WiFi in public areas, laundry facilities, and barbecue grills. If you drive, take advantage of free parking. This smoke-free aparthotel also has a vending machine.
Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV

Cozy Frog on the Beach! 2-bedroom Efficiency w/ Beach Access, WiFi, Smart TV

12.4 mi from city center
$225 nightly
The price is $262 total per night
$262 total
Jul 20 - Jul 21
Total includes taxes and fees
This vacation home is a smoke-free vacation home.
Kitchen
Pet friendly
Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach

Big Kitchen, Two Masters, Hot Tub, Short Walk from Croatan Beach

17.9 mi from city center
$1,365 nightly
The price is $1,572 total per night
$1,572 total
Jul 24 - Jul 25
Total includes taxes and fees
A water park, a rooftop terrace, and a hot tub are featured at this vacation home. Additional amenities include laundry facilities, a garden, and barbecue grills.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
424 Atlantic Avenue, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
18.04 mi from city center
$195 nightly
The price is $227 total per night
$227 total
Jul 6 - Jul 7
Total includes taxes and fees
Guests staying at The Ocean Key Virginia Beach Resort enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include a business center, an arcade/game room, and free newspapers.
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
315 21st St, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
17.97 mi from city center
$174 nightly
The price is $202 total per night
$202 total
Jul 31 - Aug 1
Total includes taxes and fees
At this aparthotel, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include an arcade/game room, express check-in, and express check-out.
Pool
Kitchen
Angie's Guest Cottage

Angie's Guest Cottage

2 out of 5
302 24th Street, Virginia Beach, VA
18.05 mi from city center
$126 nightly
The price is $147 total per night
$147 total
Jul 7 - Jul 8
Total includes taxes and fees
Guests staying at Angie's Guest Cottage enjoy free WiFi in public areas, laundry facilities, and a picnic area. If you decide to drive, there's free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. This smoke-free apartment building also has a garden.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3 out of 5
2207 Atlantic Avenue, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
18.15 mi from city center
$305 nightly
The price is $352 total per night
$352 total
Jul 20 - Jul 21
Total includes taxes and fees
Guests of Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia have access to an indoor pool, a gym, and a sauna. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Other amenities at this beach aparthotel include free WiFi in public areas, a hot tub, and an arcade/game room.
Four Sails Resort

Four Sails Resort

3.5 out of 5
3301 Atlantic Ave, Virginia Beach, VA
18.24 mi from city center
At Four Sails Resort, guests enjoy an indoor pool, a gym, and a sauna. There's free parking if you drive. The 24-hour front desk has staff always at the ready. Other amenities at this beach condominium resort include free WiFi in public areas, free use of bicycles, and laundry facilities.
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

28.96 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
C9083 Cavallo Dunes. Oceanfront, 3 Bedrooms, Hot Tub, Pets OK, 4x4 Area

C9083 Cavallo Dunes. Oceanfront, 3 Bedrooms, Hot Tub, Pets OK, 4x4 Area

29.65 mi from city center
Guests staying at this vacation home enjoy a water park, a hot tub, and laundry facilities.
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

29.75 mi from city center
Guests staying at this vacation home enjoy access to a water park, an outdoor pool, and a hot tub. Other amenities at this beach vacation home include an arcade/game room, laundry facilities, and barbecue grills.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chesapeake Large Group Rentals

How to Book Vacation Rentals in Chesapeake



🏠 What is the best price for Chesapeake vacation rentals?

Chesapeake vacation rentals range in price, starting at $137 per night.


🏠 What types of vacation rentals in Chesapeake can I rent?

Orbitz offers a wide range of Chesapeake rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Chesapeake condo rentals.


🏠 Is it free to cancel my Chesapeake vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Chesapeake vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Chesapeake. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Chesapeake?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Chesapeake apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Chesapeake?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Chesapeake package deals will get you even more savings.

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