A golf course, a large building complex, and a marina by a river.

Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Chesapeake vacation rentals

Apartment, Balcony | Living area

Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
The price is AED 1,067
AED 2,045 total
includes taxes & fees
1 Jul - 2 Jul
Nyakio Suite
TV

Nyakio Suite - Chesapeake

Nyakio Suite - Chesapeake
Greenbrier
The price is AED 777
AED 1,484 total
includes taxes & fees
28 Jun - 29 Jun
Nyakio Suite - Chesapeake
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is AED 577
AED 761 total
includes taxes & fees
30 Jun - 1 Jul
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Terrace/patio

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

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (48 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is AED 744
AED 1,306 total
includes taxes & fees
29 Jun - 30 Jun
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Indoor pool

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

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is AED 672
AED 883 total
includes taxes & fees
5 Jul - 6 Jul
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3 reviews)
The price is AED 577
AED 748 total
includes taxes & fees
28 Jun - 29 Jun
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
10.0 out of 10, Exceptional, (1 review)
The price is AED 624
AED 824 total
includes taxes & fees
28 Jun - 29 Jun
Studio | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

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!
Chesapeake
8.0 out of 10, Very Good, (4 reviews)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Terrace/patio

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (82 reviews)
"The stay was great. We loved walking around the neighborhood at sunset to see the view over the water. We would definitely stay here again. "
United States
Maddi S.
The price is AED 735
AED 1,475 total
includes taxes & fees
2 Jul - 3 Jul
Comfortable Beach Trailer Home
Dining

Luxurious RV

Luxurious RV
Sandbridge
8.6 out of 10, Excellent, (19 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is AED 735
AED 1,467 total
includes taxes & fees
26 Jul - 27 Jul
Luxurious RV
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (87 reviews)
"Very clean and modern room at a very reasonable price. We will definitely stay there again if we are in that area."
United States
Scott
The price is AED 437
AED 502 total
includes taxes & fees
6 Jul - 7 Jul
stayAPT Suites Suffolk-Chesapeake
House | 2 bedrooms

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
7.4 out of 10, Good, (3 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is AED 706
AED 1,315 total
includes taxes & fees
28 Jun - 29 Jun
Ice Ice Baby Downtown Newport News
On the beach, sun loungers

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Willoughby Spit
8.8 out of 10, Excellent, (78 reviews)
"House was steps from the beach. We brought our small dog and the house was pet friendly. Easy to check in and easy to communicate with owner. Would definitely stay here again. "
United States
Angie V.
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Beach nearby, sun loungers

Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking

Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Northeast Virginia Beach
9.8 out of 10, Exceptional, (264 reviews)
"Clean well taken care of property. Process to rent is easy and the owner was extremely accommodating. Thanks for a great stay"
United States
Kevin P.
The price is AED 1,359
AED 2,571 total
includes taxes & fees
21 Jul - 22 Jul
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Exterior

Brick Home with Fenced Yard and Beautiful Waterfront Views in Norfolk, Virginia

Brick Home with Fenced Yard and Beautiful Waterfront Views in Norfolk, Virginia
Willoughby Spit
Brick Home with Fenced Yard and Beautiful Waterfront Views in Norfolk, Virginia
Beach nearby, sun loungers, beach towels

Cozy Beach Home in Oceanview

Cozy Beach Home in Oceanview
Bayview
9.8 out of 10, Exceptional, (47 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
The price is AED 643
AED 1,451 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Beach Home in Oceanview
Beach towels

Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (289 reviews)
"Great place loved it cozy beach house "
United States
JaLiylah M.
The price is AED 856
AED 1,819 total
includes taxes & fees
13 Jul - 14 Jul
Norfolk Beach Cottage Rental
Smart TV, DVD player

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.6 out of 10, Exceptional, (22 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is AED 430
AED 1,236 total
includes taxes & fees
30 Jun - 1 Jul
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Exterior

Coastal Home with Dock, Pier and Waterfront Views in Norfolk, Virginia

Coastal Home with Dock, Pier and Waterfront Views in Norfolk, Virginia
Willoughby Spit
Coastal Home with Dock, Pier and Waterfront Views in Norfolk, Virginia
Living area

Cozy 1-bedroom apartment in beautiful Virginia Beach with AC

Cozy 1-bedroom apartment in beautiful Virginia Beach with AC
Northeast Virginia Beach
The price is AED 826
AED 1,338 total
includes taxes & fees
1 Jul - 2 Jul
Cozy 1-bedroom apartment in beautiful Virginia Beach with AC
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.
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Top Chesapeake Hotel Reviews

Hampton Inn Virginia Beach-Oceanfront South

Hampton Inn Virginia Beach-Oceanfront South

10/10 Excellent
"The room was clean and the view was spectacular. The breakfast was on point."
Andrea 1-night trip
Posted less than an hour ago
Hampton Inn Virginia Beach-Oceanfront South

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Riverwalk Parkway Park and Playground, or you can go with a more remote option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Chesapeake. While you're in the area, you can also enjoy the top-notch restaurants and live music.

What are some of the best vacation home rentals in Chesapeake?

Beachfront Bungalow w/ BEST Location in Ocean View!: This vacation home rental outside of Chesapeake is equipped with a selection of games, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals are there in Chesapeake?

Expedia has 38 vacation rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Riverwalk Parkway Park and Playground and Broadmoor Play Area, whereas Chesapeake City Park and Dismal Swamp Canal are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Naval Station Norfolk and Sandbridge Beach.

What’s a vacation rental in Chesapeake like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chesapeake. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.