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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chesapeake vacation rentals

Indoor pool

1. 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)
"Impressed with the whole experience. "
United States
Patricia M.
The price is AED 501
AED 660 total
includes taxes & fees
6 Sep - 7 Sep
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

2. Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Chesapeake
9.4 out of 10, Exceptional, (8 reviews)
"The condo is nice, clean and very roomy. We love the stay and very convenient. The hotel provides breakfast it’s great!!"
United States
Linh T.
The price is AED 965
AED 1,261 total
includes taxes & fees
6 Sep - 7 Sep
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Terrace/patio

3. 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, (50 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is AED 638
AED 1,185 total
includes taxes & fees
24 Aug - 25 Aug
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Indoor pool

4. 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 474
AED 629 total
includes taxes & fees
6 Sep - 7 Sep
Studio | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

5. 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 509
AED 669 total
includes taxes & fees
6 Sep - 7 Sep
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

6. 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, (5 reviews)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
The price is AED 575
AED 752 total
includes taxes & fees
6 Sep - 7 Sep
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Indoor pool

7. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is AED 474
AED 629 total
includes taxes & fees
6 Sep - 7 Sep
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

8. Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is AED 474
AED 629 total
includes taxes & fees
6 Sep - 7 Sep
Studio | Free Breakfast. Indoor Pool & Hot Tub.
Pool

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

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
The price is AED 544
AED 710 total
includes taxes & fees
9 Sep - 10 Sep
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Pool

10. King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
The price is AED 509
AED 669 total
includes taxes & fees
6 Sep - 7 Sep
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Terrace/patio

11. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (100 reviews)
"Perfect! Will stay again and will look for this brand in my future travels."
United States
Melissa
The price is AED 437
AED 502 total
includes taxes & fees
2 Sep - 3 Sep
stayAPT Suites Suffolk-Chesapeake
Smart TV, DVD player

12. Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.6 out of 10, Exceptional, (24 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is AED 430
AED 1,219 total
includes taxes & fees
23 Aug - 24 Aug
Comfortable & Private 2 Bedrm Cottage w/ King bed.
House (4 Bedrooms) | Interior

13. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is AED 1,069
AED 2,274 total
includes taxes & fees
10 Sep - 11 Sep
Centrally Located Hampton Roads Home w/ Game Room!
Property grounds

14. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and great price."
United States
Shirley
The price is AED 417
AED 487 total
includes taxes & fees
24 Aug - 25 Aug
stayAPT Suites Hampton
Property grounds

15. Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.0 out of 10, Wonderful, (53 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
The price is AED 459
AED 1,025 total
includes taxes & fees
23 Aug - 24 Aug
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Property grounds

16. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (10 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
The price is AED 331
AED 725 total
includes taxes & fees
31 Aug - 1 Sep
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Dining

17. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (9 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is AED 327
AED 1,021 total
includes taxes & fees
31 Aug - 1 Sep
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Smart TV, video games, table tennis, books

18. Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard

Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
Bayview
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful home that is very close to the ocean with lots of options of things to do. We had a wonderful stay!"
United States
Nate K.
The price is AED 1,633
AED 3,237 total
includes taxes & fees
6 Sep - 7 Sep
Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
Smart TV, fireplace

19. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.6 out of 10, Excellent, (11 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
The price is AED 496
AED 843 total
includes taxes & fees
8 Sep - 9 Sep
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Bungalow, 3 Bedrooms | Beach | On the beach

20. Beach Front On The Bay 3 Bedroom Bungalow

Beach Front On The Bay 3 Bedroom Bungalow
3.0 star property
Cottage Park
10.0 out of 10, Exceptional, (1 review)
"This was excellent for my plans. The location was amazing and the beach access top tier. I would definitely rent this property again!"
United States
Simone
The price is AED 1,561
AED 2,514 total
includes taxes & fees
16 Sep - 17 Sep
Beach Front On The Bay 3 Bedroom Bungalow
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

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

10/10 Excellent
"Room was clean and staff was great other than the housekeepers they were rude. I was half scared to ask for and exchange for clean towels. After the attitude she gave another guest.. the free breakfast though was not Great either. I found a hair in my potatoes one morning. And the next day my son did. In his orange juice... so we spent the end of the stay going out to breakfast. It was insanely busy everymorning anyways..the pool was shut down. For two of the days we were there but never got in it because the water always looked brown... the staff at the main desk was always helpful and nice. The parking garage is nice being attached to the hotel though. But a bit annoying if you want to leave. The room itself was great though. The couch sleeper wasnt terrible either. Other than the breakfast and the pool.. id stay again."
nikki 4-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Chesapeake Arboretum, 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?

Oceanfront Beach Estate / Pool / Hot Tub / Arcade: This vacation home rental outside of Chesapeake is located by the ocean and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with an arcade game room and a hot tub.

How many vacation rentals are there in Chesapeake?

Expedia has 37 vacation rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Broadmoor Play Area and Parkview Play Area, whereas Chesapeake City Park and Oak Grove Lake Park 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.