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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chesapeake vacation rentals

A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

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 373
AED 513 total
includes taxes & fees
1 Nov - 2 Nov
Great Studio | Pool & Hot Tub. Your Next Vacation
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

2. 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 408
AED 553 total
includes taxes & fees
1 Nov - 2 Nov
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
A living room with a sofa, armchair, coffee table, and fireplace.

3. Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
The price is AED 1,086
AED 2,067 total
includes taxes & fees
4 Oct - 5 Oct
Nyakio Suite
A living room with a sofa, armchair, glass coffee table, fireplace, and a television.

4. Nyakio Suite - Chesapeake

Nyakio Suite - Chesapeake
Greenbrier
Nyakio Suite - Chesapeake
A covered porch with a hanging chair, a small table, and a view of a snowy yard.

5. 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, (56 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is AED 582
AED 1,107 total
includes taxes & fees
7 Oct - 8 Oct
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

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

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
10.0 out of 10, Exceptional, (1 review)
Studio | Free Breakfast. Indoor Pool & Hot Tub
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

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

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is AED 371
AED 511 total
includes taxes & fees
1 Nov - 2 Nov
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

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

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is AED 555
AED 731 total
includes taxes & fees
13 Oct - 14 Oct
Studio | Free Breakfast. Indoor Pool & Hot Tub.
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

9. 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 408
AED 553 total
includes taxes & fees
1 Nov - 2 Nov
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

10. 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 447
AED 604 total
includes taxes & fees
1 Nov - 2 Nov
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

11. 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 966
AED 1,255 total
includes taxes & fees
18 Oct - 19 Oct
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
A living room with a sectional sofa, a round ottoman, a globe on a shelf, and artwork on the walls.

12. Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
Portsmouth
9.2 out of 10, Wonderful, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is AED 477
AED 1,371 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
A modern courtyard with white furniture, a central seating area, and a small lawn.

13. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (107 reviews)
"The front desk staff were friendly, welcoming and helpful. The property and room were very clean and quiet. The bed was comfortable, and the room was spacious with a full kitchen. Location is very convenient to restaurants and shopping. Highly recommend this property!"
United States
Kimberly
The price is AED 437
AED 502 total
includes taxes & fees
12 Oct - 13 Oct
stayAPT Suites Suffolk-Chesapeake
A narrow brick pathway flanked by two houses with siding.

14. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (15 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 721 total
includes taxes & fees
29 Oct - 30 Oct
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

15. 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 1,008 total
includes taxes & fees
20 Oct - 21 Oct
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

16. 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
8.8 out of 10, Excellent, (12 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 523
AED 883 total
includes taxes & fees
2 Oct - 3 Oct
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A glass-top table with two cushioned chairs on a wooden deck, a vase with red flowers, and a brick wall.

17. 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, (55 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
The price is AED 459
AED 1,025 total
includes taxes & fees
5 Oct - 6 Oct
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

18. Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (30 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is AED 367
AED 1,059 total
includes taxes & fees
5 Oct - 6 Oct
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A modern kitchen with white cabinets, a built-in oven, and a dining area with a gray sofa and a table.

19. Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (6 reviews)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
The price is AED 441
AED 1,067 total
includes taxes & fees
3 Oct - 4 Oct
Guesthouse in ideal location with private entrance
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

20. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (23 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is AED 437
AED 510 total
includes taxes & fees
4 Oct - 5 Oct
stayAPT Suites Hampton
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

Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

10/10 Excellent
"Nice and clean property. Indoor and outdoor pools on site. Kids friendly. Also indoor pool and hot tub for adults only in the Oceanaire, next door. Outdoor bar/restaurant on site by boardwalk. Fire pits available. The parking garage is across street and can be busy depending on time of day and season. Overall, had a great experience with stay and staff was nice."
Mouna 2-night trip
Posted 6 hours ago
Hilton Vacation Club Ocean Beach Club Virginia Beach

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Broadmoor Play Area, 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?

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom: This vacation home rental outside of Chesapeake is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Chesapeake?

Expedia has 36 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.