A large building with a prominent arched entrance and a green roof.

Vacation Rentals in Chesapeake City County

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Our top choices for Chesapeake City County vacation rentals

A residential building with a stone facade, a yellow door, and a covered porch area.

1. 4BR Townhome in Riverfront Chesapeake Community

4BR Townhome in Riverfront Chesapeake Community
3.0 star property
Deep Creek South
4BR Townhome in Riverfront Chesapeake Community
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

2. 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 ￥20,632
￥27,335 total
includes taxes & fees
Nov 1 - Nov 2
Great Studio | Pool & Hot Tub. Your Next Vacation
A covered porch with a hanging chair, a small table, and a view of a snowy yard.

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, (56 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is ￥24,142
￥45,938 total
includes taxes & fees
Nov 4 - Nov 5
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.

4. 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 ￥22,310
￥29,444 total
includes taxes & fees
Nov 8 - Nov 9
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
A modern kitchen with dark wooden cabinets, stainless steel appliances, a granite countertop, and a bar stool.

5. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
The price is ￥23,374
￥98,813 total
includes taxes & fees
Nov 9 - Nov 10
Entire Home in Chesapeake, Virginia
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

6. 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 ￥42,438
￥55,119 total
includes taxes & fees
Nov 15 - Nov 16
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

7. 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 ￥25,496
￥33,650 total
includes taxes & fees
Nov 25 - Nov 26
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

8. 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 ￥24,826
￥32,339 total
includes taxes & fees
Nov 8 - Nov 9
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

9. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
2.0 star property
Chesapeake
The price is ￥30,590
￥101,699 total
includes taxes & fees
Nov 12 - Nov 13
Entire Home in Chesapeake, Virginia
An outdoor seating area with wicker furniture and orange Adirondack chairs.

10. Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1,450 reviews)
"Great stay"
United States
Nancy
The price is ￥18,869
￥31,032 total
includes taxes & fees
Nov 14 - Nov 15
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
A modern courtyard with white furniture, a central seating area, and a small lawn.

11. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (113 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
The price is ￥18,668
￥21,439 total
includes taxes & fees
Nov 9 - Nov 10
stayAPT Suites Suffolk-Chesapeake
An indoor swimming pool with clear glass ceilings, lounge chairs, and a view of the outside.

12. The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort
3.0 star property
Northeast Virginia Beach
7.6 out of 10, Good, (1,687 reviews)
"The room was nice and spacious. The hot tub wasn't working. Overall a great place to stay."
United States
Sharon
The price is ￥14,112
￥16,599 total
includes taxes & fees
Nov 1 - Nov 2
The Ocean Key Virginia Beach Resort
Living area

13. 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 ￥16,942
￥54,050 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
A two-story house with a white porch, a red door, and a small Christmas tree.

14. Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.4 out of 10, Very good, (250 reviews)
"Not a top of the line hotel, but it was clean, good location, and it served our needs. We would definitely stay here again."
United States
Cheryl
The price is ￥12,424
￥16,136 total
includes taxes & fees
Oct 26 - Oct 27
Angie's Guest Cottage
A gym with a bench, dumbbells, and a yoga mat.

15. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.0 out of 10, Wonderful, (32 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is ￥15,121
￥17,703 total
includes taxes & fees
Oct 26 - Oct 27
stayAPT Suites Hampton
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

16. 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)
"This was the perfect experience for our vacation and we highly recommend this property and the host was so easy to get in contact with!"
United States
Coachmeech Gaming O.
The price is ￥12,565
￥41,258 total
includes taxes & fees
Nov 1 - Nov 2
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.

17. 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, (13 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 ￥22,354
￥37,726 total
includes taxes & fees
Nov 4 - Nov 5
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A narrow brick pathway flanked by two houses with siding.

18. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (17 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 ￥12,706
￥29,626 total
includes taxes & fees
Oct 29 - Oct 30
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

19. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Great property not too far from the beaches! Between the pool, hot tub, mini golf, and theater room, our family had plenty to do at the house when we weren't out exploring Virginia Beach. Owner was quick to respond to any questions or needs as well."
United States
Erin W.
The price is ￥40,802
￥96,100 total
includes taxes & fees
Oct 26 - Oct 27
Wooded Wonderland
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

20. 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, (32 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 ￥16,942
￥46,834 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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 City County Hotel Reviews

Boardwalk Resort and Villas

Boardwalk Resort and Villas

10/10 Excellent
"It was great, only thing I don't like is the garage in the parking is awful. And having breakfast available at the hotel would be fantastic!"
Becky 1-night trip
Posted 8 hours ago
Boardwalk Resort and Villas

Find out more about Chesapeake City County

Vacation Apartments in Chesapeake City County

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