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

Holiday Rentals in Chesapeake City County

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Our top choices for Chesapeake City County holiday rentals

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 €168
includes taxes & fees
12 Jul - 13 Jul
Studio | 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 €332
includes taxes & fees
29 Jul - 30 Jul
3-bedroom home away from home in fabulous Chesapeake, Virginia.
TV

Nyakio Suite - Chesapeake

Nyakio Suite - Chesapeake
Greenbrier
The price is €352
includes taxes & fees
8 Aug - 9 Aug
Nyakio Suite - Chesapeake
Pool

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
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Apartment, Balcony | Living area

Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
The price is €527
includes taxes & fees
15 Jul - 16 Jul
Nyakio Suite
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)
"Impressed with the whole experience. "
United States
Patricia M.
The price is €169
includes taxes & fees
12 Jul - 13 Jul
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is €171
includes taxes & fees
12 Jul - 13 Jul
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
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.
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
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!
Indoor pool

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.
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Terrace/patio

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (83 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.
Comfortable Beach Trailer Home
Dining

Luxurious RV

Luxurious RV
Sandbridge
8.6 out of 10, Excellent, (20 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is €350
includes taxes & fees
19 Jul - 20 Jul
Luxurious RV
Outdoor dining

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
8.4 out of 10, Very good, (6 reviews)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
United States
Pam P.
The price is €275
includes taxes & fees
9 Jul - 10 Jul
Knot Three- Balcony View of ICW- Dog Friendly!
Terrace/patio

Sojourn's Harborage | Pet-Friendly

Sojourn's Harborage | Pet-Friendly
East Ocean View
10.0 out of 10, Exceptional, (1 review)
"Beautiful stay. Pet friendly. Spacious. "
United States
Antonio R.
The price is €309
includes taxes & fees
16 Jul - 17 Jul
Sojourn's Harborage | Pet-Friendly
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 €302
includes taxes & fees
12 Jul - 13 Jul
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Dining

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, (7 reviews)
"Quiet comfortable"
United States
Rebecca K
The price is €237
includes taxes & fees
11 Jul - 12 Jul
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Terrace/patio

Knot One- Balcony View of ICW- Dog Friendly!

Knot One- Balcony View of ICW- Dog Friendly!
Coinjock
9.0 out of 10, Wonderful, (8 reviews)
"Loved watching the yachts in the ICW"
United States
susan
The price is €246
includes taxes & fees
22 Jul - 23 Jul
Knot One- Balcony View of ICW- Dog Friendly!
Dining

Unique Space 10 mins from Beach

Unique Space 10 mins from Beach
Northwest
6.0 out of 10, (6 reviews)
"Clean and quiet."
United States
Gerald B.
The price is €184
includes taxes & fees
13 Jul - 14 Jul
Unique Space 10 mins from Beach
Fridge, microwave, oven, stovetop

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, (28 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 €292
includes taxes & fees
14 Jul - 15 Jul
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Fridge, microwave, stovetop, coffee/tea maker

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 €179
includes taxes & fees
16 Jul - 17 Jul
Guesthouse in ideal location with private entrance
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

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

8/10 Good
"Can’t beat the view and that it is a ways away from the boardwalk so not as many people."
Antonia 2-night trip
Posted 1 hour ago
Wyndham Virginia Beach Oceanfront

Find out more about Chesapeake City County

Holiday Homes in Chesapeake City County

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