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

Chesapeake City County Holiday Rentals

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Our top choices for Chesapeake City County holiday rentals

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, (49 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is HK$1,498
HK$2,649 total
includes taxes & fees
24 Aug - 25 Aug
3-bedroom home away from home in fabulous Chesapeake, Virginia.
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 HK$1,569
HK$1,984 total
includes taxes & fees
25 Aug - 26 Aug
Great Studio | Pool & Hot Tub. Your Next Vacation
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 HK$1,423
HK$1,871 total
includes taxes & fees
2 Aug - 3 Aug
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
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.
The price is HK$1,576
HK$2,091 total
includes taxes & fees
2 Aug - 3 Aug
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.
The price is HK$2,539
HK$3,299 total
includes taxes & fees
25 Aug - 26 Aug
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, (86 reviews)
"This simple trailer home, converted to a stationary beach cottage, has an excellent location on the south end of the Sandbridge neighborhood of Virginia Beach. It is a short walk to a section of the beach servicing the local neighborhood, where dolphins are frequently seen a short distance from shore, and next to a good local restaurant and bar for relaxing after the beach. It is a good option for those looking to enjoy the Sandbridge beaches in a simple beach home without the expenses of the...
United States
Jason
The price is HK$1,569
HK$3,150 total
includes taxes & fees
4 Aug - 5 Aug
Comfortable Beach Trailer Home
Dining

Luxurious RV

Luxurious RV
Sandbridge
8.4 out of 10, Very good, (22 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is HK$1,569
HK$3,150 total
includes taxes & fees
28 Jul - 29 Jul
Luxurious RV
Property grounds

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (7 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (95 reviews)
"Perfect! Will stay again and will look for this brand in my future travels."
United States
Melissa
The price is HK$933
HK$1,072 total
includes taxes & fees
13 Aug - 14 Aug
stayAPT Suites Suffolk-Chesapeake
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, (24 reviews)
"Quite little cottage. Great for a quick stay."
United States
Debbie M.
The price is HK$918
HK$2,666 total
includes taxes & fees
2 Aug - 3 Aug
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Coffee/tea maker, fridge, microwave, stovetop

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 HK$761
HK$1,742 total
includes taxes & fees
28 Jul - 29 Jul
Guesthouse in ideal location with private entrance
Coffee/tea maker, fridge, microwave, oven

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, (29 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 HK$965
HK$2,432 total
includes taxes & fees
24 Aug - 25 Aug
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Terrace/patio

Sojourn's Harborage Pet-Friendly

Sojourn's Harborage Pet-Friendly
East Ocean View
8.4 out of 10, Very good, (8 reviews)
"Everything was cleaned and very nice."
United States
Tilshon
The price is HK$694
HK$2,322 total
includes taxes & fees
25 Aug - 26 Aug
Sojourn's Harborage Pet-Friendly
Property grounds

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)
"Great place great host"
United States
Fabian B.
The price is HK$980
HK$2,143 total
includes taxes & fees
18 Aug - 19 Aug
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Terrace/patio

Knot One- Balcony View of ICW- Dog Friendly!

Knot One- Balcony View of ICW- Dog Friendly!
Coinjock
9.2 out of 10, Wonderful, (9 reviews)
"Loved watching the yachts in the ICW"
United States
susan
The price is HK$1,033
HK$2,156 total
includes taxes & fees
24 Aug - 25 Aug
Knot One- Balcony View of ICW- Dog Friendly!
Smart TV, fireplace

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
8.4 out of 10, Very good, (9 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 HK$1,176
HK$1,963 total
includes taxes & fees
28 Jul - 29 Jul
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Smart TV

Close Beach Access - 150 Yards to Fishing Pier!

Close Beach Access - 150 Yards to Fishing Pier!
Buckroe Beach
9.8 out of 10, Exceptional, (10 reviews)
"Great location and perfect amenities for our stay!"
United States
Annette C.
Close Beach Access - 150 Yards to Fishing Pier!
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 HK$1,167
HK$2,333 total
includes taxes & fees
24 Aug - 25 Aug
Knot Three- Balcony View of ICW- Dog Friendly!
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

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

10/10 Excellent
"Beach view and accessibility to everything"
Candice L 3-night trip
Posted less than an hour ago
Hilton Virginia Beach Oceanfront