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, (47 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is HK$1,677
HK$2,872 total
includes taxes & fees
29 Jun - 30 Jun
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$1,662
HK$2,118 total
includes taxes & fees
7 Jul - 8 Jul
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
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
The price is HK$1,530
HK$1,985 total
includes taxes & fees
29 Jun - 30 Jun
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Living area

Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
The price is HK$4,894
HK$7,374 total
includes taxes & fees
17 Jun - 18 Jun
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 HK$1,383
HK$1,789 total
includes taxes & fees
30 Jun - 1 Jul
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$1,481
HK$1,947 total
includes taxes & fees
30 Jun - 1 Jul
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$1,742
HK$2,274 total
includes taxes & fees
30 Jun - 1 Jul
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
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$1,513
HK$1,984 total
includes taxes & fees
29 Jun - 30 Jun
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Terrace/patio

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (80 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.
The price is HK$1,567
HK$3,129 total
includes taxes & fees
28 Jun - 29 Jun
Comfortable Beach Trailer Home
Dining

Luxurious RV

Luxurious RV
Sandbridge
8.4 out of 10, Very good, (18 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is HK$1,567
HK$3,129 total
includes taxes & fees
16 Jun - 17 Jun
Luxurious RV
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.4 out of 10, Exceptional, (82 reviews)
"Very clean and modern room at a very reasonable price. We will definitely stay there again if we are in that area."
United States
Scott
The price is HK$933
HK$1,071 total
includes taxes & fees
29 Jun - 30 Jun
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, (22 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is HK$917
HK$2,637 total
includes taxes & fees
14 Jun - 15 Jun
Comfortable & Private 2 Bedrm Cottage w/ King bed.
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$1,144
HK$2,289 total
includes taxes & fees
16 Jun - 17 Jun
Knot Three- Balcony View of ICW- Dog Friendly!
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 HK$972
HK$2,006 total
includes taxes & fees
14 Jun - 15 Jun
Knot One- Balcony View of ICW- Dog Friendly!
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 HK$807
HK$2,294 total
includes taxes & fees
17 Jun - 18 Jun
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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
9.6 out of 10, Exceptional, (4 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 HK$628
HK$2,079 total
includes taxes & fees
16 Jun - 17 Jun
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
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
9.4 out of 10, Exceptional, (6 reviews)
"It’s was great staying "
United States
Shalena K.
The price is HK$1,175
HK$1,952 total
includes taxes & fees
15 Jun - 16 Jun
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Terrace/patio

Sojourn's Harborage Pet-Friendly

Sojourn's Harborage Pet-Friendly
East Ocean View
9.2 out of 10, Wonderful, (7 reviews)
"Everything was cleaned and very nice."
United States
Tilshon
The price is HK$1,033
HK$2,741 total
includes taxes & fees
13 Jul - 14 Jul
Sojourn's Harborage Pet-Friendly
Shower, bidet

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (5 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is HK$635
HK$1,456 total
includes taxes & fees
25 Jun - 26 Jun
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Beach nearby, sun-loungers, beach towels

Cozy Beach Home in Oceanview

Cozy Beach Home in Oceanview
Bayview
9.8 out of 10, Exceptional, (46 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
The price is HK$1,371
HK$3,097 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Beach Home in Oceanview
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

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

10/10 Excellent
"We really enjoyed our stay!"
Miles 1-night trip
Posted 6 hours ago
Hyatt Place Virginia Beach / Oceanfront