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$2,873 total
includes taxes & fees
29 Jun - 30 Jun
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Living area

Central Chesapeake Stay Near Mall, Trails & parks

Central Chesapeake Stay Near Mall, Trails & parks
Greenbrier
Central Chesapeake Stay Near Mall, Trails & parks
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$1,404
HK$1,795 total
includes taxes & fees
30 Jun - 1 Jul
Great Studio | Pool & Hot Tub. Your Next Vacation
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!
Iron/ironing board, free WiFi

Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
The price is HK$5,452
HK$8,015 total
includes taxes & fees
11 Jun - 12 Jun
Nyakio Suite
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is HK$1,668
HK$2,189 total
includes taxes & fees
9 Jul - 10 Jul
Studio | Free Breakfast. Indoor Pool & Hot Tub.
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$1,503
HK$1,909 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$1,880
HK$2,459 total
includes taxes & fees
14 Jun - 15 Jun
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.
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$3,147 total
includes taxes & fees
8 Jul - 9 Jul
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$3,146 total
includes taxes & fees
23 Jun - 24 Jun
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 HK$1,119
HK$2,251 total
includes taxes & fees
13 Jun - 14 Jun
Knot Three- Balcony View of ICW- Dog 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 HK$917
HK$2,637 total
includes taxes & fees
10 Jun - 11 Jun
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 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
Private kitchen

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is HK$1,811
HK$3,150 total
includes taxes & fees
18 Jun - 19 Jun
The Speakeasy Downtown Newport News
Property grounds

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
9.2 out of 10, Wonderful, (17 reviews)
"George was a very responsive host. Great beachfront location. Very comfortable relaxing setting. Will definitely be back!!! "
United States
Carter S.
The price is HK$1,587
HK$2,822 total
includes taxes & fees
11 Jun - 12 Jun
Beachfront Bungalow w/ BEST Location in Ocean View!
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
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$990
HK$2,088 total
includes taxes & fees
16 Jun - 17 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$784
HK$2,259 total
includes taxes & fees
15 Jun - 16 Jun
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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
10 Jun - 11 Jun
Private 1 Bed Apt - Historic Olde Towne Portsmouth
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

Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

10/10 Excellent
"We are happy with our stay. Wiston at front desk was following up periodically to see if we need anything which was really amazing service and help. Property is clean, our room was just renovated and it has a nice view and good room services"
Wael 3-night trip
Posted 3 hours ago
Holiday Inn & Suites Virginia Beach North Beach by IHG