Chesapeake City County Holiday Rentals

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Our top choices for Chesapeake City County holiday rentals

Indoor pool

Apartment in Chesapeake

Great Studio | Pool & Hot Tub. Your Next Vacation
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
The price is HK$954
HK$1,277 total
includes taxes & fees
15 Mar - 16 Mar
Great Studio | Pool & Hot Tub. Your Next Vacation
Terrace/patio

Holiday Home in Chesapeake

3-bedroom home away from home in fabulous Chesapeake, Virginia.
10.0 out of 10, Exceptional, (43 reviews)
"This was a wonderful place that was perfect for girls trip! I would definitely recommend and stay again!!"
United States
Tabitha P.
The price is HK$1,377
HK$2,408 total
includes taxes & fees
31 Mar - 1 Apr
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Indoor pool

Condo in Chesapeake

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is HK$1,184
HK$1,541 total
includes taxes & fees
5 Apr - 6 Apr
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

Apartment in Chesapeake

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
The price is HK$903
HK$1,219 total
includes taxes & fees
15 Mar - 16 Mar
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

Apartment in Chesapeake

Studio | Free Breakfast. Indoor Pool & Hot Tub
The price is HK$1,087
HK$1,437 total
includes taxes & fees
15 Mar - 16 Mar
Studio | Free Breakfast. Indoor Pool & Hot Tub
Pool

Condo in Chesapeake

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
The price is HK$1,221
HK$1,584 total
includes taxes & fees
15 Mar - 16 Mar
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

Condo in Chesapeake

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
8.0 out of 10, Very good, (4 reviews)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
The price is HK$1,243
HK$1,609 total
includes taxes & fees
5 Apr - 6 Apr
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Indoor pool

Apartment in Chesapeake

Studio | Free Breakfast. Indoor Pool & Hot Tub.
The price is HK$1,294
HK$1,668 total
includes taxes & fees
5 Apr - 6 Apr
Studio | Free Breakfast. Indoor Pool & Hot Tub.
Pool

Condo in Chesapeake

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
The price is HK$1,330
HK$1,709 total
includes taxes & fees
2 Apr - 3 Apr
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
TV

Holiday Home in Northeast Virginia Beach

The Art Door Duplex only minutes from beach
9.6 out of 10, Exceptional, (108 reviews)
"The rooms were very clean and be was comfortable!"
United States
CYMANDYE V.
The price is HK$781
HK$1,795 total
includes taxes & fees
12 Mar - 13 Mar
The Art Door Duplex only minutes from beach
Outdoor dining

Holiday Home in Coinjock

Knot Three- Balcony View of ICW- Dog Friendly!
9.6 out of 10, Exceptional, (5 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$842
HK$1,892 total
includes taxes & fees
17 Mar - 18 Mar
Knot Three- Balcony View of ICW- Dog Friendly!
Fridge, microwave, oven, stovetop

Holiday Home in Portsmouth

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
9.2 out of 10, Wonderful, (26 reviews)
"The place was noce and quiet. "
United States
Tomar B.
The price is HK$782
HK$2,218 total
includes taxes & fees
17 Mar - 18 Mar
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Dining

Holiday Home in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in 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$627
HK$2,012 total
includes taxes & fees
21 Mar - 22 Mar
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Terrace/patio

Apartment in Coinjock

Knot One- Balcony View of ICW- Dog Friendly!
9.0 out of 10, Wonderful, (8 reviews)
"Loved watching the yachts in the ICW"
United States
susan
The price is HK$737
HK$1,756 total
includes taxes & fees
17 Mar - 18 Mar
Knot One- Balcony View of ICW- Dog Friendly!
Property grounds

Holiday Home in Willoughby Spit

Beachfront Bungalow w/ BEST Location in Ocean View!
8.6 out of 10, Excellent, (7 reviews)
"Cute little bungalow on the beach. Beautiful sunrises. Location is great. Very clean. Has everything you need!!! The pier is a 2 min walk. "
United States
Virginia T.
The price is HK$774
HK$1,751 total
includes taxes & fees
11 Mar - 12 Mar
Beachfront Bungalow w/ BEST Location in Ocean View!
Property grounds

Apartment in Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
10.0 out of 10, Exceptional, (2 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$634
HK$1,454 total
includes taxes & fees
15 Mar - 16 Mar
Private 1 Bed Apt - Historic Olde Towne Portsmouth
2 bedrooms, iron/ironing board, WiFi, bed sheets

Apartment in East Ocean View

Sojourn's Harborage unit 6
9.2 out of 10, Wonderful, (5 reviews)
"Very comfortable - beds were soft, sheets were great and water pressure was nice. There was a problem with city drains so the parking lot was flooded a couple nights, which caused a lot of dirt to be tracked into the unit, but this wasn't a problem with the rental. Location was close to everything we needed."
United States
Ronald K.
The price is HK$571
HK$2,654 total
includes taxes & fees
24 Mar - 25 Mar
Sojourn's Harborage unit 6
Beach

Apartment in Willoughby Spit

Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
10.0 out of 10, Exceptional, (2 reviews)
"very friendly host! very patient with me on day of check in, made sure we had everything we needed & more !"
United States
Shydymond B.
The price is HK$469
HK$743 total
includes taxes & fees
31 Mar - 1 Apr
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
On the beach, sun-loungers

Holiday Home in Willoughby Spit

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
8.8 out of 10, Excellent, (73 reviews)
"Clean well equipped for a nice getaway "
United States
Sheila H.
The price is HK$774
HK$1,724 total
includes taxes & fees
11 Mar - 12 Mar
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
2 bedrooms

Apartment in Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is HK$842
HK$2,137 total
includes taxes & fees
11 Mar - 12 Mar
Ice Ice Baby Downtown Newport News
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
"This hotel is conveniently located and with all the amenities needed. Beachfront with the best view and private balcony. The room, hotel, and common areas were the cleanest I’ve ever seen. I have placed this hotel on my top pick list of places to stay in Virginia Beach. I’m very particular about my room and it was evident that cleanliness and attention to detail is a top priority at Hyatts Place. "
Sharon 1-night trip
Posted 3 hours ago
Hyatt Place Virginia Beach / Oceanfront