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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Chesapeake vacation homes

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 AED 648
AED 1,171 total
includes taxes & fees
8 Jun - 9 Jun
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Outdoor dining

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
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 AED 492
AED 1,015 total
includes taxes & fees
1 Jun - 2 Jun
Knot Three- Balcony View of ICW- Dog Friendly!
Exterior

Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing

Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing
Elizabeth City
The price is AED 337
AED 589 total
includes taxes & fees
28 May - 29 May
Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing
Exterior

Cozy 2-bedroom house in tranquil Elizabeth City with AC. Kick back with us.

Cozy 2-bedroom house in tranquil Elizabeth City with AC. Kick back with us.
Elizabeth City
The price is AED 410
AED 629 total
includes taxes & fees
31 May - 1 Jun
Cozy 2-bedroom house in tranquil Elizabeth City with AC. Kick back with us.
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 AED 408
AED 1,113 total
includes taxes & fees
3 Jun - 4 Jun
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
On the beach, sun loungers

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Willoughby Spit
8.8 out of 10, Excellent, (76 reviews)
"Clean well equipped for a nice getaway "
United States
Sheila H.
The price is AED 658
AED 1,211 total
includes taxes & fees
29 May - 30 May
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Dining

Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.8 out of 10, Exceptional, (17 reviews)
"This was a beautiful property. Plenty of room for Family Fun and very close to the beach. The host was very helpful and communicated with us about the property. I would definitely stay here again. "
United States
Tamika H.
The price is AED 746
AED 1,795 total
includes taxes & fees
28 May - 29 May
Beach Bungalow King Bed 1 Floor Living
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
9.6 out of 10, Exceptional, (4 reviews)
"It’s was great staying "
United States
Shalena K.
The price is AED 551
AED 911 total
includes taxes & fees
28 May - 29 May
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Smart TV, fireplace

Comfort near the water and University

Comfort near the water and University
Elizabeth city
8.0 out of 10, Very Good, (7 reviews)
"The host was welcoming, very clean, and quiet area. Ty"
United States
Hector S.
The price is AED 257
AED 1,046 total
includes taxes & fees
1 Jun - 2 Jun
Comfort near the water and University
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 AED 477
AED 1,223 total
includes taxes & fees
28 May - 29 May
Cozy Beach Home in Oceanview
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 AED 327
AED 1,008 total
includes taxes & fees
16 Jun - 17 Jun
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Beach nearby

Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach

Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach
Corolla
9.8 out of 10, Exceptional, (21 reviews)
"Host was great. Everything was as described "
United States
Kevin O.
Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach
Fridge, microwave, oven, stovetop

4 Bedroom Cottage - 5 Minutes from both beaches

4 Bedroom Cottage - 5 Minutes from both beaches
Hampton
9.4 out of 10, Exceptional, (29 reviews)
"The host was very accommodating. Our family had an emergency and we needed a place to stay in close proximity to the hospital. Although this listing said no pets, she allowed us to bring our pets. We are so appreciative. The house was beautiful and very clean. Thank you for our stay."
United States
Ty V.
The price is AED 800
AED 1,975 total
includes taxes & fees
28 May - 29 May
4 Bedroom Cottage - 5 Minutes from both beaches
Smart TV

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay,host was very hospital.love to enjoy it again in December "
United States
earnest d.
The price is AED 496
AED 1,371 total
includes taxes & fees
4 Jun - 5 Jun
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Property grounds

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
9.0 out of 10, Wonderful, (15 reviews)
"Great view and close to "
United States
Julian M.
The price is AED 658
AED 1,215 total
includes taxes & fees
2 Jun - 3 Jun
Beachfront Bungalow w/ BEST Location in Ocean View!
Interior

Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area
Wythe
7.8 out of 10, Good, (10 reviews)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is AED 436
AED 1,036 total
includes taxes & fees
28 May - 29 May
Large 2 bedroom | Queen beds | Safe Area
Terrace/patio

Carrick Bend -Balcony View of ICW- Dog Friendly!

Carrick Bend -Balcony View of ICW- Dog Friendly!
Coinjock
8.0 out of 10, Very Good, (1 review)
The price is AED 750
AED 1,749 total
includes taxes & fees
8 Jun - 9 Jun
Carrick Bend -Balcony View of ICW- Dog Friendly!
Interior

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
The price is AED 674
AED 1,505 total
includes taxes & fees
9 Jun - 10 Jun
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Game room

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very nice! And the host was in full contact with us throughout our stay to make sure we had everything we needed. Also, our family LOVED the video games. "
United States
Elaine P.
The price is AED 863
AED 2,274 total
includes taxes & fees
31 May - 1 Jun
Centrally Located Hampton Roads Home w/ Game Room!
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 Hotel Reviews

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

6/10 Okay
"Book a king size bedroom was given a two double bedroom and charge for the state of a king size bedroom. Rooms are not cleaned on the daily basis, but towels is replenished. Overall, the staff was nice and accommodating. The hotel inside and out was fairly clean. The hot tub could not be used. The pool is not open until 1 PM and close at 10 PM. The walls of extremely thin. The breakfast was better than most places I’ve been."
Linda 2-night trip
Posted 1 hour ago
Wingate by Wyndham Chesapeake