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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 631
AED 1,147 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 484
AED 1,005 total
includes taxes & fees
1 Jun - 2 Jun
Knot Three- Balcony View of ICW- Dog Friendly!
Living area

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 430
AED 652 total
includes taxes & fees
4 Jun - 5 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 400
AED 1,105 total
includes taxes & fees
3 Jun - 4 Jun
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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 360
AED 615 total
includes taxes & fees
3 Jun - 4 Jun
Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing
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 643
AED 1,447 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Beach Home in Oceanview
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, (16 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 AED 658
AED 1,215 total
includes taxes & fees
1 Jun - 2 Jun
Beachfront Bungalow w/ BEST Location in Ocean View!
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)
"Everything was wonderful"
United States
Marc
The price is AED 349
AED 1,150 total
includes taxes & fees
8 Jun - 9 Jun
Comfort near the water and University
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
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, cozy, well prepared.Location!!!"
United States
Caleb J.
The price is AED 559
AED 1,072 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
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 455
AED 788 total
includes taxes & fees
22 Jun - 23 Jun
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
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 1,728 total
includes taxes & fees
1 Jun - 2 Jun
Carrick Bend -Balcony View of ICW- Dog Friendly!
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
10 Jun - 11 Jun
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Smart TV

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 681
AED 1,533 total
includes taxes & fees
8 Jun - 9 Jun
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Beach nearby

#Buckroe Bungalow ~Escape to the Beach 2mins Away!

#Buckroe Bungalow ~Escape to the Beach 2mins Away!
Hampton
8.8 out of 10, Excellent, (21 reviews)
"Enjoyed our staycation .Will be back."
United States
Josie B.
The price is AED 401
AED 1,293 total
includes taxes & fees
1 Jun - 2 Jun
#Buckroe Bungalow ~Escape to the Beach 2mins Away!
On the beach

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Willoughby Spit
8.8 out of 10, Excellent, (74 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is AED 951
AED 1,591 total
includes taxes & fees
14 Jun - 15 Jun
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
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.
Centrally Located Hampton Roads Home w/ Game Room!
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 629
AED 1,275 total
includes taxes & fees
15 Jun - 16 Jun
Large 2 bedroom | Queen beds | Safe Area
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 847
AED 2,025 total
includes taxes & fees
11 Jun - 12 Jun
4 Bedroom Cottage - 5 Minutes from both beaches
Combined shower/tub, hair dryer, towels, soap

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is AED 1,355
AED 2,508 total
includes taxes & fees
7 Jun - 8 Jun
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
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
"Booked this hotel for the hot tub, it was closed the entire time and we kept being told oh it’s going to be open “tomorrow”. Lies."
Jamie 2-night trip
Posted less than an hour ago
Wingate by Wyndham Chesapeake