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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 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 1,160 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
2 Jun - 3 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 420
AED 640 total
includes taxes & fees
2 Jun - 3 Jun
Cozy 2-bedroom house in tranquil Elizabeth City with AC. Kick back with us.
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
Hair dryer, towels, soap, toilet paper

Serene 3-bedroom house in welcoming Smithfield with AC

Serene 3-bedroom house in welcoming Smithfield with AC
Smithfield
The price is AED 496
AED 1,576 total
includes taxes & fees
2 Jun - 3 Jun
Serene 3-bedroom house in welcoming Smithfield with AC
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 1,101 total
includes taxes & fees
3 Jun - 4 Jun
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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 331
AED 1,125 total
includes taxes & fees
9 Jun - 10 Jun
Comfort near the water and University
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 AED 551
AED 911 total
includes taxes & fees
2 Jun - 3 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
2 Jun - 3 Jun
Carrick Bend -Balcony View of ICW- Dog Friendly!
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
2 Jun - 3 Jun
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
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
2 Jun - 3 Jun
Beachfront Bungalow w/ BEST Location in Ocean View!
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
9 Jun - 10 Jun
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Interior

Hot Tub | 9 beds | Fenced Yard

Hot Tub | 9 beds | Fenced Yard
Downtown Hampton
5.2 out of 10, (7 reviews)
"The house served its purpose for a weekend stay. Quite a few quirks to the property. Close to downtown Hampton. "
United States
Regina P.
The price is AED 789
AED 2,148 total
includes taxes & fees
2 Jun - 3 Jun
Hot Tub | 9 beds | Fenced Yard
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 674
AED 1,526 total
includes taxes & fees
9 Jun - 10 Jun
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
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 823
AED 1,410 total
includes taxes & fees
7 Jun - 8 Jun
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
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
2 Jun - 3 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
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.
4 Bedroom Cottage - 5 Minutes from both beaches
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 641
AED 1,304 total
includes taxes & fees
15 Jun - 16 Jun
Large 2 bedroom | Queen beds | Safe Area
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

Schooner Inn

Schooner Inn

2/10 Terrible
"Couple was arguing for hours next door until rescue arrived. Toilet not working, hair on whirlpool"
FéLee 1-night trip
Posted 1 hour ago
Schooner Inn