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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

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, (46 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is AED 724
AED 1,279 total
includes taxes & fees
19 May - 20 May
3-bedroom home away from home in fabulous Chesapeake, Virginia.
TV

The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach
Northeast Virginia Beach
9.6 out of 10, Exceptional, (111 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is AED 367
AED 835 total
includes taxes & fees
27 Apr - 28 Apr
The Art Door Duplex only minutes from beach
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 294
AED 966 total
includes taxes & fees
25 Apr - 26 Apr
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Dining

Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
Sojourn | Coastal Cottage | 3 BR
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, (26 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 367
AED 1,059 total
includes taxes & fees
23 Apr - 24 Apr
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Beach

5 Min Walk to the Beach • Spacious 3BR/2.5BA Home

5 Min Walk to the Beach • Spacious 3BR/2.5BA Home
East Ocean View
The price is AED 644
AED 1,647 total
includes taxes & fees
7 May - 8 May
5 Min Walk to the Beach • Spacious 3BR/2.5BA Home
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, (72 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is AED 474
AED 940 total
includes taxes & fees
23 Apr - 24 Apr
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
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 432
AED 921 total
includes taxes & fees
28 Apr - 29 Apr
Knot Three- Balcony View of ICW- Dog Friendly!
Smart TV, fireplace, books, stereo

Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
Unique Luxurious Waterfront in Hampton
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.
Cozy Beach Home in Oceanview
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, (75 reviews)
"Clean well equipped for a nice getaway "
United States
Sheila H.
The price is AED 460
AED 920 total
includes taxes & fees
23 Apr - 24 Apr
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Smart TV

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 367
AED 687 total
includes taxes & fees
3 May - 4 May
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Exterior

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 982
AED 1,994 total
includes taxes & fees
26 Apr - 27 Apr
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
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)
"Clean house. Very easy check in and out process. "
United States
Ryan P.
4 Bedroom Cottage - 5 Minutes from both beaches
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 524
AED 1,448 total
includes taxes & fees
27 Apr - 28 Apr
Carrick Bend -Balcony View of ICW- Dog Friendly!
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, (18 reviews)
"Private stay/ clean house with plenty of beds to sleep in"
United States
Charlie B.
The price is AED 496
AED 3,243 total
includes taxes & fees
27 Apr - 28 Apr
Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach
Living area

King Bed Beach House 10 mins from Beach

King Bed Beach House 10 mins from Beach
Hampton
The price is AED 783
AED 2,053 total
includes taxes & fees
23 Apr - 24 Apr
King Bed Beach House 10 mins from Beach
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, (9 reviews)
"Great view and close to "
United States
Julian M.
The price is AED 658
AED 1,211 total
includes taxes & fees
26 Apr - 27 Apr
Beachfront Bungalow w/ BEST Location in Ocean View!
Dining

Wooded Wonderland

Wooded Wonderland
Portsmouth
9.8 out of 10, Exceptional, (12 reviews)
"Easy check in. House very clean and well equipped. Comfortable stay"
United States
Nona C.
The price is AED 909
AED 2,142 total
includes taxes & fees
27 Apr - 28 Apr
Wooded Wonderland
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

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

6/10 Okay
"The pools and Skybar were closed for our stay Large group staying at property was inconvenient by overcrowding the elevators and making them malfunction "
Okeshia 2-night trip
Posted 3 hours ago
Hilton Virginia Beach Oceanfront