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Our top choices for Chesapeake vacation homes

Central Chesapeake Stay Near Mall, Trails & parks

Central Chesapeake Stay Near Mall, Trails & parks
Greenbrier
Central Chesapeake Stay Near Mall, Trails & parks

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 628
AED 1,122 total
includes taxes & fees
25 May - 26 May
3-bedroom home away from home in fabulous Chesapeake, Virginia.

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 1,016 total
includes taxes & fees
16 Jun - 17 Jun
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

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 378
AED 1,063 total
includes taxes & fees
26 May - 27 May
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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 488
AED 1,022 total
includes taxes & fees
26 May - 27 May
Knot Three- Balcony View of ICW- Dog Friendly!

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 1,354 total
includes taxes & fees
25 May - 26 May
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.6 out of 10, Exceptional, (29 reviews)
"We loved our stay here! The property is gorgeous, the rooms are bright and spacious, and the kitchen had everything we needed for a week long stay. The kids really loved being able to spend time in the back yard looking at the water and watching the jets fly overhead. Would definitely recommend and will rebook whenever we’re back in town! "
United States
Clare G.
The price is AED 605
AED 1,832 total
includes taxes & fees
26 May - 27 May
Sojourn Aviators Dream on Back River

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 317
AED 566 total
includes taxes & fees
26 May - 27 May
Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing

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
21 Jun - 22 Jun
Cozy 2-bedroom house in tranquil Elizabeth City with AC. Kick back with us.

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 1,240 total
includes taxes & fees
26 May - 27 May
Cozy Beach Home in Oceanview

Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.8 out of 10, Exceptional, (16 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 635
AED 1,719 total
includes taxes & fees
25 May - 26 May
Beach Bungalow King Bed 1 Floor Living

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 294
AED 1,092 total
includes taxes & fees
2 Jun - 3 Jun
Comfort near the water and University

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
9.2 out of 10, Wonderful, (13 reviews)
"Great view and close to "
United States
Julian M.
The price is AED 658
AED 1,224 total
includes taxes & fees
25 May - 26 May
Beachfront Bungalow w/ BEST Location in Ocean View!

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 559
AED 1,080 total
includes taxes & fees
26 May - 27 May
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

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 516
AED 1,146 total
includes taxes & fees
31 May - 1 Jun
Large 2 bedroom | Queen beds | Safe Area

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
27 May - 28 May
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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
26 May - 27 May
Carrick Bend -Balcony View of ICW- Dog Friendly!

Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
10.0 out of 10, Exceptional, (1 review)
"This was a great location, very relaxing and spacious. We even enjoyed the river behind the house. The only thing was there were limited cookware and no blinds in the living room but besides that everything was great.We’d definitely stay here."
United States
Zakia J.
The price is AED 582
AED 1,977 total
includes taxes & fees
2 Jun - 3 Jun
Unique Luxurious Waterfront in Hampton

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

Beachside Bliss Block from the Shore - Seahorse

Beachside Bliss Block from the Shore - Seahorse
East Ocean View
10.0 out of 10, Exceptional, (1 review)
The price is AED 694
AED 1,650 total
includes taxes & fees
31 May - 1 Jun
Beachside Bliss Block from the Shore - Seahorse
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