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Our top choices for Chesapeake vacation homes

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, (45 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is ¥25,842
¥47,914 total
includes taxes & fees
Apr 22 - Apr 23
3-bedroom home away from home in fabulous Chesapeake, Virginia.

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, (110 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is ¥15,848
¥36,056 total
includes taxes & fees
Apr 23 - Apr 24
The Art Door Duplex only minutes from beach

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.
The price is ¥16,316
¥62,271 total
includes taxes & fees
Apr 27 - Apr 28
Sojourn | Coastal Cottage | 3 BR

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 ¥12,707
¥40,812 total
includes taxes & fees
Apr 29 - Apr 30
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, (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 ¥15,864
¥45,355 total
includes taxes & fees
Apr 20 - Apr 21
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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

#Buckroe Bungalow ~Escape to the Beach 2mins Away!
Hampton
9.2 out of 10, Wonderful, (19 reviews)
"Enjoyed our staycation .Will be back."
United States
Josie B.
The price is ¥17,823
¥55,835 total
includes taxes & fees
Apr 21 - Apr 22
#Buckroe Bungalow ~Escape to the Beach 2mins Away!

Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
The price is ¥24,129
¥83,161 total
includes taxes & fees
Apr 21 - Apr 22
Unique Luxurious Waterfront in Hampton

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 ¥20,623
¥53,019 total
includes taxes & fees
Apr 20 - Apr 21
Cozy Beach Home in Oceanview

Comfort near the water and University

Comfort near the water and University
Elizabeth city
7.6 out of 10, Good, (5 reviews)
"The host was welcoming, very clean, and quiet area. Ty"
United States
Hector S.
The price is ¥11,898
¥45,174 total
includes taxes & fees
Apr 20 - Apr 21
Comfort near the water and University

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 ¥18,812
¥40,349 total
includes taxes & fees
Apr 21 - Apr 22
Knot Three- Balcony View of ICW- Dog Friendly!

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 ¥23,637
¥45,536 total
includes taxes & fees
Apr 20 - Apr 21
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

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 ¥15,864
¥29,666 total
includes taxes & fees
May 3 - May 4
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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 ¥19,846
¥39,717 total
includes taxes & fees
Apr 20 - Apr 21
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

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 ¥42,404
¥86,297 total
includes taxes & fees
Apr 27 - Apr 28
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

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 ¥21,416
¥138,622 total
includes taxes & fees
Apr 23 - Apr 24
Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach

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 ¥22,993
¥61,520 total
includes taxes & fees
Apr 27 - Apr 28
Carrick Bend -Balcony View of ICW- Dog Friendly!

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 ¥37,836
¥90,693 total
includes taxes & fees
Apr 20 - Apr 21
Wooded Wonderland

Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

Waterview Cottage on the Currituck Sound with Private Dock & Kayaks
Coinjock
10.0 out of 10, Exceptional, (38 reviews)
"Very nice house and super clean. Would recommend for anyone to stay here. 10/10 "
United States
christian t.
The price is ¥50,923
¥84,425 total
includes taxes & fees
May 8 - May 9
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

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 ¥28,412
¥52,487 total
includes taxes & fees
Apr 26 - Apr 27
Beachfront Bungalow w/ BEST Location in Ocean View!
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

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
435
Accommodation
1321 Vacation Homes
Lowest Price
¥23,484
Highest Price
¥138,622