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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Chesapeake holiday 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, (43 reviews)
"This was a wonderful place that was perfect for girls trip! I would definitely recommend and stay again!!"
United States
Tabitha P.
The price is £220
includes taxes & fees
8 Apr - 9 Apr
3-bedroom home away from home in fabulous Chesapeake, Virginia.
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 £245
includes taxes & fees
29 Mar - 30 Mar
Cozy Beach Home in Oceanview
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
9.4 out of 10, Exceptional, (3 reviews)
"It’s was great staying "
United States
Shalena K.
The price is £152
includes taxes & fees
2 Apr - 3 Apr
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
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, (108 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is £182
includes taxes & fees
22 Apr - 23 Apr
The Art Door Duplex only minutes from beach
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 £187
includes taxes & fees
28 Mar - 29 Mar
Knot Three- Balcony View of ICW- Dog Friendly!
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, (70 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is £194
includes taxes & fees
31 Mar - 1 Apr
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Pool

Large cozy private room

Large cozy private room
Marshall
The price is £123
includes taxes & fees
28 Mar - 29 Mar
Large cozy private room
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.
The price is £329
includes taxes & fees
13 Apr - 14 Apr
Sojourn | Coastal Cottage | 3 BR
Beach nearby

#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 £282
includes taxes & fees
29 Mar - 30 Mar
#Buckroe Bungalow ~Escape to the Beach 2mins Away!
Smart TV, fireplace

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 £225
includes taxes & fees
9 Apr - 10 Apr
Comfort near the water and University
Smart TV, fireplace, books, stereo

Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
The price is £385
includes taxes & fees
30 Mar - 31 Mar
Unique Luxurious Waterfront in Hampton
Dining

Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.8 out of 10, Exceptional, (15 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.
Beach Bungalow King Bed 1 Floor Living
Property grounds

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
8.8 out of 10, Excellent, (8 reviews)
"Great view and close to "
United States
Julian M.
The price is £217
includes taxes & fees
2 Apr - 3 Apr
Beachfront Bungalow w/ BEST Location in Ocean View!
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, (74 reviews)
"Clean well equipped for a nice getaway "
United States
Sheila H.
The price is £205
includes taxes & fees
20 Apr - 21 Apr
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Interior

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 £374
includes taxes & fees
5 Apr - 6 Apr
Sojourn Aviators Dream on Back River
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 £207
includes taxes & fees
25 Apr - 26 Apr
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Exterior

Discount Feb/Mar Htd pool/hotub, firepit oceanview, Wild Horses, 6 bed 7 baths

Discount Feb/Mar Htd pool/hotub, firepit oceanview, Wild Horses, 6 bed 7 baths
Corolla
10.0 out of 10, Exceptional, (22 reviews)
"Great stay! Beautiful home and wonderful experience:)"
United States
Christopher O.
The price is £765
includes taxes & fees
29 Mar - 30 Mar
Discount Feb/Mar Htd pool/hotub, firepit oceanview, Wild Horses, 6 bed 7 baths
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)
"Great stay, host is very responsive to issues and concerns "
United States
Jackson H.
The price is £218
includes taxes & fees
22 Apr - 23 Apr
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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 £306
includes taxes & fees
28 Mar - 29 Mar
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, (17 reviews)
"Private stay/ clean house with plenty of beds to sleep in"
United States
Charlie B.
The price is £666
includes taxes & fees
29 Mar - 30 Mar
Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach
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

Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

10/10 Excellent
"The room was great. The staff was friendly and professional. The highlight was the morning breakfast and the evening happy hour. Job well done!"
Deron 1-night trip
Posted 1 hour ago
Embassy Suites by Hilton Hampton Convention Center

Find out more about Chesapeake

Chesapeake Holiday Homes information

Number of reviews
496
Accommodation
1390 Holiday Homes
Lowest Price
£123
Highest Price
£765