Holiday Homes in Chesapeake

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Our top choices for Chesapeake holiday 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, (46 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is AU$437
includes taxes & fees
5 May - 6 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 AU$367
includes taxes & fees
4 May - 5 May
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

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 AU$560
includes taxes & fees
5 May - 6 May
Sojourn | Coastal Cottage | 3 BR

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 AU$404
includes taxes & fees
5 May - 6 May
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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, (73 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is AU$406
includes taxes & fees
4 May - 5 May
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

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 AU$344
includes taxes & fees
4 May - 5 May
Knot Three- Balcony View of ICW- Dog Friendly!

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

#Buckroe Bungalow ~Escape to the Beach 2mins Away!
Hampton
9.0 out of 10, Wonderful, (20 reviews)
"Enjoyed our staycation .Will be back."
United States
Josie B.
The price is AU$515
includes taxes & fees
4 May - 5 May
#Buckroe Bungalow ~Escape to the Beach 2mins Away!

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 AU$469
includes taxes & fees
5 May - 6 May
Cozy Beach Home in Oceanview

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 AU$688
includes taxes & fees
11 May - 12 May
Sojourn Aviators Dream on Back River

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
9.0 out of 10, Wonderful, (12 reviews)
"Great view and close to "
United States
Julian M.
The price is AU$464
includes taxes & fees
10 May - 11 May
Beachfront Bungalow w/ BEST Location in Ocean View!

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 AU$204
includes taxes & fees
5 May - 6 May
Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing

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.
The price is AU$656
includes taxes & fees
4 May - 5 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 AU$393
includes taxes & fees
4 May - 5 May
Comfort near the water and University

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 AU$754
includes taxes & fees
4 May - 5 May
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

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 AU$363
includes taxes & fees
4 May - 5 May
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

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

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 AU$698
includes taxes & fees
28 May - 29 May
5 Min Walk to the Beach • Spacious 3BR/2.5BA Home

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 AU$593
includes taxes & fees
4 May - 5 May
Carrick Bend -Balcony View of ICW- Dog Friendly!

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 AU$218
includes taxes & fees
6 May - 7 May
Cozy 2-bedroom house in tranquil Elizabeth City with AC. Kick back with us.

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 AU$518
includes taxes & fees
5 May - 6 May
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
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

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Chesapeake Holiday Homes information

Number of reviews
452
Accommodation
1321 Holiday Homes
Lowest Price
AU$204
Highest Price
AU$754