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 €257
includes taxes & fees
19 May - 20 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 €227
includes taxes & fees
12 May - 13 May
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 €252
includes taxes & fees
11 May - 12 May
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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 €351
includes taxes & fees
11 May - 12 May
Sojourn | Coastal Cottage | 3 BR

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 €223
includes taxes & fees
10 May - 11 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.
#Buckroe Bungalow ~Escape to the Beach 2mins Away!

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.
Sojourn Aviators Dream on Back River

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 €274
includes taxes & fees
9 Jun - 10 Jun
Comfort near the water and University

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

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 €128
includes taxes & fees
12 May - 13 May
Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing

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)
"The host was very accommodating. Our family had an emergency and we needed a place to stay in close proximity to the hospital. Although this listing said no pets, she allowed us to bring our pets. We are so appreciative. The house was beautiful and very clean. Thank you for our stay."
United States
Ty V.
The price is €449
includes taxes & fees
11 May - 12 May
4 Bedroom Cottage - 5 Minutes from both beaches

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 €139
includes taxes & fees
12 May - 13 May
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 €286
includes taxes & fees
10 May - 11 May
Cozy Beach Home in Oceanview

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 €245
includes taxes & fees
10 May - 11 May
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

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, (20 reviews)
"Private stay/ clean house with plenty of beds to sleep in"
United States
Charlie B.
The price is €754
includes taxes & fees
10 May - 11 May
Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach

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 €512
includes taxes & fees
20 May - 21 May
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

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 €280
includes taxes & fees
10 May - 11 May
Beachfront Bungalow w/ BEST Location in Ocean View!

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

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)
Carrick Bend -Balcony View of ICW- Dog Friendly!

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 €205
includes taxes & fees
17 May - 18 May
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
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
400
Accommodation
1321 Holiday Homes
Lowest Price
€128
Highest Price
€754