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 NZ$538
includes taxes & fees
6 May - 7 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 NZ$445
includes taxes & fees
29 Apr - 30 Apr
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach
Virginia Beach
9.6 out of 10, Exceptional, (112 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is NZ$410
includes taxes & fees
11 May - 12 May
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 NZ$647
includes taxes & fees
26 Apr - 27 Apr
Sojourn | Coastal Cottage | 3 BR

#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 NZ$569
includes taxes & fees
27 Apr - 28 Apr
#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 NZ$570
includes taxes & fees
6 May - 7 May
Cozy Beach Home in Oceanview

Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
The price is NZ$888
includes taxes & fees
28 Apr - 29 Apr
Unique Luxurious Waterfront in Hampton

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.
The price is NZ$912
includes taxes & fees
28 Apr - 29 Apr
4 Bedroom Cottage - 5 Minutes from both beaches

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 NZ$318
includes taxes & fees
3 May - 4 May
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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 NZ$410
includes taxes & fees
6 May - 7 May
Knot Three- Balcony View of ICW- Dog Friendly!

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 NZ$494
includes taxes & fees
26 Apr - 27 Apr
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 NZ$915
includes taxes & fees
3 May - 4 May
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

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 NZ$248
includes taxes & fees
28 Apr - 29 Apr
Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing

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 NZ$596
includes taxes & fees
27 Apr - 28 Apr
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, (19 reviews)
"Private stay/ clean house with plenty of beds to sleep in"
United States
Charlie B.
The price is NZ$1,461
includes taxes & fees
28 Apr - 29 Apr
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 NZ$695
includes taxes & fees
27 Apr - 28 Apr
Carrick Bend -Balcony View of ICW- Dog Friendly!

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 NZ$484
includes taxes & fees
6 May - 7 May
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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 NZ$553
includes taxes & fees
26 Apr - 27 Apr
Beachfront Bungalow w/ BEST Location in Ocean View!

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 NZ$986
includes taxes & fees
27 Apr - 28 Apr
Wooded Wonderland

King Bed Beach House 10 mins from Beach

King Bed Beach House 10 mins from Beach
Hampton
The price is NZ$931
includes taxes & fees
26 Apr - 27 Apr
King Bed Beach House 10 mins from 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

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Chesapeake Holiday Homes information

Number of reviews
423
Accommodation
1321 Holiday Homes
Lowest Price
NZ$248
Highest Price
NZ$1,461