Holiday Homes in Chesapeake

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Our top choices for Chesapeake holiday homes

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.
3-bedroom home away from home in fabulous Chesapeake, Virginia.

Holiday Home in Northeast Virginia Beach

The Art Door Duplex only minutes from 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 €201
includes taxes & fees
23 Mar - 24 Mar
The Art Door Duplex only minutes from beach
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 €267
includes taxes & fees
18 Apr - 19 Apr
Knot Three- Balcony View of ICW- Dog Friendly!

Holiday Home in Willoughby Spit

Sojourn | Coastal Cottage | 3 BR
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 €374
includes taxes & fees
23 Mar - 24 Mar
Sojourn | Coastal Cottage | 3 BR
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 €231
includes taxes & fees
21 Mar - 22 Mar
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
8.8 out of 10, Excellent, (8 reviews)
"Cute little bungalow on the beach. Beautiful sunrises. Location is great. Very clean. Has everything you need!!! The pier is a 2 min walk. "
United States
Virginia T.
The price is €231
includes taxes & fees
23 Mar - 24 Mar
Beachfront Bungalow w/ BEST Location in Ocean View!
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 €254
includes taxes & fees
23 Mar - 24 Mar
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
9.4 out of 10, Exceptional, (3 reviews)
"It’s was great staying "
United States
Shalena K.
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Holiday Home in Bayview

Cozy Beach Home in Oceanview
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 €290
includes taxes & fees
22 Mar - 23 Mar
Cozy Beach Home in Oceanview
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 €401
includes taxes & fees
22 Mar - 23 Mar
Beach Bungalow King Bed 1 Floor Living

Holiday Home in Marshall

Large cozy private room
Large cozy private room
8.0 out of 10, Very good, (1 review)
Carrick Bend -Balcony View of ICW- Dog Friendly!
9.6 out of 10, Exceptional, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is €463
includes taxes & fees
22 Mar - 23 Mar
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
9.4 out of 10, Exceptional, (28 reviews)
"Clean house. Very easy check in and out process. "
United States
Ryan P.
The price is €354
includes taxes & fees
23 Mar - 24 Mar
4 Bedroom Cottage - 5 Minutes from both beaches
7.8 out of 10, Good, (10 reviews)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is €238
includes taxes & fees
23 Mar - 24 Mar
Large 2 bedroom | Queen beds | Safe Area
The price is €444
includes taxes & fees
24 Mar - 25 Mar
Unique Luxurious Waterfront in Hampton
8.8 out of 10, Excellent, (73 reviews)
"Clean well equipped for a nice getaway "
United States
Sheila H.
The price is €220
includes taxes & fees
22 Mar - 23 Mar
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
8.8 out of 10, Excellent, (70 reviews)
"Amazing little cottage right on the water. Would love to stay again. "
United States
ROBYN B.
The price is €231
includes taxes & fees
22 Mar - 23 Mar
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Holiday Home in Fox Hill

Sojourn Aviators Dream on Back River
9.6 out of 10, Exceptional, (29 reviews)
"My family enjoyed the experience of staying near the water. The views were lovely! "
United States
Precious E.
The price is €411
includes taxes & fees
25 Mar - 26 Mar
Sojourn Aviators Dream on Back River
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 €769
includes taxes & fees
21 Mar - 22 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

Find out more about Chesapeake

Chesapeake Holiday Homes information

Number of reviews
553
Accommodation
1390 Holiday Homes
Lowest Price
€201
Highest Price
€769