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Browse Select Chesapeake Vacation Homes

Our top choices for Chesapeake vacation homes

Your own private beach with this charming 3-bedroom beachfront house!

9.6 out of 10, Exceptional, (19)
"We had a great time!! 55yr anniversary our daughter, son inlaw & 2 great grand kids joined us for a couple days!!!"
Your own private beach with this charming 3-bedroom beachfront house!

Charming Tiny Cottage

10.0 out of 10, Exceptional, (43)
"This place is very nice, very clean, modern, private. "
Charming Tiny Cottage

The Art Door only minutes from beach

9.8 out of 10, Exceptional, (89)
"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"
The price is CA $139
CA $322 total
includes taxes & fees
Aug 26 - Aug 27
The Art Door only minutes from beach

BRAND NEW 4-bedroom home in the 4X4, Corolla, NC. A truly unique getaway!

BRAND NEW 4-bedroom home in the 4X4, Corolla, NC. A truly unique getaway!

Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.

10.0 out of 10, Exceptional, (255)
"Property was convenient to convention center and you can walk to the beach."
Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

9.8 out of 10, Exceptional, (178)
"This house was perfect for my family. The location was beautiful "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

10.0 out of 10, Exceptional, (152)
"With two adults and 16 high school seniors, this house was perfect! Enough big spaces to gather but enough smaller spaces to get away from the group. The pool was great and the location perfect. "
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

7.2 out of 10, Good, (7)
"Wonderful property!! My family and I had a great time. The location is very convenient to about everything. "
The price is CA $415
CA $777 total
includes taxes & fees
Sep 9 - Sep 10
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Oceanfront home “Sea Watch” ~~brand new pool

2.0 star property
10.0 out of 10, Exceptional, (16)
"Beautiful place, a relaxed vibe and a beach for your backyard, what could be better?"
Oceanfront home “Sea Watch” ~~brand new pool

Surfside Beach Cottage- steps from Virginia Beach Boardwalk!

10.0 out of 10, Exceptional, (33)
"We enjoyed our stay! The Beach and location was close enough to take the Dolphin boat tour and walk to restaurants. The only thing that would have been good was cleaning products to clean the tub. "
Surfside Beach Cottage- steps from Virginia Beach Boardwalk!

Coastal Luxury Canal Retreat • Luxury Amenities • Pool • Hot Tub • Walk to Beach

9.2 out of 10, Wonderful, (5)
Coastal Luxury Canal Retreat • Luxury Amenities • Pool • Hot Tub • Walk to Beach

Serenity on the Bay-Complimentary Sunrise & Sunset Views

9.6 out of 10, Exceptional, (45)
"Great place, very clean, plenty of room for a large family.Location was good and property & view of the water were very nice. Easy to get to and many restaurants and stores nearby. Highly recommend this place for your next visit. "
Serenity on the Bay-Complimentary Sunrise & Sunset Views

10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

9.4 out of 10, Exceptional, (102)
"Lots of space and the third floor is a great place to hang out with a big group. Ocean is a quick walk away. But lots of things that we were expecting to be functional did not work. Upon arrival we were sent a message documenting a list of things that were broken, which was disappointing. The hot tub also turned out to be out of order. Still a good stay for a big group, but some love needs to be put into the house. "
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

9.0 out of 10, Wonderful, (62)
"Great stay "
The price is CA $276
CA $492 total
includes taxes & fees
Sep 7 - Sep 8
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

9.6 out of 10, Exceptional, (63)
"It was a great place to stay!!! We had a great time."
Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

New Listing! Beachfront/Pool/Hot Tub

10.0 out of 10, Exceptional, (5)
"This property has it all. 10 beds, a bathroom for everyone, big kitchen, two separate decks with views of the ocean, and most importantly lots of private outdoor space and activities. Hot tub, ping pong, outdoor pool, giant chess, fireplace, kayaks, surf board, beach equipment, you name it. Host was responsive and this house has the best welcome packet I’ve ever had from a rental."
New Listing! Beachfront/Pool/Hot Tub

Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

9.6 out of 10, Exceptional, (121)
"We stayed at Lightly Salted last week; my family of five [2 adults, 3 kids (11, 5, 1)]and out close friends family of three [2 adults, 1 kid (3)]. "
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views

10.0 out of 10, Exceptional, (77)
"Beautiful house! perfect location! house stocked with everything you need! Cathy was the best host we have ever had!! We will definitely be back! Highly recommend booking!"
Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views

Beachfront Bungalow w/ BEST Location in Ocean View!

10.0 out of 10, Exceptional, (1)
"This place was a great stay for my friends and I, right on the beach and a very quiet area. The house was clean and the beds were very comfortable. George was very responsive with any questions we had. Will be back!"
The price is CA $276
CA $495 total
includes taxes & fees
Sep 10 - Sep 11
Beachfront Bungalow w/ BEST Location in Ocean View!

STEPS FROM THE WATER! BEAUTIFUL NEW HOME IN THE HEART OF 4x4 WILD HORSE CAROVA

9.8 out of 10, Exceptional, (24)
"Property is new and clean in a great location. We could see the ocean from the kitchen/living room and saw horses from the house multiple days. The arcade games and shuffle board table were big hits too! Excellent, proactive communication from the owner. All contributed to a great stay!"
STEPS FROM THE WATER! BEAUTIFUL NEW HOME IN THE HEART OF 4x4 WILD HORSE CAROVA
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