Holiday Homes in Chesapeake

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Featured Holiday Homes in Chesapeake

Charming Tiny Cottage

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

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!

A MINI PARADISE-"THE FRISKY DOLPHIN"PRIVATE BEACH- 3BED, 2BATH!!

9.6 out of 10, Exceptional, (167)
"Great location. Listing was accurate. "
A MINI PARADISE-"THE FRISKY DOLPHIN"PRIVATE BEACH- 3BED, 2BATH!!

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

Oceanfront home “Sea Watch” ~~brand new pool

2.0 star property
10.0 out of 10, Exceptional, (15)
"Beautiful place, a relaxed vibe and a beach for your backyard, what could be better?"
Oceanfront home “Sea Watch” ~~brand new pool

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 NZ$588
includes taxes & fees
8 Sept - 9 Sept
Beachfront Bungalow w/ BEST Location in Ocean View!

Breathtaking Sunsets On Back Bay- Your Sandbridge Escape Awaits!

9.6 out of 10, Exceptional, (215)
"Spent a few days in Sandbridge for a local event. Great quiet place with nice sunsets."
Breathtaking Sunsets On Back Bay- Your Sandbridge Escape Awaits!

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

9.8 out of 10, Exceptional, (16)
"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!

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

Semi-Oceanfront , Views! 5 BR Pet Friendly, Pool, Hot Tub, Location!

8.8 out of 10, Excellent, (139)
"We thoroughly enjoyed our stay and the rest and relaxation was greatly appreciated!"
Semi-Oceanfront , Views! 5 BR Pet Friendly, Pool, Hot Tub, Location!

Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

4.0 star property
7.4 out of 10, Good, (42)
"First want to start off by saying the house is as described actually better then the photos online led us to believe. It's an older house but was clean and decorated beautifully. For the money, description, and space you get staying in this home I would definatley recomend you staying here. It's not a 5 star luxury resort, but I gave 5 stars for the house being it was better then what we expected. Our family enjoyed our stay."
The price is NZ$614
includes taxes & fees
2 Sept - 3 Sept
Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

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 NZ$946
includes taxes & fees
3 Sept - 4 Sept
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Beach Cottage a short walk from the waves!

9.2 out of 10, Wonderful, (24)
"Me and my family had a wonderful time staying here on Carova Beach. This place was clean and ready to go for visitors and had everything needed to enjoy a nice secluded stay on the beach! Thanks!"
Beach Cottage a short walk from the waves!

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

10.0 out of 10, Exceptional, (254)
"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.

TownHome 3blks Boardwalk

10.0 out of 10, Exceptional, (2)
"We had the best time. The townhouse is perfect — plenty of space. Excellent layout. Location is PERFECT just a quick walk to the beach. Lots of restaurants nearby. Free parking. Bedrooms/ beds / bathrooms / kitchen all excellent. "
The price is NZ$719
includes taxes & fees
17 Aug - 18 Aug
TownHome 3blks Boardwalk

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

OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

9.8 out of 10, Exceptional, (48)
"Wonderful trip with an awesome house. Very quiet and the house is beautiful. Lots of room. Thank you so much."
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

9.8 out of 10, Exceptional, (105)
"We stayed as a family for our spring break. House was clean, beds were comfortable, and location was great! The kids loved seeing wild horses right off the deck and we found more by driving around. We spent one day on the beach and that was a lot of fun. Weather was a bit chilly, but nothing we could control!"
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach

9.6 out of 10, Exceptional, (118)
"Great location and accomadations"
Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach

The Art Door only minutes from beach

9.6 out of 10, Exceptional, (85)
"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 NZ$390
includes taxes & fees
25 Aug - 26 Aug
The Art Door only minutes 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