Holiday Homes in Chesapeake

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Featured Holiday Homes in Chesapeake and around

Property grounds
Private Inground Pool! 3 min walk to beach and dining. Dog friendly! Sleeps 14
10.0 out of 10, Exceptional, (2)
"The place had everything we needed. We stayed for four nights and were able to use the pool and walk to the beach. Thanks for a great stay!"
Private Inground Pool! 3 min walk to beach and dining. Dog friendly! Sleeps 14
Exterior
STEPS FROM THE WATER! BEAUTIFUL NEW HOME IN THE HEART OF A WILD HORSE COMMUNITY!
10.0 out of 10, Exceptional, (3)
"This house was exactly what we needed. Short walk to beach, clean, comfortable beds and the horses favored this location."
STEPS FROM THE WATER! BEAUTIFUL NEW HOME IN THE HEART OF A WILD HORSE COMMUNITY!
Dining
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, (3)
"Extras were a delightful touch, didn't need anything during our stay. Host was quick to respond, location was close to stores and everything we needed."
The price is €206
includes taxes & fees
23 May - 24 May
Hampton Centrally Located Oasis
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Fridge, microwave, oven, stovetop
Comfortable Home | Long Stay Discount Available
10.0 out of 10, Exceptional, (1)
"Anthane was an amazing host. The property was very comfortable and clean! We enjoyed our stay!"
The price is €339
includes taxes & fees
10 Jun - 11 Jun
Comfortable Home | Long Stay Discount Available
Fridge, microwave, oven, stovetop
Your own private beach!
10.0 out of 10, Exceptional, (81)
"Kat is an incredible host—so kind, so responsive and so generous. We needed to check in a bit early and check out a bit late and she went above and beyond to make sure we felt comfortable. The place is beautiful; spotless and is truly *right on the beach*. Because it was winter, the beach was almost entirely ours; our dog was sooo happy to roam and enjoy, and also loved the space, especially the screened in porch. If you’re looking for a tucked away place, especially in the winter, this is your...
Your own private beach!
Exterior
Oceanfront Luxury Home w/ Private Pool, Hot Tub, Game Room & More!
10.0 out of 10, Exceptional, (19)
"This property was an absolute dream. The house was gorgeous and had every amenity you could think of. The location and the view of the ocean was breathtaking. We saw dolphins and the horses came right up to the house on more than one occasion! Even the beach driving was a fun experience that I already miss. Will happily book at the Seashine in the years to come."
Oceanfront Luxury Home w/ Private Pool, Hot Tub, Game Room & More!
Fridge, microwave, oven, stovetop
Cozy Ocean Side Beach Cottage at Fantastic Location North End of Virginia Beach
10.0 out of 10, Exceptional, (68)
"It was a perfect spot for a girls weekend!!!"
Cozy Ocean Side Beach Cottage at Fantastic Location North End of Virginia Beach
Property grounds
The Art Door only minutes from beach
9.8 out of 10, Exceptional, (36)
"This cute little apartment is the perfect getaway spot and pet friendly! It was super clean and smelled fantastic. The fenced in backyard is perfect to just sit out and enjoy the warm weather, and to be outside with your dog! The bathroom is a great size and beautiful! The bed was very comfortable and the linens and towels were great quality. The living room and kitchen was an added bonus, although we didn’t use it much. The host was very responsive and attentive to our needs, offering to adjust...
The price is €244
includes taxes & fees
11 Jun - 12 Jun
The Art Door only minutes from beach
Property grounds
A block to the beach!
9.8 out of 10, Exceptional, (38)
"We were at a different location than we originally booked. I am not sure how to rate the place shown since we weren't there. The alternative home we did stay in was very nice, on the beach and easy to get to everywhere."
A block to the beach!
Fridge, microwave, oven, stovetop
Gorgeous Beach Views, 30 second walk to beach! Sleeps up to 10!
9.8 out of 10, Exceptional, (11)
"Perfect"
Gorgeous Beach Views, 30 second walk to beach! Sleeps up to 10!
Beach
Petit Cozy Beach Bungalow— 5 min walk to the beach
9.8 out of 10, Exceptional, (9)
"Nice quaint bungalow. Beds were nice and comfortable and the bathroom was also quite nice. It's close to the beach area and an easy walk. All positive about our stay there."
Petit Cozy Beach Bungalow— 5 min walk to the beach
Fridge, microwave, oven, stovetop
Renovated 2 Bedroom, near VB Vibe district, walk to the beach!
9.8 out of 10, Exceptional, (19)
"The place was great. The host was great. We were in town for a sporting event at convention center, which was walking distance, but we took advantage of what the town had to offer. Beach, playgrounds, unique shopping, food trucks, markets , restaurants, fishing …. All so very close. Wishing it was available for next months event! Maybe next year. Enjoy"
Renovated 2 Bedroom, near VB Vibe district, walk to the beach!
Smart TV, fireplace
SPRING SPECIAL !!!Canal Front - Paddle Board
9.8 out of 10, Exceptional, (30)
"We had a great week. Kevin was great and help us out when we needed it."
SPRING SPECIAL !!!Canal Front - Paddle Board
3 bedrooms, desk, iron/ironing board, travel cot
Norfolk Oasis
9.8 out of 10, Exceptional, (10)
"From the moment we walked in the door we were immediately greeted with the smell of freshly cleaned floors, linens, and counter tops. I was very impressed by the customer service of our hosts and the speed at which they responded to any of our questions. They were very kind and respectful as well. We were visiting from NY, and the house was pleasantly bigger than what we expected. They provided clean linens and basically everything we needed for the weekend. Will definitely recommend and stay...
Norfolk Oasis
Pool
Lovely Town Home
9.6 out of 10, Exceptional, (58)
"This is great property to stay in easy to get around the area close to a lot of amenities Very clean property and the owner was very easy to get in contact with"
Lovely Town Home
Beach nearby
Octopus Oasis on the 4x4 Beach Of Carova Very Private
9.6 out of 10, Exceptional, (4)
"The home was in tip top condition. New everything, including hot tub, appliances, all beds and pillows (high end excellent quality). It truly makes for a better experience having peace, quiet, clean and comfy bedding. The owners were truly a blessing, living nearby. They were the definition of true southern hospitality. They went above and beyond making our stay as comfortable as possible. I could not have asked for a better host from maintaining the hot tub, answering numerous questions about...
Octopus Oasis on the 4x4 Beach Of Carova Very Private
Property grounds
The Seashell Shack - Waterfront Tiny House on Back Bay
9.6 out of 10, Exceptional, (27)
"We enjoyed this tiny house for a quick Spring Break trip. Waking up to the views of the water was perfection! We highly recommend Baja, the restaurant next door, for dinner. Overall, this house was very clean & very updated; property manager Scott was great to work with."
The Seashell Shack - Waterfront Tiny House on Back Bay
Fridge, microwave, oven, stovetop
Spacious 4 BR Townhouse Walking Distance to the Beach and Boardwalk (412A)
9.6 out of 10, Exceptional, (98)
"Great. As described. Clean. Convenient. Close to beach. Close to shopping. Close to food!!"
Spacious 4 BR Townhouse Walking Distance to the Beach and Boardwalk (412A)
Fridge, microwave, oven, stovetop
Spacious 4 BR Townhouse Walking Distance to the Beach and Boardwalk (408B)
9.6 out of 10, Exceptional, (57)
"Awesome house and very very clean"
Spacious 4 BR Townhouse Walking Distance to the Beach and Boardwalk (408B)
Fridge, microwave, oven, stovetop
Beach Bungalow King Bed 1 Floor Living
9.6 out of 10, Exceptional, (5)
"The property is in a quaint neighborhood. We enjoyed seeing ducks in the yard, kicking back to tv, comfortable sleeping, and the aesthetics. The house was stocked with everything we needed."
Beach Bungalow King Bed 1 Floor Living
Don't see what you're looking for?
See all available properties in Chesapeake
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.

Other property types in Chesapeake

Beach
Beach Condo 2 Min Walk From The Beach
9.2 out of 10, Wonderful, (92)
"2min walk was th best! The house was fun!! Sunrise and sunset on th beach was incredible! Would definitely recommend and go again to this same place!"
Beach Condo 2 Min Walk From The Beach
Interior
The Atrium Resort by VSA Resorts
3.5 star property
8.2 out of 10, Very good, (1084)
"My 12 year old son requested we celebrate his birthday here becase the rooms are great, the staff is always helpful, location is perfect, the pool is always clean and heated. It's walking distance to everything at the ocean front so you can park and walk everywhere. Definatelty will be back!"
The price is €184
includes taxes & fees
28 May - 29 May
The Atrium Resort by VSA Resorts
Exterior
The Ocean Sands Resort by VSA Resorts
3.0 star property
8.0 out of 10, Very good, (1276)
"Clean, friendly and great location. "
The price is €213
includes taxes & fees
23 May - 24 May
The Ocean Sands Resort by VSA Resorts
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.

Chesapeake Holiday Homes information

Number of reviews
1,444
Accommodation
1095 Holiday Homes
Lowest Price
€184
Highest Price
€499

Recent Reviews in Chesapeake
Expedia verified reviews