Search Vacation Homes in Chesapeake

Most properties are fully refundable. Because flexibility matters.

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Search over 2.9 million properties and 550 airlines worldwide.

Find properties with these dates

Compare 1108 Vacation Homes in Chesapeake with updated reviews, rates, and availability.

Exterior
Private Inground Pool! 3 min walk to beach and dining. Dog friendly! Sleeps 14
10.0 out of 10, Exceptional, (1)
"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
Fridge, microwave, oven, stovetop
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 $114
$218 total
includes taxes & fees
May 16 - May 17
Hampton Centrally Located Oasis
Fridge, microwave, oven, stovetop
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!
Save an average of 15% on thousands of hotels when you're signed in
Fridge, microwave, oven, stovetop
A Calm Haven in a Beautiful City
10.0 out of 10, Exceptional, (1)
"The property host was awesome. Quick communication and ready to assist. Everything you need is here. Our stay at this property was great as all the shopping centers and food restaurants were so close and convenient."
A Calm Haven in a Beautiful City
Beach nearby, sun loungers, beach towels
Entire Home - Pet Friendly - Close to Beach - 2 Guests
10.0 out of 10, Exceptional, (75)
"This property is a perfect example of what a vacation rental should be. The hosts have thought of everything, and delivered beautifully. It was super clean, had high quality towels and bed linens, a well-stocked kitchen, quality paper products, comfortable bed, well-functioning appliances and a lovely beach-themed decor with unique wall hangings. The beach is less than 2 miles away, parking offstreet right outside the gate, nice fenced-in backyard, and a pet-friendly neighborhood I felt safe in....
Entire Home - Pet Friendly - Close to Beach - 2 Guests
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 $185
$361 total
includes taxes & fees
Jun 10 - Jun 11
Comfortable Home | Long Stay Discount Available
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!
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
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!
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
3 bedrooms, desk, iron/ironing board, travel crib
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
Property grounds
Beachfront/Pool/Outdoor Bar/Dog Friendly/$Specials
9.8 out of 10, Exceptional, (7)
"Great location"
Beachfront/Pool/Outdoor Bar/Dog Friendly/$Specials
Fridge, microwave, oven, stovetop
The Redwood House
9.8 out of 10, Exceptional, (19)
"Quick trip for youth sports. House was a good fit for our needs. Owner was very attentive and accomating to messages. He accomatee an extensiok for our stay and when chose not to, he voluntary refunded the extension. The act was not expected but definitely appreciated!"
The Redwood House
Property grounds
Breathtaking Ocean views at Pinch Me! 8bdrm, 6bath, private pool!
9.8 out of 10, Exceptional, (130)
"Had a good time. Check in was easy. Place was clean. Upstairs bedroom could use a ceiling fan. Host was responsive."
Breathtaking Ocean views at Pinch Me! 8bdrm, 6bath, private pool!
Pool
Lovely Town Home
9.6 out of 10, Exceptional, (57)
"We came for a wrestling tournament and had a great stay."
Lovely Town Home
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)
Exterior
Refreshed Pet-Friendly 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406B)
9.6 out of 10, Exceptional, (89)
"Overall positive experience. Comfortable and well maintained property. Location close to the beach."
Refreshed Pet-Friendly 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406B)
Fridge, microwave, oven, stovetop
Spacious 4 BR Townhouse Walking Distance to the Beach and Boardwalk (408B)
9.6 out of 10, Exceptional, (56)
"Awesome house and very very clean"
Spacious 4 BR Townhouse Walking Distance to the Beach and Boardwalk (408B)
Fridge, microwave, oven, stovetop
Newly Refreshed 4 BR Pet-Friendly Townhouse Walking Distance to the Beach and Boardwalk (404A)
9.6 out of 10, Exceptional, (57)
"The property was very clean and as described in the listing. The property manager was very communicative and provided a link to a guest portal to easily access need to know information throughout our stay. The location is very noisy, however, with street traffic at all hours. It didn’t bother us, but something worth considering."
Newly Refreshed 4 BR Pet-Friendly Townhouse Walking Distance to the Beach and Boardwalk (404A)
Fridge, microwave, oven, stovetop
Recently Remodeled Northend Home Just Steps From Beach With Pool Table
9.6 out of 10, Exceptional, (127)
"Was looking for a place to stay for myself along with a group of undergraduate students for participation in a competition at the nearby state park. This was a great spot, and the house layout made it easy for the students and I to have separate spaces."
Recently Remodeled Northend Home Just Steps From Beach With Pool Table
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, (91)
"This condo was absolutely fabulous. It is literally 2 minute walk to the beach access. The rooms were comfortable and I've never stayed at a Vrbo with such an impressively stocked kitchen. The host responded quickly and answered all our questions. They were also very responsive. It was a lovely stay."
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, (1077)
"The property staff was very nice and tentative to our needs during our stay. We had an issue with our room and they changed our room that was more suitable."
The price is $108
$178 total
includes taxes & fees
May 29 - May 30
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, (1269)
"View was immaculate. Room was accommodating. Some major amenities were not available during entire duration of stay (wi fi) and some ice machines. The ocean view made it worth the stay."
The price is $122
$199 total
includes taxes & fees
May 16 - May 17
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 Vacation Homes information

Number of reviews
763
Accommodation
1108 Vacation Homes
Lowest Price
$114
Highest Price
$185

Recent reviews of Chesapeake hotels
Expedia verified reviews