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

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

10.0 out of 10, Exceptional, (222)
"Such a great house! Wonderful location for our family as we stayed for Thanksgiving week. Beautifully outfitted kitchen for us to prepare for Thanksgiving. (Even have a crockpot!) Our two dogs loved watching TV with us downstairs and loved looking out the windows to spot squirrels in the yard. The fenced in yard worked out wonderfully for us, too. We would love to return!"
Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.

Serenity on the Bay-Complimentary Sunrise & Sunset Views

9.4 out of 10, Exceptional, (26)
"Beautiful property"
Serenity on the Bay-Complimentary Sunrise & Sunset Views

The Art Door only minutes from beach

9.8 out of 10, Exceptional, (61)
"The property was clean and comfortable. Great location for us. Small backyard for our pet was perfect. Host was approachable and accommodating. Would recommend."
The price is AED 408
AED 886 total
includes taxes & fees
30 Dec - 31 Dec
The Art Door only minutes from beach

{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

9.0 out of 10, Wonderful, (20)
"We enjoyed our visit. This house was very clean and the host was really helpful. "
The price is AED 338
AED 1,122 total
includes taxes & fees
30 Dec - 31 Dec
{Beach Baby Bingo} Perfect Spot for Exploring Va. Beach

Entire Home - Pet Friendly - Close to Beach - 2 Guests

10.0 out of 10, Exceptional, (95)
"Always a great stay at this home! Highly recommend!"
Entire Home - Pet Friendly - Close to Beach - 2 Guests

Pristine North End Oceanside Home is Steps from the Beach

10.0 out of 10, Exceptional, (187)
"Family 2-61 stayed. We had a lovely time! Walking distance to the beach. It was quick and easy. No busy streets to cross. A very large space to spread out and enjoy each others company. Thank you!!"
Pristine North End Oceanside Home is Steps from the Beach

Big Beautiful Beachfront House! 5 bed/3.5 bath directly on the beach!

9.4 out of 10, Exceptional, (13)
"Wonderful place to spend tbe weekend!"
Big Beautiful Beachfront House! 5 bed/3.5 bath directly on the beach!

Inviting oceanfront home with amazing views, private pool & deck

8.4 out of 10, Very Good, (30)
"Positively beautiful view, excellent location, layout great. Bathrooms and Kitchen were clean and well maintained. Some suggestions: put a handrail at pool steps, vents,especially on wall in living room were filthy. Outside windows covered with bugs. Beach chairs and umbrella were all broken. For some reason hot water came out of both faucets in both masters. Minor changes would really enhance one’s stay but otherwise an enjoyable week."
Inviting oceanfront home with amazing views, private pool & deck

Dog-friendly home w/private pool and washer/dryer, WiFi, central AC, patio, deck

9.4 out of 10, Exceptional, (28)
"This is definitely a great place to stay! Other than a few oddities (front screen door, back door) everything was wonderful!. The Pool, the spaciousness, the bathrooms! Definitely will be booking this place again! "
Dog-friendly home w/private pool and washer/dryer, WiFi, central AC, patio, deck

STEPS FROM THE WATER! BEAUTIFUL NEW HOME IN THE HEART OF A WILD HORSE COMMUNITY!

9.8 out of 10, Exceptional, (15)
"Great location away from the hustle and bustle. Relaxing beach visit."
STEPS FROM THE WATER! BEAUTIFUL NEW HOME IN THE HEART OF A WILD HORSE COMMUNITY!

VB Paradise / Private Pool, Hot Tub

9.6 out of 10, Exceptional, (15)
"Home had the perfect layout for 4 couples and 1 single adult. Plenty of room for every to be together in the kitchen or family room with an additional “den” room we used as the “football room”. Kitchen was well stocked, towels were soft & absorbent, grill was full of gas & all the additional activities were easily accessible. Ryan the host couldn’t have been more helpful. Sending links for activities prior to our arrival, breakfast spot recommendations the 1st morning post arrival etc. Very...
The price is AED 1,657
AED 5,230 total
includes taxes & fees
1 Jan - 2 January 2025
VB Paradise / Private Pool, Hot Tub

Sojourn Aviators Dream on Back River

9.6 out of 10, Exceptional, (14)
"We picked this location given friends live nearby, but it exceeded expectations. Beautiful view, incredible sunrise, and the kids loved the fireplace. Hadn't realized the kids bunk room doesn't have a door to close, but luckily noise wasn't a problem. "
The price is AED 470
AED 1,421 total
includes taxes & fees
30 Dec - 31 Dec
Sojourn Aviators Dream on Back River

Wooded Wonderland

9.6 out of 10, Exceptional, (8)
"Great property. Pool, hot tub and a very challenging mini putt-putt course. Furniture is in good shape and comfortable. One of the bedrooms has an adjustable bed ( same model as I have at home) so that was a very nice and welcomed surprise. We have ongoing business in the area so looking forward to staying here in the future. "
The price is AED 716
AED 1,772 total
includes taxes & fees
7 Jan - 8 January 2025
Wooded Wonderland

Beach Vacation Home 1.5 Blocks from Beach

9.8 out of 10, Exceptional, (40)
"Comfort, quiet "
Beach Vacation Home 1.5 Blocks from Beach

Elizabeth City Vacation Rental: Gazebo w/ Hot Tub!

10.0 out of 10, Exceptional, (22)
"This was a great property and exactly what i needed for our trip."
Elizabeth City Vacation Rental: Gazebo w/ Hot Tub!

Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach

9.6 out of 10, Exceptional, (92)
"Myself, my husband and my son really enjoyed our stay. Very nice and quiet area for rest and relaxation. Beautiful walk to the beach along the canopy of trees walkway. Right next to the military base so felt very safe as well. Wish there was more availability for future visits but property appears booked for the next 2 years."
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach

Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning

7.0 out of 10, Good, (2)
"Our stay was okay. The house was in an excellent location to the beach, however very difficult to find from the road. The house was a great size & the beds were so comfortable. I rate this with a 3 because I felt like there were several things that desperately need updated. The faucets in the bathroom were heavily rusted and leaking. When taking a shower, our faucet diverter broke so we werent able to take a shower the last day of our stay. There is not much of an ocean view as there is a lot of...
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning

Private Estate on 4 Acres

9.2 out of 10, Wonderful, (28)
"This house was perfect for our extended family vacation. The house is very old but the owners made a lot very nice improvements. You can tell there are more things to do though. Communication was not that great but they were very nice when we did hear from them. Super easy check in"
Private Estate on 4 Acres

Beachfront/Pool/Hot Tub/Dog Friendly/Winter Specials

9.6 out of 10, Exceptional, (21)
"Plenty of room for everyone. The kids have lots to do and space of their own. Beach was beautiful and could see the sunrise every morning. We all had a lovely time "
Beachfront/Pool/Hot Tub/Dog Friendly/Winter Specials

Luxurious Beach Home with Indoor Pool Access! Steps from the Beach

8.6 out of 10, Excellent, (92)
"This was our 3rd cousins vacation and this was our 3rd house together, our only complaint is one of the rooms with bunkbeds didn't have any privacy and you had to walk through the space to get to the other 2 bedrooms "
Luxurious Beach Home with Indoor Pool Access! Steps from the 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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Other property types in Chesapeake

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very Good, (1418)
"Spacious rooms. Fully stocked kitchen. Working sauna."
The price is AED 323
AED 590 total
includes taxes & fees
9 Jan - 10 January 2025
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

The Ocean Key Resort by VSA Resorts

3.0 star property
7.8 out of 10, Good, (1277)
"My daughter had a wonderful time with her friends in the pool for her Birthday! The definitely enjoyed themselves!"
The price is AED 248
AED 503 total
includes taxes & fees
12 Jan - 13 January 2025
The Ocean Key Resort by VSA Resorts

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very Good, (1292)
"Great stay at a great price."
The Atrium Resort, Virginia Beach by Vacatia
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.