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Compare 148 Cottages in Chesapeake with updated reviews, rates, and availability.

Shore Relaxing ocean views and wild horses Farm house cottage dog friendly

10.0 out of 10, Exceptional, (88)
"Beautiful, relaxing, dream home. Wild horses in your backyard! We loved it!"
Shore Relaxing ocean views and wild horses Farm house cottage dog friendly

Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided

10.0 out of 10, Exceptional, (182)
"Our annual trip is one of our favorite family traditions - the property is the perfect size for our little family, and we always leave refreshed and happy!"
Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided

Charming 3 BR North End Beach Cottage One Block to the Beach - Private Parking + Private Backyard

9.8 out of 10, Exceptional, (20)
"We had a wonderful time relaxing with friends in this cute, comfortable beach cottage. It was very clean, well stocked, and more spacious than we expected. Would definitely stay there again. "
Charming 3 BR North End Beach Cottage One Block to the Beach - Private Parking + Private Backyard

Cozy Mother-in-Law Suite

9.0 out of 10, Wonderful, (86)
"Perfect spot for a couple to relax. Property was as listed and very clean. I would definitely stay again!"
Cozy Mother-in-Law Suite

6 Block to oceanfront and in the center of the vibe district!

9.0 out of 10, Wonderful, (27)
"We had a great stay! Penny was a very accommodating host, going out of her way to help us with a few special needs we had traveling with a baby, and the house was comfortable and clean and in a fun neighborhood. Great location. Would highly recommend this as a stay for anyone in VB. "
6 Block to oceanfront and in the center of the vibe district!

Sophisticated waterfront Sandbridge cottage on Back Bay, minutes to the ocean.

10.0 out of 10, Exceptional, (11)
"We loved the covered outdoor patio."
Sophisticated waterfront Sandbridge cottage on Back Bay, minutes to the ocean.

Waterfront Willoughby Oasis

10.0 out of 10, Exceptional, (1)
"I just want to thank our host again and again. The communication was amazing and Audra was so accommodating for our last minute booking. We had to rush into town due to a family member’s death, but the house’s picture perfect location makes us want to go back under happier circumstances. "
Waterfront Willoughby Oasis

Beautiful Waterfront Vacation Rental on the Currituck Sound

9.8 out of 10, Exceptional, (71)
"The house had a nice large room upstairs and bathroom for brisdesmaids and bride to get ready. The balcony was used for groom first look. Great pictures taken here. Very nice home that was oerfect for the occasion"
Beautiful Waterfront Vacation Rental on the Currituck Sound

Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

9.0 out of 10, Wonderful, (96)
"The hosts were awesome, the house was very comfortable, beach access was perfect. We will be back!!"
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

New CANAL front home a few rows back from the OCEAN! Beach passes provided!

10.0 out of 10, Exceptional, (11)
"This property is beautiful and perfect for a relaxing stay. Interior is beautiful, location is perfect for beach days, and you might even get some surprise horse yard guest."
New CANAL front home a few rows back from the OCEAN! Beach passes provided!

Dogs Welcome! Cottage in Amenity-Filled Currituck NC Campground (J03)

9.8 out of 10, Exceptional, (31)
"Property is wonderful! We will definitely return! "
Dogs Welcome! Cottage in Amenity-Filled Currituck NC Campground (J03)

Comfortable & Private 2 Bedrm Cottage w/ King bed.

10.0 out of 10, Exceptional, (13)
"It was a great stay. Was there for work. Close for work and close to the beach. "
The price is AED 533
AED 1,316 total
includes taxes & fees
14 Jun - 15 Jun
Comfortable & Private 2 Bedrm Cottage w/ King bed.

The Surf Shack H2O! Radiant Rich Sunsets From Back Back Bay to Sandbridge Beach!

8.6 out of 10, Excellent, (14)
"been there before 4/5 times enjoyed the stay"
The Surf Shack H2O! Radiant Rich Sunsets From Back Back Bay to Sandbridge Beach!

Cozy Suite at the Beach

8.4 out of 10, Very Good, (58)
"Nice house"
Cozy Suite at the Beach

Pink Flamingo at the Beach

9.0 out of 10, Wonderful, (15)
"Great stay! Highly recommended!"
Pink Flamingo at the Beach

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

8.0 out of 10, Very Good, (3)
"It was an amazing weekend everyone is so nice around. the house is older but beautifull place to stay with your family the beech is Absolutely amazing. Hope we can rent this special gem again in the future "
Old Time Beach Front Cottage - The Beach is your Backyard! (Pet Friendly) by RedAwning

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 10, Good, (23)
"Wonderful owners with phenomenal communication. They were very patient and super responsive to messages. They went above and beyond to make us comfortable. Property had everything we needed and more and was steps from the ocean. The beach itself was private and not crowded at all. This was our 2nd time staying and will definitely not be our last."
Treetop Rustic Beach Front 2 Bedroom Apartment

Pet-Friendly Cottage in Amenity-Filled Currituck Sound Campground (J04)

9.6 out of 10, Exceptional, (37)
"Enjoyed the cottage!"
Pet-Friendly Cottage in Amenity-Filled Currituck Sound Campground (J04)

Sandy Mutts at the Beach

7.8 out of 10, Good, (12)
"It was a wonderful stay and our host was wonderful to work with. We will be back soon! "
Sandy Mutts at the Beach

Mermaid's and Mutts Retreat

9.0 out of 10, Wonderful, (31)
"Excellent location, very clean, host was very responsive and brought a hose so we could rinse the dog and ourselves. Would definitely stay again!"
Mermaid's and Mutts Retreat
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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