Search Cottages in Chesapeake

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 143 Cottages in Chesapeake with updated reviews, rates, and availability.

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

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (258)
"This property is in a great location for beach access and provided exactly what I needed for a holiday link up with my adult children. The homeowners were exceptional in their customer service, providing an introduction and being prompt and courteous to any questions. As a first time renter, this was appreciated."
The price is AEDĀ 643
AEDĀ 1,321 total
includes taxes & fees
7 May - 8 May
Norfolk Beach Cottage Rental

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

9.0 out of 10, Wonderful, (26)
"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!

Beautiful Waterfront Vacation Rental on the Currituck Sound

9.8 out of 10, Exceptional, (67)
"Excellent location, amazing view, very comfortable, and modern! "
Beautiful Waterfront Vacation Rental on the Currituck Sound

Charming Waterfront Cottage with Stunning Sunsets

10.0 out of 10, Exceptional, (17)
"My sons loved veing right on the water. We caught 6 fish in the little time we were there."
Charming Waterfront Cottage with Stunning Sunsets

Charming Beach Cottage Only 100 yds from the beach

9.4 out of 10, Exceptional, (48)
"The house had everything we needed to relax and enjoy our vacation. It was very clean and just a great place to stay. The very short walk to the beach was perfect too!! Not super close to the tourist attractions so it was wonderfully peaceful!"
Charming Beach Cottage Only 100 yds from the beach

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

10.0 out of 10, Exceptional, (10)
"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!

Josies Joint-New for 2024 Newly built only 3.5 Miles off Blacktop

10.0 out of 10, Exceptional, (2)
"Slice of paradise!"
Josies Joint-New for 2024 Newly built only 3.5 Miles off Blacktop

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

10.0 out of 10, Exceptional, (85)
"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, (181)
"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

Cozy Bay Cottage private backyard blocks from beach!

9.0 out of 10, Wonderful, (36)
"Nicely appointed. Super close to beach. Has coffee maker but no supplies, so be sure to bring filters, coffee, and cream/sugar. Good communication with owner when we had questions."
Cozy Bay Cottage private backyard blocks from beach!

Welcome to the Cool Change Beach Cottage, Canal front 4x4 area of Carova Beach.

10.0 out of 10, Exceptional, (2)
"Can’t say enough positives about our stay at Cool Change. House is perfect location on the canal… beautiful sunsets every night. Short walk or drive to the beach. The house has everything you could possibly want or need. The screened in porch is perfect to share meals or just enjoy the tranquility of the canal. So many cute touches throughout the house from furnishings to decorations.Working with Amber was easy and she was super attentive. No one in our group had any complaints. Perfect vacation...
Welcome to the Cool Change Beach Cottage, Canal front 4x4 area of Carova Beach.

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)

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 Beach Cottage - Walking distance to the Beach!!

9.8 out of 10, Exceptional, (71)
"Awesome house. great TVs. Beautiful kitchen and bathrooms. Plenty of amenities. Perfect location for us. Will definitely come back. "
Cozy Beach Cottage - Walking distance to the Beach!!

Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

9.0 out of 10, Wonderful, (30)
"We had a great time. The house needs a little cosmetic things done to the outside but the inside was beautiful. It is right on the beach and our kids loved going out to play in the sand."
Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

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

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

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

Charming Newport News Cottage < 1 Mi to Ocean!

8.2 out of 10, Very Good, (10)
"Was great for what I needed. Little trouble with the lock but host was great."
Charming Newport News Cottage < 1 Mi to Ocean!
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.
Don't see what you're looking for?
See all available properties in Chesapeake
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chesapeake

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1318)
"Very nice hotel on the beach "
The price is AEDĀ 327
AEDĀ 594 total
includes taxes & fees
15 May - 16 May
The Ocean Key Virginia Beach Resort

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very Good, (1324)
"Location is great close to beach nice places to eat nearby."
The price is AEDĀ 297
AEDĀ 560 total
includes taxes & fees
15 May - 16 May
The Atrium Resort, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very Good, (1047)
"very nice place"
The price is AEDĀ 331
AEDĀ 599 total
includes taxes & fees
15 May - 16 May
Ocean Sands Resort, Oceanfront, 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.