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Cottage holiday rentals in Chesapeake

Find and book unique cottages on Airbnb

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Popular amenities for Chesapeake cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Carova Beach
4.89 out of 5 average rating, 150 reviews

Horses-Views-Dog Friendly-4WD Area

RamonaRating, 5 stars3 weeks ago
The place was perfect. Very well stocked and pet friendly. We saw horses daily by the rental. Very easy access to the beach. Only thing it needs is a sign out by the entrance of the driveway with house #. We came in at night during a storm and it took us a few minutes to find the drive. I definitely recommend.
Cottage in Williamsburg

Jul 12-19 $1155 3-bedroom Williamsburg

AndreaRating, 5 stars11 months ago
We loved our stay! The week flew by. Great location.
Superhost
Cottage in Corolla

Corolla Light Resort | HotTub | 6BR ~ Indoor Pool

SusanRating, 5 stars21 months ago
The house is walkable to restaurants, coffee shops, beach and pool area. I was concerned from looking at the map, but everything was very convenient for our whole family. The house was comfortable, clean and well supplied with good quality linens, kitchen items and beach chairs. The only thing missing for a few in our group, was basic cable for football game viewing on cloudy days. Ashley was very communicative. We would stay here again!
Guest favourite
Cottage in Gloucester
4.95 out of 5 average rating, 20 reviews

Waterfront Gloucester Cottage w/ Private Boat Dock

RebeccaRating, 5 stars3 weeks ago
We had a great time staying here! Clean, modern, fully stocked home just as described in the listing and photos. The sunsets over the water are indescribable. Relaxing hot tub, wonderful outdoor space, lovely campfires, and comfortable bed and bath rooms made our trip stress free and extremely enjoyable. We barely left the property - we felt right at home. Our point of contact host, Ana, was very responsive and communicative. Would definitely recommend! Look forward to booking again in the future! Thank you for a vibey holiday weekend!
Cottage in Willoughby Spit
4.8 out of 5 average rating, 143 reviews

Beach Cottage - On Beach with Wrap Around Porch

AmberRating, 5 stars2 weeks ago
We loved staying here! The location was great and it was roomy. Super close to the beach, great outdoor amenities, and a nice porch. Host was quick to respond. We pretty much had the beach to ourselves, it was like a private getaway! There were a few cons: very noisy upstairs guests (I know this can’t be helped, but it was bad,) the parking spaces were EXTREMELY tight and one of the guests kept parking in 2 spaces instead of one. There was a narrow gravel driveway offered, but if someone parked behind you then you couldn’t leave. The WiFi wasn’t strong enough to watch tv, we had to keep pausing it so it would load a little. All in all it was a great deal and would definitely stay here again!
Cottage in Willoughby Spit
4.79 out of 5 average rating, 119 reviews

Beach Cottage-Bay Views Loft on Beach & Veranda

MarthaRating, 5 stars4 months ago
Enjoyed the stay. Comfy beds with wonderful cotton linens. Cute interior. Nice, quiet off season experience. John’s recommendations for smaller local favorite restaurants were good choices. Nearby recreation centers offer day passes and lots of indoor activities for cold or rainy days. Just right for our family trip. Highly recommend.
Cottage in Williamsburg

Kings Creek Plantation - Williamsburg - Cottage

IriselRating, 5 stars72 months ago
This place is amazing.... We had an awesome family vacation!!
Guest favourite
Cottage in Willoughby Spit
4.92 out of 5 average rating, 170 reviews

Poseidon - Beach Carriage House - 120 Years Old

JessicaRating, 5 stars2 weeks ago
We enjoyed our stay at Poseidon. The carriage house was perfect for us, and had everything we needed for our vacation. We appreciated having the chairs and umbrellas so we didn’t have to bring our own. We’d definitely love to come and stay again.

Pet-friendly cottage rentals

Top Guest favourite
Cottage in Cape Charles
4.99 out of 5 average rating, 73 reviews

The Ladybug - arcade, dog-friendly, firepit, & EV

ZachRating, 5 stars4 days ago
Dave & Anjeli have truly done a wonderful job with this Airbnb. Airbnbs often don't live up to their marketing but I think this is the first one I've encountered that greatly exceeded even our wildest expectations. There's something for everyone whether you're into gaming, music, cooking, the outdoors, or want easy access to town. The house was spotless, fully outfitted, effortless to check in and out, and Dave was perfectly communicative, always available when needed and on top of anything that came up during our stay but never felt overbearing in any way. This was the best experience I've ever had with an Airbnb and we would be happy to stay here again. A word to the wise- the Ladybug is surrounded by a nature preserve so it was buggy with both natural pollinators but also mosquitos and ticks which should come as no surprise given the timing of our stay. Make sure your pets are up to date on their tick preventatives and don't forget your personal pest preventatives. Thanks again!!
Top Guest favourite
Cottage in Cape Charles
5 out of 5 average rating, 23 reviews

Key Lime Cottage - Your Beachside Retreat

JessicaRating, 5 stars9 months ago
Such a great location - just a short walk from the beach. Front porch is a great place in the mornings and evenings. The dining room and living room fit our group well and we squeezed in the bedrooms (4 couples + 6 kids all 3 and under) but it was perfect since we spent most time outside anyways! Adam was super helpful and quick to respond when we needed a few items. Would definitely visit again!
Top Guest favourite
Cottage in Corolla
4.97 out of 5 average rating, 75 reviews

Saltwater Seaclusion- Corolla-Walk to Everything!

StephanieRating, 5 stars6 days ago
Our first awesome trip to OBX and we are so happy we booked here! This cottage is a true gem - spacious, comfortable, clean and beautiful. Location is wonderful and Marcy is a great host. We absolutely loved our stay and highly recommend. 5 stars! ⭐️⭐️⭐️⭐️⭐️ Thank you Marcy!
Top Guest favourite
Cottage in Corolla
5 out of 5 average rating, 12 reviews

Lighthouse Views, Beach Parking Pass, Pets Welcome

JaimeRating, 5 stars2 months ago
Jean-Paul's place was exactly as described but even better. Very clean and had everything for us to feel like we were at home. We will 100% go back to Salty Kisses when we go back to Corolla!
Top Guest favourite
Cottage in Cape Charles
5 out of 5 average rating, 70 reviews

Dog friendly, large fenced yard! 1st Floor Bedroom

GenevieveRating, 5 stars5 days ago
We were invited to join our family in cape Charles but wanted to find a place that would allow us to bring our two dogs. I was absolutely thrilled to find Erika and Joseph’s home, it had a HUGE fenced yard and an entire downstairs that allowed dogs. The upstairs is absolutely adorable with three more bedrooms! We were close to an adorable bakery, an equally great ice cream place, and only short stroll to the beach. Our entire family came over for coffee and we all enjoyed hanging on the front porch chatting. There’s also a wonderful fire pit in the backyard that would be perfect for s’mores while you wind down the day. The house even had things we might need for our dogs like water bowls and waste bags. It’s a wonderful beach house for dog lovers or those looking to just kick back and enjoy some family time in cape Charles.
Superhost
Cottage in Carova Beach
4.88 out of 5 average rating, 192 reviews

Quaint Beach Cottage in 4WD-OBX

JohnRating, 5 stars5 days ago
absolutely loved staying here once again. we had a blast seeing the horses, driving the seashore, and fishing the beaches. Definitely plan to come back again when we get the chance.
Guest favourite
Cottage in Chic's Beach
4.79 out of 5 average rating, 144 reviews

Quaint 2 Bedroom Cottage in Chicks Beach

KathyRating, 5 stars8 months ago
This was my second stay at Kathy’s and it was great. The location is perfect. Within easy walking distance to the beach, restaurants and a local brewery. And the fenced in yard was perfect for my pups.
Top Guest favourite
Cottage in Carova Beach
4.98 out of 5 average rating, 93 reviews

ManeStay Island Beach Cottage - Wild Horses Roam

BlakeRating, 5 stars3 weeks ago
This is our third time staying at Diane’s place and it was wonderful as usual. It’s always refreshing to experience the quiet atmosphere and peaceful surroundings. Great place to relax.

Private cottage rentals

Top Guest favourite
Cottage in Surry
4.96 out of 5 average rating, 50 reviews

Riverfront Oasis | Kayaks, Private Beach, & More

PaulRating, 5 stars1 month ago
This place was just amazing. The views of James River, and even the Jamestown settlement across the river (using binoculars) was just mind-blowing! Kevin and Jamie left a wide variety of amenities that were extremely thoughtful and useful, to include hygiene products, charging cords (which was a life saver because for literally the first time ever, I forgot my phone and iPad cords), coffee, and even a margarita kit! The cottage is so cozy, and was very clean. I’m definitely going to book here again.
Guest favourite
Cottage in Norfolk
4.81 out of 5 average rating, 69 reviews

*Vintage Cottage on Creek Peaceful Private Sunsets

CharleneRating, 5 stars1 week ago
The location was so beautiful with a lovely creek to view through the main living area. Beds were comfortable. The house temperature was a bit uncomfortable in the late evening. The rooms and home matched the pictures so were quite nice. The second bathroom was a bit rustic with a shower that didn’t seem to get very warm. It served our needs well and provided a quiet, peaceful experience.
Top Guest favourite
Cottage in Willoughby Spit
4.98 out of 5 average rating, 85 reviews

Life on a Sandbar right on Chesapeake Bay

CatherineRating, 5 stars6 months ago
The cottage was perfect for us and had everything that we needed! Jimmy was an awesome host and even shared that there was a pod of dolphins in the vicinity of the cottage! We had an amazing time!
Superhost
Cottage in Port Haywood
4.67 out of 5 average rating, 3 reviews

Beach Music Chesapeake Bay Getaway for all Seasons

AnnaRating, 5 stars10 months ago
Our stay at this property was truly an amazing getaway. The breathtaking views and stunning sunrises from the porch were a daily delight. The home is exactly as described and absolutely beautiful. We felt like we were at home. Each room is uniquely decorated. The doors opening up from the upstairs living room to the porch outside with a comfortable couch was so wonderful. We enjoyed the quietness Beach Music offered. We look forward to coming back soon one day.
Guest favourite
Cottage in Carova Beach
5 out of 5 average rating, 6 reviews

Carova Beach Crash Pad

ConnieRating, 5 stars9 months ago
Susan’s place was perfect and exactly as described. We had a wonderful stay and will definitely consider staying there again!
Guest favourite
Cottage in Carova Beach
4.92 out of 5 average rating, 26 reviews

Adorable 2 BR Cottage in Swan Beach- 4WD required

BrandiRating, 5 stars5 days ago
Our family of 4 really enjoyed our stay to Kokomo! It was just the right size with all the things you need. Our host was extremely hospitable and flexible. The house was very clean and the extra beach amenities was a plus! The location is wonderful and very fun with a Jeep! Town is not far away with great restaurants, shopping, and putt putt.
Top Guest favourite
Cottage in Coinjock
5 out of 5 average rating, 82 reviews

The Cottage at Church's Island

CourtneyRating, 5 stars1 week ago
This place was perfect for us for the week we stayed. It was close to Virginia Beach, we spent a day driving down the Outer Banks and doing things there and only a couple of hours from Jamestown/Williamsburg. The house was clean, had everything we needed for the week and the layout of the house was perfect. We enjoyed it very much!
Superhost
Cottage in Carova Beach
4.92 out of 5 average rating, 12 reviews

Treetop Flyer OBX Beach Cottage

MarcRating, 5 stars10 months ago
This house was everything we could have asked for. From arriving and having a horse friend right in the yard to driving the truck to the beach to spend the day, It couldn’t have been better. Marshall and Heather were extremely responsive and helpful with anything we need. We would definitely come back to enjoy this place again!

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