
Cottage holiday rentals in Chesapeake
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Top-rated cottage rentals in Chesapeake
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Popular amenities for cottage rentals in Chesapeake
Cottage rentals with a hot tub

Horses-Views-Dog Friendly-4WD Area
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.

Kasita Barceló | Pool, HotTub, Near Beach, Slps 10
Nice clean house to stay at

1-Min walk to Beach! Ocean Views, Hot Tub
Stayed here for Memprial Weekend. Wasn't sure on how busy it would be, but turned out great. This house is literally just a quick minute walk to a private beach. Made watching the sunrise so easy to do. The house feels spread out, which is perfect for multiple families. The kitchen was well stocked with all the necessities. The AC cools the entire house, much needed on hot days. The beds were also super comfortable. Hot tub was such a nice way to end the day. James was super quick on answering any questions that popped up during my stay. This entire community is really nice with lots of places to walk the dog. Was hard to leave, can't wait to come back

Beautiful Obx Home W. Pristine Views
We had a wonderful time and enjoyed the house and ample space for our large group. House exceeded my expectations. Short walk to the beach. House had plenty of beach toys for the kiddos and beach chairs. Had to reach out for check-in instructions the day of check-in, and the initial code provided did not work, but host was responsive and got us in quickly.

Semi Oceanfront 5 bedroom dog friendly cottage
This was our second stay, and we remain very happy with this rental. The location is ideal, directly across the street from a beach access walkway and with nice partial ocean views from the deck/upper floor. The house is easy to find and enter with a key code unique to each visitor. The house is clean and well appointed, and includes basics/starters of basics (e g., dish soap, dishwasher soap, bathroom sink and shower soap, laundry soap, paper towels, TP), which is very helpful. Other distinguishing features, include: - Comes with sheets and towels - Has a lift, which is very convenient for getting luggage, groceries, etc. to the third floor - Friday turnover saves you from the crazy terrific that can build up during Saturday and Sunday rental turnovers. Debbye gives clear and complete instructions and is appropriately communicative and available. She even left some welcome gifts (e.g., chocolates, wine), which were appreciated. We would happily rent this house again.

The Cottage @ Captain Genes - Secluded Waterfront
Our stay in this home was such a treat! We enjoyed utilizing the kayaks to boat around in Chesapeake Bay. The hot tub was an absolute delight, perfect for evening stargazing, saw lots of shooting stars, and could see the water of the bay from the hot tub. We also enjoyed doing November cold plunges from the hot tub to the pool. While the living room is not expansive, it fit our needs for family game & movie nights. The bed linens were so comfortable, and Lori was beautifully responsive & friendly when we would reach out with a question. We also enjoyed the nearby Sandy beaches.

Seahorse Shanty
We had an excellent stay as a group of 8 adults. The home offered great access to a semi-private beach, just a short 5-minute walk away. Kendra was proactive and clear with her instructions, making check-in and our overall experience smooth and stress-free. The neighborhood was very quiet, providing a relaxing atmosphere, yet still conveniently located with shops just a short drive away. After long days at the beach, the hot tub was a refreshing bonus. This home is perfect for both families and adult groups—highly recommended!

Coastal Cottage, heated pool, resort community
Place was really cute and accommodated my family well. Place was clean and easy to find. Pool was nice as well, pool toys available for children. Pleasant stay look forward to coming back
Pet-friendly cottage rentals

Key Lime Cottage - Your Beachside Retreat
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!

Lighthouse Views, Beach Parking Pass, Pets Welcome
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!

Saltwater Seaclusion- Corolla-Walk to Everything!
We really enjoyed Marcy's place at Corolla. It was a great location with easy access to the beach. The house was well furnished, and it made our beach trip easy and enjoyable.

Sea Salt Cottage: Tranquil Getaway 5 min to beach
This was the perfect find for exactly what we needed- a peaceful and quiet few days to escape our hectic everyday. The home was cozy and lovely and exactly as described. Cape Charles is a gem of a town and we look forward to coming back!

Dog friendly, large fenced yard! 1st Floor Bedroom
Isn't it wonderful when things not only work out but exceed expectations?! This sweet house is homey and comfortable. Erika has thought of everything! The entire house is fully equipped and stocked with essentials. The beds with quality linens & pillows are luxurious. The completely fenced large back yard is perfect for doggies. The location is walkable to the beach, shops & restaurants. A quaint park is nearby as well. Tasty snacks upon arrival were appreciated! There's really no need to look further for your Cape Charles getaway!

Quaint Beach Cottage in 4WD-OBX
We had a great stay at Kimberlys place. She was extremely awesome at communicating throughout the process. The house met and exceeded all of our expectations. Would highly recommend!

ManeStay Island Beach Cottage - Wild Horses Roam
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.

Waterlily Waterside Cottage with Game Room
We loved our stay here! Gorgeous property with an amazing view. The place looked exactly like the photos and was very clean. They had lots of thoughtful additions to the home (usb chargers next to every bed, extra fans, etc). We had such a great time (the dogs loved it too!). Highly recommend, can’t wait to come again!
Private cottage rentals

*Vintage Cottage on Creek Peaceful Private Sunsets
A truly delightful stay at a cozy home with beautiful views!!! Leslie was an incredibly communicative and thoughtful host. She ensured we had everything we needed for a comfortable and memorable stay.

Life on a Sandbar right on Chesapeake Bay
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!

Cozy Cottage A, Steps to the Beach!
This was the perfect home for our family trip to Virginia Beach! From check-in to check-out it was an extremely easy/smoothe process with great response from our host! We loved the coziness of the home. The beds were comfortable, and the couches comfy. The backyard was perfect for hanging out and bbq'ing! The best part for us - all the sand toys, beach chairs, umbrella and wagon to haul everything to the beach! We loved the close proximity to the beach (especially with little kids!) Highly recommend this home and will be booking again in the future!

“Magnolia Cottage” on the River
We can’t express how much we enjoyed our stay . It was more than we expected ! Rose was so accommodating . And she makes the best Belgium waffle with fresh organic fruit and granola we have ever had . It’s worth every penny !! And the coffee was approved by my husband that’s a Veteran that loves his coffee . Thank you Rose for making our two short days there a great memory . And I’m going to get that outside shower I’ve been wanting for years !!

The Crew's Quarters: Steps from the Bay
Caryn’s home was perfect for our needs. She was very responsive to our question and provided valuable information about the area.

Vintage Beach Cottage by the Chesapeake Bay
Great clean place. Only a minutes walk to the beach. Neighborhood was very nice and quiet. Would definitely recommend to anyone looking for a place to stay in VA Beach.

Adorable 2 BR Cottage in Swan Beach- 4WD required
My first trip to outer banks since I was a child some 50 years ago. Place was just as described, and Joseph seems to be a first class guy. Very responsive to messages, usually in minutes. Place was well equipped (beach chairs, coolers, surfing / snorkeling gear, etc..) You could basically show up and only need to buy food & your beverage of choice. Our place was at the smaller end of the scale, which was exactly what we wanted. Well worth the price, and when we go back, I’ll certainly be reaching out to Joseph. Also, regarding the horses, not a single day went by without us seeing them, especially driving along the beach at night. I’m convinced we saw them more than the folks on the paid tours. One word of advice: Bring a capable 4 wheel drive vehicle! You’ll see nothing but sand & water for miles once you leave the blacktop.

The Cottage at Church's Island
truly the most beautiful, stocked, homey airbnb I've ever stayed in. we were shocked by the amount of items that were on hand; plenty of towels, a fully stocked kitchen, blown up floats, plenty of cleaning supplies. The view is absolutely beautiful and the water was waist deep which was PERFECT for floating on a nice day. The pictures truly dont do the place justice. Its bigger than we expected and was super clean. we were truly blown away. if you're looking for a private, peaceful stay that's only 25 minutes outside of Kitty Hawk, I highly reccomend.
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