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

Horses-Views-Dog Friendly-4WD Area
Enjoyed every minute of our stay! The dogs loved the location and driving on the beach was a lot of fun. 2 stallions walked through the dunes directly off the porch. The house was cozy and all we needed!

Private Pool | Oceanview | Hot Tub | 6 BedRoom
Ashley was a GREAT host, very responsive and a caring host. Provided high chair requested, allowed an earlier check-in to help accomodate special needs child and was very concern when access lock was having problems and responsive. Problem was pribably our mittle hands tiuching all the numbers. Pool was extremely clean and as described in pictures and notes. Had family of 17, 8 adults and 9 kids ranging in age from newborn to 13. Bedrooms were good size to accomodate and all suites having own bathroom was wonderful for 5 families.

Kasita Barceló | Pool, HotTub, Near Beach, Slps 10
We loved our stay at Kasita Barceló. The house was beautiful, clean and big enough to comfortably fit 10 of us. The house was fully stocked with all basic necessities which really helped us at meal times. The host was very accommodating and super helpful anytime we had a question. We will definitely be 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.

Waterfront Gloucester Cottage w/ Private Boat Dock
This home was exactly what we needed - a beautiful, relaxing space with wonderful views. Every home along the private road is lovely - the azaleas in bloom during our April stay were stunning! The house itself was clean and had every amenity. The outdoor space was fantastic! We enjoyed our time sitting and rocking and looking at the river. We drove in to Williamsburg twice. It was a bit of a drive, but was worth it. Gloucester is a cute town and we did a little shopping & eating. Don’t hesitate to book this home!

Beach Cottage - On Beach with Wrap Around Porch
Really enjoyed our stay. We will definitely be back. Airbnb was central and just a stone throw to the beach. We had a toddler and it was very safe and comfortable. We brought a travel crib but they did have one actually in the closet for us which was excellent, coffee was great also. Went for dinner at the Willoughby fish house which was 5 minutes away and really enjoyed it! I absolutely recommend this stay and I imagine we will book again.

Beach Cottage-Bay Views Loft on Beach & Veranda
Everything was wonderful, easy to get in, and our host John was very helpful and friendly. Hotub was clean no trash in the yards felt just like home. comfortable beds the walkway to the beach was very private enjoyed that as well. Overall our stay was amazing and would love to be able to stay there again. We had so much fun <3 provided us with some detergent to wash clothes I thought that was thoughtful.
Pet-friendly cottage rentals

The Ladybug - arcade, dog-friendly, firepit, & EV
To say this house was a dream come true would be an understatement. From the moment we drove up the long driveway and laid eyes on the picturesque setting of the red house nestled in the woods, we fell in love. My 17-year old daughter walked in and said the pictures online did it no justice and she is exactly right. The house was immaculate, with every feature you could possibly imagine. The technology throughout was unbelievable. Google Home in EVERY room. TVs with surround sound. A game room that kept us busy for hours. A karaoke machine. It was a much needed getaway. Our dogs were in heaven with the acres of land to explore on walks. I have never felt so relaxed. I just can’t say enough. I love the city of Cape Charles but honestly did not want to leave this house. The host, Dave, was so great with communicating, even before we arrived. We will definitely plan another visit here! I would say the only downside was getting carpel tunnel trying to beat high scores in the arcade room. ?

Beachfront Cottage
My husband and I spent a week at the beach cottage. The location is unbeatable, just steps to the beach. If you are not fond of the sand, you can sit in the porch and enjoy the view. You will not want to leave! The house was clean and exactly as pictured. Cecilio and his wife answered promptly all of my questions about places to eat and things to do. If you enjoy fishing, the Ocean View pier (longest in the State of Virginia) is just a half a mile walk from the house, or a short drive. You can rent fishing poles, buy bait, and feel like a local. You can also get some crab traps and get blue crabs. The pier has a restaurant with a nice view and a full bar. The beach right outside the house feels private. It is the perfect place to relax and enjoy a good book. If you like water activities, the cottage has plenty of beach gear, including paddle boarding, and kayaks. We wanted to relax and reconnect, and this place was the perfect spot for us. Highly recommended.

Saltwater Seaclusion- Corolla-Walk to Everything!
Great place for a quiet, beach weekend! The apartment was bright, cheery, beach and clean. More than fully equipped - I can’t think of anything we could possibly ask for that wasn’t provided, including a well-stocked coffee bar and ice machine. Outdoor shower and rinse area with bicycles just a 5 minute walk to the beach. Great little bar/ food shack just two minutes away in the complex. Marcy was always proactive and responsive - a great host! We looking forward to coming back!

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!

Dog friendly, large fenced yard! 1st Floor Bedroom
Our stay with family was a blast! We had beautiful weather for our stay and the front porch was our favorite for hanging out! And the fireplace was nice and cozy on the cooler mornings. The location is so convenient for walking downtown to restaurants and shops. Thanks for sharing your little piece of paradise!

ManeStay Island Beach Cottage - Wild Horses Roam
Honestly, this is easily one of the best airbnb experiences we have ever had! Diane was so helpful and communicative from the start. The location cannot be beat and the house was lovely! It was bright, airy, and clean and completely matched the description. We saw so many wild horses and were able to relax a ton. It was exactly what we needed and will absolutely be saving Diane's home for future stays!

Waterlily Waterside Cottage with Game Room
We absolutely loved our stay at Ritta’s place! It was close to the event we were staying at, any questions I had she answered fast! The house was beautiful as well as the location! She had great recommendations. We felt right at home and my son enjoyed every minute of his birthday weekend! We can’t wait to come again one day!

Epic Sunsets | Waterfront Cottage | Pet Friendly
Badria and Jay were exceptional hosts. They were extra communicative even when I had a very late arrival and checked in periodically to see how we were doing. We felt at home as soon as we got there. The place is gorgeous and perfectly located for amazing views at home and short distance to the beach. The cottage is well stocked and organized so it was easy to find everything we needed. I would highly recommend staying at Sea La Vie and being hosted by Badria and Jay!
Private cottage rentals

Riverfront Oasis | Kayaks, Private Beach, & More
We will definitely be coming back for a longer stay!! We loved the location (I mean bald eagles swooping over the water at sunrise kind of love) and our daughter loved exploring the beach with the shells. The house was just so thoughtfully stocked from the extra syrup to the little fire pit for the back. We felt right at home 🩷💚🩷💚

Cozy Cottage Smiley Palms
Beautiful home, next to a peaceful nature preserve. Thoughtful touches throughout the home to make your stay easier. Such a great retreat for our family and only about 15-20 minutes from 64, the Colliseum area!

“Magnolia Cottage” on the River
Really great and peaceful experience, nice get away for couples!

Vintage Beach Cottage by the Chesapeake Bay
Beautiful beach property, furnished in style, has all necessary things from kitchen appliances to kids entertainment. Felt right at home.

At Sunset 2/Sandbridge Beach, VA
This was a great place. Clean, well equipped, comfortable and private. Andria was an excellent host and provided over and above. She met me at check in and explained everything. Also recommended restaurants. She was very accommodating with check in and check out. Highly recommend and I will go back again.

The Little Jewel
Our first visit to Cape Charles and we loved it. K’s house is in a lovely residential area, but very close to shops and restaurants and a 10 minute walk to a beautiful beach area. The house is simple but comfortable and has everything you need (no high chair or pack & play, but we brought our own). We loved sitting on the porch.

The Seaglass Cottage by the Chesapeake Bay
We were looking for a place where we could host our local family a few hours each day. It worked perfectly. The kids loved it...the foozball table, upstairs room where they could read books, large dining table with benches, etc, We loved enjoying our mornings sitting in the Mud Room, which we called the Sun Room. The neighbors really watch out for this property, thinking that at one point, we may have driven away leaving the front doors open. It is a safe neighborhood. There is a bar on the other side of the fence, but it was never an issue. And we enjoyed walking the neighborhood, and having Date Night at a different restaurant which offered live music across the street. Super convenient to get to the grocery store, airport, etc. We plan to return on our next visit! Thanks....

The Cottage at Church's Island
The house was newly remodeled and clean with a fantastic view of Currituck Sound. We felt safely isolated from the world. It felt very private even though there were other cottages near by. The kitchen was fully stocked with not only dishes, etc., but spices, coffee, and other necessities that we may have forgotten to bring. There is a lovely porch in the back with a beautiful view of the Sound. Very peaceful, safe, and comfortable.
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- Virginia Beach Oceanfront
- Carova Beach
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- Busch Gardens Williamsburg
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