
Cottage holiday 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
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.

Jul 12-19 $1155 3-bedroom Williamsburg
We loved our stay! The week flew by. Great location.

Corolla Light Resort | HotTub | 6BR ~ Indoor Pool
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!

Waterfront Gloucester Cottage w/ Private Boat Dock
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!

Beach Cottage - On Beach with Wrap Around Porch
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 canât 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 couldnât leave. The WiFi wasnât 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!

Beach Cottage-Bay Views Loft on Beach & Veranda
Enjoyed the stay. Comfy beds with wonderful cotton linens. Cute interior. Nice, quiet off season experience. Johnâs 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.

Kings Creek Plantation - Williamsburg - Cottage
This place is amazing.... We had an awesome family vacation!!

Poseidon - Beach Carriage House - 120 Years Old
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 didnât have to bring our own. Weâd definitely love to come and stay again.
Pet-friendly cottage rentals

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

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!

Saltwater Seaclusion- Corolla-Walk to Everything!
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! âď¸âď¸âď¸âď¸âď¸ Thank you Marcy!

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!

Dog friendly, large fenced yard! 1st Floor Bedroom
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 Josephâs 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. Thereâs also a wonderful fire pit in the backyard that would be perfect for sâmores while you wind down the day. The house even had things we might need for our dogs like water bowls and waste bags. Itâs a wonderful beach house for dog lovers or those looking to just kick back and enjoy some family time in cape Charles.

Quaint Beach Cottage in 4WD-OBX
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.

Quaint 2 Bedroom Cottage in Chicks Beach
This was my second stay at Kathyâs 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.

ManeStay Island Beach Cottage - Wild Horses Roam
This is our third time staying at Dianeâs place and it was wonderful as usual. Itâs always refreshing to experience the quiet atmosphere and peaceful surroundings. Great place to relax.
Private cottage rentals

Riverfront Oasis | Kayaks, Private Beach, & More
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. Iâm definitely going to book here again.

*Vintage Cottage on Creek Peaceful Private Sunsets
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 didnât seem to get very warm. It served our needs well and provided a quiet, peaceful experience.

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!

Beach Music Chesapeake Bay Getaway for all Seasons
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.

Carova Beach Crash Pad
Susanâs place was perfect and exactly as described. We had a wonderful stay and will definitely consider staying there again!

Adorable 2 BR Cottage in Swan Beach- 4WD required
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.

The Cottage at Church's Island
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!

Treetop Flyer OBX Beach Cottage
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 couldnât 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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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Currituck Beach Lighthouse
- Outlook Beach
- Jamestown Settlement
- Haven Beach
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Kiptopeke Beach
- Golden Horseshoe Golf Club