
Cottage holiday rentals in Hampton Roads
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Top-rated cottage rentals in Hampton Roads
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Popular amenities for Hampton Roads 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.

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.

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 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!

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

Beach Cottage-Bay Views Loft on Beach & Veranda
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.

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 didn’t have to bring our own. We’d definitely love to come and stay again.
Pet-friendly cottage rentals

2 bedroom 1 bath Cozy Beachfront
Brian was a wonderful host, and the beach cottage was absolutely beautiful. It reminded me of my grandmother’s home, which made the experience even more special. My family and I were so happy staying there—it truly felt like a home away from home. We hope to return soon.

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!!

Villa Positano
We had an amazing time. The house was perfect for us. We really enjoyed the pool and short walk to the beach. We could hear the ocean from the master suite. The upstairs deck had view of the water. Everything about our stay was perfect. The area was nice and was quiet and peaceful. We will definitely go back and stay longer next year. Thank you!!!

Seaglass Cottage
Perfect stay for our weekend getaway. The cottage was so cute and so clean. Susan was so friendly and even had a welcome sign with my name on it! So many recommendations and such great hospitality. Great location! We walked everywhere! Highly recommend!!

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!

Sea Salt Cottage: Tranquil Getaway 5 min to beach
We stayed here for a little weekend getaway, and it was lovely. The space was comfortable and very quiet. We got great sleep and enjoyed watching the sunsets out back. Would recommend!

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 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.

Quaint 2 Bedroom Cottage in Chicks Beach
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.
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. I’m 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 didn’t 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.

“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 !!

At Sunset 2/Sandbridge Beach, VA
Andy was a wonderful host. She met us when we arrived and provided information that was helpful for our vacation. The communication was outstanding! The space and environment was soo peaceful and thoughtfully organized.

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 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!

Enchanted Holiday Cottage
This was our second time staying. The cottage is very clean and comfortable and convenient to local restaurants, stores, and attractions. Hosts are very responsive to any needs. Highly recommend!
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
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- Outlook Beach
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- Sarah Constant Beach Park
- Virginia Beach National Golf Club
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- Royal New Kent Golf Club
- Kiptopeke Beach
- Little Creek Beach
- Golden Horseshoe Golf Club
- Chrysler Museum of Art