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Cottage holiday rentals in Hampton Roads

Find and book unique cottages on Airbnb

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Popular amenities for Hampton Roads cottage rentals

Cottage rentals with a hot tub

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.
Guest favourite
Cottage in Chesapeake
4.95 out of 5 average rating, 132 reviews

The Cottage @ Captain Genes - Secluded Waterfront

LindseyRating, 5 stars6 months ago
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.
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 Norfolk
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 Williamsburg

Kings Creek Plantation - Williamsburg - Cottage

IriselRating, 5 stars72 months ago
This place is amazing.... We had an awesome family vacation!!
Cottage in Norfolk
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.
Guest favourite
Cottage in Norfolk
4.94 out of 5 average rating, 169 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.
Cottage in Cape Charles

Bungalow w/ Large Yard: 8 Mi to Cape Charles Beach

KierstinRating, 5 stars1 month ago
We absolutely loved staying here! It was the perfect distance from Cape Charles where we visited during the day. It was the perfect little getaway!

Pet-friendly cottage rentals

Cottage in Norfolk
4.73 out of 5 average rating, 11 reviews

2 bedroom 1 bath Cozy Beachfront

RhondaRating, 5 stars2 weeks ago
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.
Superhost
Cottage in Cape Charles
4.99 out of 5 average rating, 73 reviews

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

ZachRating, 5 stars2 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!!
Cottage in Cape Charles
5 out of 5 average rating, 8 reviews

Pristine cottage 3 bdrm, 2.5 bath, HD

KateRating, 5 stars1 week ago
If we would give more than 5 stars we would! This place was absolutely perfect for our family of 5 and our dog. The house was even cuter than the pictures and really spacious. Plenty of comfy seating for everyone. Everything was spotlessly clean and felt like we were the first people who ever stayed there! The location was super convenient for the beach and downtown. The owners clearly have thought of everything - the house was stocked with so many useful items for a perfect cape charles vacation - beach chairs, umbrellas, sand toys, stand up paddleboards, cooler and ice packs, beach towels, rafts, boogie board - made packing so much lighter knowing we had all of those things waiting for us. The outdoor spaces were also great - a comfy and shady front porch, a nice deck and fire pit out back, and an amazing outdoor shower! I can't say enough great things about this house!
Cottage in Virginia Beach
4.62 out of 5 average rating, 109 reviews

Cottage in the Heart of Virginia Beach

JohnRating, 5 stars3 weeks ago
Great location, private, and walkable to all points of interest. Craig and April were very friendly and fast to respond. Would definitely book again in future.
Cottage in Williamsburg
4.7 out of 5 average rating, 37 reviews

Cottage in Williamsburg / Busch Gardens

SamRating, 5 stars2 months ago
Charming cottage at a family-owned, lovingly-crafted campground. It suited our needs perfectly. We traveled with our dog and all the other dogs on site were all on leashes and well-behaved. The staff was very helpful and we would definitely stay here again!
Superhost
Cottage in Virginia Beach
4.95 out of 5 average rating, 394 reviews

Seaglass Cottage

NicoleRating, 5 stars3 weeks ago
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!!
Superhost
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!
Superhost
Cottage in Cape Charles
5 out of 5 average rating, 70 reviews

Dog friendly, large fenced yard! 1st Floor Bedroom

GenevieveRating, 5 stars3 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.

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, 68 reviews

*Vintage Cottage on Creek Peaceful Private Sunsets

AshaRating, 5 stars3 weeks ago
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.
Top Guest favourite
Cottage in Norfolk
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 Virginia Beach
4.82 out of 5 average rating, 50 reviews

Cozy Cottage A, Steps to the Beach!

SherryRating, 5 stars2 weeks ago
Very enjoyable location and so close to beach but far enough away from boardwalk. House was beautifully decorated and spacious
Guest favourite
Cottage in Surry
4.91 out of 5 average rating, 68 reviews

“Magnolia Cottage” on the River

VeronicaRating, 5 stars3 weeks ago
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 !!
Guest favourite
Cottage in Cape Charles
4.93 out of 5 average rating, 27 reviews

The Crew's Quarters: Steps from the Bay

SueRating, 5 stars2 weeks ago
Caryn’s home was perfect for our needs. She was very responsive to our question and provided valuable information about the area.
Superhost
Cottage in Virginia Beach
4.87 out of 5 average rating, 79 reviews

Vintage Beach Cottage by the Chesapeake Bay

AndiRating, 5 stars1 month ago
Great little beach house right by the ocean. We loved the local restaurants and walking around the neighborhood.

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