Cottage holiday rentals in Williamsburg

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Popular amenities for cottage rentals in Williamsburg

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 Willoughby Spit
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 Willoughby Spit
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.
Cottage in Williamsburg

Kings Creek Plantation - Williamsburg - Cottage

IriselRating, 5 stars72 months ago
This place is amazing.... We had an awesome family vacation!!
Guest favourite
Cottage in Willoughby Spit
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.
Superhost
Cottage in Foster
4.85 out of 5 average rating, 72 reviews

Old Log Cabin School House w/10 acres on the Bay

MichelleRating, 5 stars1 week ago
Great peace of history in a peaceful location. Kids thought it was coolest place ever to go kayaking, fishing, catching crabs, and relaxing inside playing chess and listening to some records. Richard was very accommodating with how far we had to travel and was able to help with a flexible check in time.

Pet-friendly cottage rentals

Top guest favourite
Cottage in Bayview
4.97 out of 5 average rating, 249 reviews

Villa Positano

RhondaRating, 5 stars5 days ago
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!!!
Top guest favourite
Cottage in Weems
4.99 out of 5 average rating, 115 reviews

The Crab Shack

TarynRating, 5 stars1 week ago
This was our 1st visit to The Crab Shack. All I can say is Wow, just Wow! This was the cleanest, nicest and cutest Airbnb that we have ever stayed at over the years! It was amazing! My husband and I traveled from Sarver, PA with our 2 Golden Retrievers to celebrate our 10 year Wedding Anniversary! We all had the best time ever! We spent most of the time here at the Shack just cooking on the grill and listening to music and the girls did a lot of swimming fetching for balls! Thank you Carlisle and Mary for making our 10 year Anniversary simply perfect! ❤️☀️😎🥂🍾🦀 We can’t wait to come back! ☺️
Guest favourite
Cottage in Deltaville
4.83 out of 5 average rating, 181 reviews

The Little House at Waveland

AshleyRating, 5 stars1 week ago
We had a great time at Diana’s place. The water access was awesome and we had lots of fun with the kayaks. We were able to walk through a wooded trail to a nearby restaurant which was so nice. The location felt private and naturally beautiful while being not far from grocery stores and restaurants. Diana’s neighborhood is beautiful and the space is charming and comfortable. Such a fun way to see the Chesapeake, we would love to come back!
Top guest favourite
Cottage in East Ocean View
4.98 out of 5 average rating, 254 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

KimberlyRating, 5 stars2 days ago
Great house. Perfect location easy access to the beach! Lovely front yard! Plenty of room and had absolutely everything we needed. Even a sweet goody bag with local items and a dog toy for our dog❤️ Hosts communicate very quickly!! Highly recommend!
Guest favourite
Cottage in Willoughby Spit
4.93 out of 5 average rating, 107 reviews

Comfy three bedroom cottage - easy beach access

MatthewRating, 5 stars1 week ago
Great place for a quick getaway! The beach is right across the road and wasn’t crowded at all during our stay. There’s plenty to do in the surrounding areas and we enjoyed attending the Harbor Fest!
Top guest favourite
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!!
Top guest favourite
Cottage in Ocean View
4.96 out of 5 average rating, 334 reviews

Lovely Ocean View Cottage

ClaireRating, 5 stars1 week ago
The cottage was in a nice quiet neighborhood, could walk the dog, it also has a fenced in yard. The home was exceptionally clean, it has all amenities needed, even a few extras, gas grill, beach chairs etc.. The bed was comfortable. Also enjoyed the water and snack basket that was left with a welcome note. Definitely recommend! Really felt like home! Short drive to restaurants and shops and a 2 minute drive to a cute little beach with lifeguards, restrooms and a free parking lot!
Superhost
Cottage in Cape Charles
4.78 out of 5 average rating, 113 reviews

Sea Salt Cottage: Tranquil Getaway 5 min to beach

GregRating, 5 stars1 month ago
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!

Private cottage rentals

Top guest favourite
Cottage in Cape Charles
4.99 out of 5 average rating, 73 reviews

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

ZachRating, 5 stars1 day 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!!
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.
Superhost
Cottage in White Stone
4.93 out of 5 average rating, 28 reviews

Renovated, Waterfront Cottage on the Rappahannock!

MarettaRating, 5 stars7 months ago
We had a great long weekend stay. The house was spacious and well appointed. We loved sitting outside under the stars and playing with the kids in the sunroom. Was such a nice touch to have kids toys at the house and lots of space to gather. We had one issue with the HVAC but each space had a window AC unit and the host was super helpful and responsive. Would 100% recommend and stay again.
Top guest favourite
Cottage in Willoughby Spit
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!
Top guest favourite
Cottage in Topping
5 out of 5 average rating, 33 reviews

Locklies Innlet, A unique waterfront experience!

CatherineRating, 5 stars3 weeks ago
My husband and I had an absolutely wonderful time and the home played a big part in this. I was so impressed with all the extras that I just never see in other homes. The house is so cozy and such a beautiful location. Just perfect for relaxation. We will definitely want to come back. Thank you Cornelia for opening up your home to us.
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 !!
Top guest favourite
Cottage in Gwynn
4.96 out of 5 average rating, 212 reviews

Mystic Seahorse Cottage & game room

MargieRating, 5 stars3 weeks ago
Mystic Is a quaint, clean and welcoming houae. All details from pictures to knick knacks create a complete theme. Instructions were easy and thoughtful. Communications were prompt and thorough. This home and its owners create a perfect sanctuary.
Guest favourite
Cottage in Gwynn
4.86 out of 5 average rating, 36 reviews

Sunset Haven

ConnieRating, 5 stars7 months ago
This is our second time staying at Sunset Haven— appropriately named. Gorgeous sunsets and weather was perfect. Great and considerate communication with Terri. House was pristine and had every thing you could need. We will be back! Thank you Terri!

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