
Cottage holiday rentals in Williamsburg
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Top-rated cottage rentals in Williamsburg
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Popular amenities for cottage rentals in Williamsburg
Cottage rentals with a hot tub

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
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.

Poseidon - Beach Carriage House - 120 Years Old
Cozy and peaceful spot right by the beach. John was very welcoming and proactive in making sure the property was always well-maintained. We enjoyed our stay!

Old Log Cabin School House w/10 acres on the Bay
This old log cabin school house, this was one of the most amazing experiences our family has ever had in an Airbnb. The history in this home is something like I’ve never witnessed before in my life. You can feel the love that has been poured into this unique stay. It felt like home with endless bonuses found throughout the home, carriage house and property. Richard was an incredible host and this was by far the most personable experience we have ever had in all our years using Airbnb. You can feel the peacefulness this place offers from the moment you turn onto the driveway. The sunsets are breathtaking and we saw deer, turkey and a ton of other wildlife daily. One night right after sunset my husband caught a 24” speckled trout! Our four children, ages 12, 9, 4 and 1, all had a blast. We brought a baby gate for the living room/kitchen doorways and it was perfect! Downtown Mathews is adorable and we loved the visitor center. Definitely check this place out if you have the opportunity ?

3 BR Bay Home w Private Dock & all the Amenities
Our trip to The Half Shell Haven was great! The place was clean, extremely well stocked, and included many extras! We had crazy weather the first two days, but we had plenty to do at the house. My boys loved being on the water and the game room and my daughter loved the hot tub and bicycling. My daughters service dog enjoyed a nice reprieve and seemed so happy. We had a great time, and were honestly sad to go! If we find ourselves back up in Virginia we will definitely stay here! Thank you for the care and attention to detail to ensure a great trip!
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. ?

Villa Positano
💯 your money worth and the interaction with Roger was amazing .good location good fishing right of tha beach . safe and clean environment and gorgeous views

The Crab Shack
There is nothing more serene than waking up in the ‘crab shack’ with the sunrise. What a comfortable and scenic spot. Even our dog, Juno, loved it! Took a sunset sail to celebrate a birthday and got front pier service! Our host, Carlisle, was extremely attentive and kind with any needs we had or hadn’t thought of. Wish we had booked longer. We hope to return very soon!!

Comfy three bedroom cottage - easy beach access
We loved our stay at this amazing cottage! it felt like home, with every amenity possible and the walk to the awesome beach to the calm waters with beautiful sunrises, and dolphins passing by was awesome! We highly recommend this cottage and will come again next time!! Thank you so much!! ⭐️⭐️⭐️⭐️⭐️ Janet & Jerry from Michigan

"Bee Haven" Cottage Retreat
My parents and I stayed here for four days. It was the perfect peaceful getaway for us. The place was really cute, two bedrooms with queen size beds, a large bathroom, and the cutest kitchen-living room area. Gloucester is a sweet town to hang out in, and the host gave some great recommendations for local places to check out. Wonderful place, we will be coming back!!

Seaglass Cottage
We came here for a quick few nights and it was absolutely perfect. Susan was a great host. It was in a great location and there was lots in walking distance to do! We had a great time and would definitely come back and stay here again.

Cottage on Prentice Creek
I cannot find the words to express our families stay. When I say this was the best stay at an ABNB we have had thus far it was. The outside itself from the landscaping to the scenery was breathtaking. Checking in was a breeze. Once inside pictures cannot begin to show the beauty of this property. The hosts have really thought through a guest experience. They went over and beyond hosts duties adding extreme attention to details. Anything and everything you may need or want for your stay was there. Even with all the extra amenities and the beauty of the home our family instantly felt at home. We loved our stay so much we have already booked our next stay.

Lovely Ocean View Cottage
We had a wonderful stay with our puppy! Chuck was very thoughtful and welcoming with the many amenities available. We felt right at home and it's so close to restaurants and the water. Looking forward to our next visit!
Private cottage rentals

Peaceful Haven: nature & charming town
Wonderful place in a very nice town. We had the best time trying different restaurants and relaxing around the cottage. Gita was super helpful and friendly, giving us plenty of recommendations. We will absolutely be back!

Unique & bright two-bedroom waterfront cottage
We loved staying at this beautiful and peaceful house! The house cozy and we felt right at home! It even snowed when we stayed in Delaville! The sunset was gorgeous and it even more amazing with a layer of snow! Would definitely love to come visit again in the summer! Thanks for a lovely weekend!

Private Beach Access at The OV Beach House
Madeline & Michael’s place is great 👍 They’ve recently renovated everything inside and there was even more space than we expected. We thoroughly enjoyed the views, the back yard of sand, small path through the sand dune and access to the beach. Communication was great leading up to and throughout our stay. Thanks again for the hospitality!

“Magnolia Cottage” on the River
Absolutely beautiful and whimsical! I loved the gorgeous flowers and stunning views all around. The entire place felt so peaceful and relaxing—it was exactly what we needed. We took the ferry across the river to explore the breweries in Williamsburg, which was such a fun adventure. This was truly the perfect couples’ retreat, and I can’t wait to come back!

ESVA Silver Beach Getaway - Book Summer 2025 now!
Such a cute, well stocked and clean cottage. Extremely quiet neighborhood. Sunsets over the bay were stunning. Jennifer was easy to teach and communicate with.

Sunset Haven
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!

The Beach Nest. Walk to oceanfront.
How lucky my wife and I were to find the Beach Nest in Virginia Beach. The location is beautifully appointed and perfect for a couple looking to be near the beach, restaurants and all that the strip has to offer. The attention to detail with the accommodations was second to none. A 5 star experience. Ted and Lori were such a nice couple and provided us ample information for entertainment and dining in the area. Highly recommended.

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....
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- Busch Gardens Williamsburg
- Carytown
- Bethel Beach
- Buckroe Beach
- Kingsmill Resort
- Brown's Island
- Virginia Beach National Golf Club
- First Landing State Park
- Pocahontas State Park
- Buckroe Beach and Park
- Golden Horseshoe Golf Club
- Grove Beach
- Sarah Constant Beach Park
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- Haven Beach
- Jamestown Settlement
- Royal New Kent Golf Club
- Norfolk Botanical Garden
- Hollywood Cemetery
- Science Museum of Virginia
- Jungle Golf
- Chrysler Museum of Art