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Compare 111 Cottages in Gloucester with updated reviews, rates, and availability.

Cottage on a Private Island in the York River

10.0 out of 10, Exceptional, (327)
"Our Stay was wonderful, restful, just what we needed..Hosts were terrific & responsive....We hope to come back"
Cottage on a Private Island in the York River

Private 2,000 Sq Ft Cottage in Historic Yorktown- w/ trolley access

10.0 out of 10, Exceptional, (197)
"Lovely cottage, close to downtown Yorktown. Very comfortable stay."
Private 2,000 Sq Ft Cottage in Historic Yorktown- w/ trolley access

Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

10.0 out of 10, Exceptional, (115)
"Thank you so much for a wonderful stay! We really enjoyed our time at your beautiful house. Everything was well kept, very clean, very organized. You can tell Armando really keeps up with the house and makes sure it is welcoming to guests. Very close to Williamsburg, Jamestown, etc. "
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

Private 1300 sq ft Cottage in Historic Yorktown-w/ trolley access

10.0 out of 10, Exceptional, (137)
"This cottage is beautifully decorated, clean and in a quiet neighborhood within convenient walking distance from the historic district and the York River. "
Private 1300 sq ft Cottage in Historic Yorktown-w/ trolley access

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

10.0 out of 10, Exceptional, (147)
"Beautiful property. Well maintained. Location is quiet, peaceful and secluded. Lovely views. A completely relaxing vacation in a beautiful location. Perfect place to unwind. "
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

St. Paddy’s Day is almost here. Come celebrate the Green in Irvington!

10.0 out of 10, Exceptional, (287)
"We had a very pleasant stay at the Key Cottage. Everything we could have wanted was available, the house was immaculate, and the location and neighborhood were perfect. Communication was excellent with the host and we are truly looking forward to a return visit."
St. Paddy’s Day is almost here. Come celebrate the Green in Irvington!

Waterfront Cottage with Private Beach, Sunsets over Water

10.0 out of 10, Exceptional, (198)
"This was just what we needed for our holiday trip. The water views were great, saw various water birds including geese and a heron that posed for us out back. The place was clean and had all of the amenities of home. We are considering making this a holiday tradition!"
Waterfront Cottage with Private Beach, Sunsets over Water

Bubba Butler's Cottage

9.8 out of 10, Exceptional, (7)
"We found this property to fit our needs perfectly. Close proximity to Urbana, Irvington and Kilmarnock. The older home, on the Rappahannock River had been refurbished for today’s needs but retained some fun, and not so fun quirks! Nothing too serious… the water stream in the shower returned after the system built pressure back up.. Would return."
Bubba Butler's Cottage

Bee Humble Cottage w/in 20mins to Public Beaches

9.8 out of 10, Exceptional, (23)
"I cannot say enough good things about our stay at the be humble cottage. I don't think pictures can even do this property or neighborhood justice. We were so excited to walk inside and see a beautifully decorated cottage. Our hosts were so diligent in making sure to have an entire binder full of things to do and recommendations all around town. I wish our stay was longer but we are now customers for life for the Bee Humble cottage and community. "
Bee Humble Cottage w/in 20mins to Public Beaches

Relaxing Riverfront Cottage w/ Boat Dock!

3.0 star property
10.0 out of 10, Exceptional, (1)
Relaxing Riverfront Cottage w/ Boat Dock!

ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest

9.8 out of 10, Exceptional, (238)
"We were at "Analog" for the long Thanksgiving weekend. The fall leaves and river view were stunning. House stayed warm and cozy, and we fixed a complete Thanksgiving meal in the very well appointed kitchen, including pie pans and platters and attractive dinnerware. Not too hard to take the 24-hr/7 day free ferry that runs every 20 minutes over to see sights in the historic triangle. We were very happy we chose this remote-feeling scenic location vs. the rather Disney-ish condos closer to...
ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest

3 BR Bay Home w Private Dock & all the Amenities

10.0 out of 10, Exceptional, (10)
"My family and I have stayed at countless properties over the years through VRBO. As a family of five (5), including two teens, and an 8-year-old, one can imagine the difficulties associated with finding a vacation rental that had something that tickled the fancy of each. We’ve been very happy with the properties and the accuracy of the listings. There has never been an occasion where any of us felt deceived or that the property failed to meet expectations. With that said, our recent stay at this...
The price is SAR 1,219
SAR 2,784 total
includes taxes & fees
16 Mar - 17 Mar
3 BR Bay Home w Private Dock & all the Amenities

Modern Beachfront Cottage with Endless Bay Views

9.8 out of 10, Exceptional, (66)
"Stayed for 3 days- the views were absolutely amazing (sunrise and sunset). All the neighbors we very friendly. Town was a short drive away with some great food. Will absolutely be returning."
Modern Beachfront Cottage with Endless Bay Views

Romantic Waterfront Abode with Patio & Dock!

9.8 out of 10, Exceptional, (49)
"Cozy and comfortable, very relaxing and quiet."
Romantic Waterfront Abode with Patio & Dock!

Waterfront Gloucester Cottage w/ Private Boat Dock

9.4 out of 10, Exceptional, (6)
"Quick trip to VA for dad to visit with family and friends. House was clean, updated, well furnished, and sized right for the trip. Cool weather prevented our use of all outside amenities. Showers/bathrooms were small. Televisions took awhile before channels loaded for viewing. Price seemed very reasonable until they added all of the fees and taxes that almost doubled the cost. Would still use again if travel to Gloucester in future...especially if price was better. "
Waterfront Gloucester Cottage w/ Private Boat Dock

Riverfront Cottage w/ Private Beach Near Wmsburg

10.0 out of 10, Exceptional, (17)
"It was such an amazing quiet little house, we unfortunately had to leave early due to bad weather at our house but we plan on coming back in the summer!"
Riverfront Cottage w/ Private Beach Near Wmsburg

Waterfront Deltaville Cottage w/ Fire Pit!

9.2 out of 10, Wonderful, (5)
"The home and location are very nice and as described. The reason I am ranking only 3-stars is because the house was very hot when we arrived. We turned the AC to 71 degrees, yet the WYZE thermostat kept remotely changing to 79 degrees. It was about 95 degrees outside, so we couldn’t find any relief from the heat. I contacted the owner a couple of times about the temp changing and was told “Sorry! We’re out of town”. Ultimately, the thermostat shut off completely. We tried to turn it back on with...
Waterfront Deltaville Cottage w/ Fire Pit!

Private Country Retreat with Swimming Pool

10.0 out of 10, Exceptional, (130)
"Perfect place for our small family and dogs - clean, comfortable, quiet, well-appointed place with everything we needed for a few days. Lovely touches in and outdoors. Communication with the owner was great. Highly recommend if you want to get away from the world for a few days!"
The price is SAR 1,095
SAR 2,159 total
includes taxes & fees
16 Mar - 17 Mar
Private Country Retreat with Swimming Pool

Restored 1920's Cottage on 1 Acre w/ Fire Pit

9.4 out of 10, Exceptional, (62)
"Fantastic! great location, fully equipped and appropriate for our life stylel"
Restored 1920's Cottage on 1 Acre w/ Fire Pit

Oceanfront White Stone Cottage w/ Private Beach!

7.4 out of 10, Good, (70)
"Just what we were looking for,great bay view ,off the beaten path"
Oceanfront White Stone Cottage w/ Private Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Gloucester

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (93)
"Great place for families with pets and/or small kids! So nice that the host provides toys and dog treats. My family had a great stay here."
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

9.8 out of 10, Exceptional, (148)
"Very clean and nicely decorated. Awesome back porch with beautiful views."
A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

Welcome to this Waterfront Home with Amazing Views

10.0 out of 10, Exceptional, (21)
"Lovely stop over on our way to family. Beautiful home decorated for the holidays and had all the amenities we needed plus little snacks! We got to the a beautiful sunset off the dock and our twins got their own rooms and bathroom. It would’ve cost more to get two rooms at Williamsburg hotel. So happy we got to stay here! Would love to stay the week during summertime! Beautiful home and location! "
Welcome to this Waterfront Home with Amazing Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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