Holiday Rentals in Gloucester

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Holiday Rentals in Gloucester

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (89)
"We loved our stay. We were looking for somewhere away from the chaos of holiday in Williamsburg but accessible. It fit perfectly. House was quiet, clean and comfortable. Made for a wonderful weekend. "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Welcome to this Waterfront Home with Amazing Views

10.0 out of 10, Exceptional, (19)
"Cozy!Clean!Great outdoor!"
The price is €373
includes taxes & fees
10 Jan - 11 Jan
Welcome to this Waterfront Home with Amazing Views

Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock

10.0 out of 10, Exceptional, (24)
"Great property. Wonderful views. Quiet and peaceful. Hosts were tremendous with their instructions and details regarding our stay."
Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock

Historic Cottage on Ware River Estate

10.0 out of 10, Exceptional, (257)
"The cottage was a wonderful place to get away and decompress. We loved the peaceful location and side trips to Williamsburg and Gloucester. Would love to return. "
Historic Cottage on Ware River Estate

Radiant Gloucester House w/ Private Porch!

9.4 out of 10, Exceptional, (20)
"What a wonderful place to stay! The home is incredible, with an amazing sunroom and excellent kitchen! Wish we could transport the entire place into our actual apartment — very lovely, and such a nice treat to experience the town of Gloucester. Hope to stay here again!"
Radiant Gloucester House w/ Private Porch!

Relaxing Riverfront Cottage w/ Boat Dock!

9.8 out of 10, Exceptional, (29)
"We came for the Urbanna oyster festival and found the cottage to be a perfect landing spot for us. Charming, clean, beautiful view, and well stocked! "
Relaxing Riverfront Cottage w/ Boat Dock!

Private 5-acre Waterfront Peninsula with Beach

9.2 out of 10, Wonderful, (35)
"We had such a wonderful time! The location was absolutely beautiful and so peaceful. The house was very comfortable and clean making it easy to just relax. Note to future renters - the property and it's amenities have been greatly loved. The peddle boat rudder wasn't working, one of the kayaks was cracked and leaking, hot tub never got up to temperature, several nails were popping up out of the deck which had several loose boards and splinters, and the kitchen needed some work as the knobs were...
The price is €739
includes taxes & fees
9 Jan - 10 Jan
Private 5-acre Waterfront Peninsula with Beach

Cottage on a Private Island in the York River

10.0 out of 10, Exceptional, (323)
"The cottage on the river is serene. The property is furnished to take advantage of the outdoors."
Cottage on a Private Island in the York River

Relaxing 1 bedroom 2019 Camper beside the Seven River

9.4 out of 10, Exceptional, (18)
" The location was great if you want a quiet place and close to the river. We enjoyed walking down to edge and watching the water. We also enjoyed walking around the neighborhood. The camper was very clean. Kimberly and her husband were very nice and helped with the few little problems that we had. We really enjoyed our stay there."
The price is €155
includes taxes & fees
7 Jan - 8 Jan
Relaxing 1 bedroom 2019 Camper beside the Seven River

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (40)
"We have stayed at Glenda’s place multiple times and love it every time. It’s the perfect place to reconnect with my family and enjoy the peace of the Rivah. Everything is clean and comfortable and well stocked. Thank you Glenda!"
Cozy cottage on the Chesapeake Bay

Uncle Bill's Lodge & Soccer Pool Showdown

8.4 out of 10, Very good, (7)
"Perfectly clean and comfortable but no privacy. Pet friendly but neighbor allowed their dog to come to fenced yard at all hours which made my 1 dog bark. Not sure if neighbor was owner. Great fenced yard but as I stated, no privacy. Homes close by even in backyard. Fine for families who want to visit from out of town visiting Busch Gardens/Water Country and CW as backyard is entertaining and home is affordable. Just not what we were looking for. Photos and description made us feel it would be...
Uncle Bill's Lodge & Soccer Pool Showdown

Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

10.0 out of 10, Exceptional, (130)
"Kingsmill is a lovely property, very convenient to local attractions. The condo was clean and well furnished. "
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

9.8 out of 10, Exceptional, (123)
"Like a hotel room without amenities such as ice, extra toilet paper."
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Super close to beaches, the historic triangle, and bush gardens!

8.2 out of 10, Very good, (24)
"Never saw any roaches like some reviews stated "
Super close to beaches, the historic triangle, and bush gardens!

Chickahominy Riverside Guest Home 30 Minutes to Williamsburg!

9.4 out of 10, Exceptional, (21)
"My family gathered at this property to celebrate the birthdays of our 2 kids. 3 of us stayed on property and others traveled to join us for the day. Beautiful property! It is clean and well kept. Our labrador retreiver particularly loved the access to water at the next door boat launch. The downstairs apartment has a GREAT game room. We enjoyed playing air hockey, pool, video games, and watching sports on the enormous TV. We also enjoyed the fire pit one of the nights we were there. So...
Chickahominy Riverside Guest Home 30 Minutes to Williamsburg!

The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!

9.6 out of 10, Exceptional, (19)
"The property is very secluded, You feel like the world is behind you. It is peaceful and quiet, The sound of nature will be the only symphony you’ll hear. I love the private beach area. We fished and caught some crab on the boat deck. The house is a bit old but that is where the charm is. There was some bug in the house but that was expected. Overall we had great time. "
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!

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

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

Charming Boutique Hotel close to Williams and Mary College

2.0 out of 10, (4)
"Very dirty, killing bugs every day "
Charming Boutique Hotel close to Williams and Mary College

The Crab Shack on Carter's Creek

10.0 out of 10, Exceptional, (72)
"The place was sparkling clean, the host was really gracious and helpful. The pullout couch is a really high quality brand feels like a true bed. Thank you for a great stay!"
The Crab Shack on Carter's Creek
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 types of properties in Gloucester you may be interested in

Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock

10.0 out of 10, Exceptional, (24)
"Great property. Wonderful views. Quiet and peaceful. Hosts were tremendous with their instructions and details regarding our stay."
Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 star property
9.0 out of 10, Wonderful, (2597)
"We stayed the Hilton Historic Powhatan for a five day family vacation. The property was easy to find and check in went smoothly. Our room was upgraded. The property is huge with multiple water features, walking/running paths, playground, mini golf, and other outdoor activities. Our unit was a second floor two bedroom with full kitchen and washer/dryer. The bedrooms and bathrooms were very spacious and clean. The kitchen was clean and functional and had all the essential cooking items you would...
The price is €94
includes taxes & fees
2 Feb - 3 Feb
Hilton Vacation Club The Historic Powhatan Williamsburg

Vacation Village At Williamsburg

3.0 star property
8.8 out of 10, Excellent, (1096)
"My family and I always stay here and enjoy it every time."
The price is €215
includes taxes & fees
8 Jan - 9 Jan
Vacation Village At Williamsburg
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.

Frequently asked questions

Can I find a holiday rental in Gloucester?

Yes, we offer holiday rentals where you'll be only 13.8 mi (22.2 km) from Busch Gardens Williamsburg, offering you a more remote option if you want a quiet place to stay. Gloucester is known for its festivals and art.

What are some of the best holiday rentals that Gloucester has to offer?

"Bee Haven" Cottage Retreat Near Colonial Williamsburg: This highly rated holiday home rental in Gloucester is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Gloucester are Welcome to this Waterfront Home with Amazing Views and Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock.

How many holiday rentals are there in Gloucester?

Expedia has 20 holiday rentals for your stay in Gloucester.

What’s there to see and do in Gloucester?

Middle Peninsula State Park and Captain John Smith National Historic Trail are a couple of scenic spots to enjoy the outdoors, whereas Gloucester Museum of History is one of the cultural attractions. Other places in town to visit include Main Street Center and Gloucester Public Library.

What’s a holiday rental in Gloucester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gloucester. Holiday rentals feature amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for small groups.