Gloucester Vacation Rentals

Vacation Rentals in Gloucester

Property grounds
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (241)
"Excellent base for exploring Williamsburg, Yorktown and Jamestown. Beautiful historic cottage on expansive grounds. Dead quiet."
Historic Cottage on Ware River Estate
Fridge, microwave, oven, stovetop
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (62)
"Seriously, don't think twice about booking this property! It's in a beautiful, quiet setting and about an hour drive from countless attractions. We went to Williamsburg, short 45 minute drive through beautiful country. The property is exceptional! The host has thought of literally everything and well appointed. Looking forward to returning soon!"
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Fridge, microwave, oven, stovetop
Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, (11)
"Thank you so much for sharing this rental. My family loved being on the water and all were just overwhelmed by the rental. All have rented VRBOs before and all remarked how clean. Also appreciated the good basket, area information and check-out list. As the relative who rented the property, the owners were very responsive to my questions. I'll rent again for family."
The price is $150
$318 total
includes taxes & fees
May 20 - May 21
Welcome to this Waterfront Home with Amazing Views
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View from property
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed the views and experience of Chesapeake Bay as a family. The natural surroundings of the bay spoke to my need to connect with nature, US history, my family, and my partner. The house was accommodating and well kept which was much appreciated for a family such as ours that is extended, loves to spend time, and cook together. We had all of the luxuries of feeling at home but being away all the same, with the space we all needed for comfort. I would recommend this house for the...
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
Fridge, microwave, stovetop, coffee/tea maker
NO CHILDREN UNDER 5.. Smoking outside with doors and windows closed. No animals.
10.0 out of 10, Exceptional, (122)
"Yeah... relaxing"
The price is $175
$212 total
includes taxes & fees
May 19 - May 20
NO CHILDREN UNDER 5.. Smoking outside with doors and windows closed. No animals.
Exterior
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (302)
"We had a very enjoyable stay. Peaceful, quiet, tranquil. Thoroughly enjoyed it. Met with longtime friends for a getaway. The place isn't fancy, but we weren't looking for fancy, just a quiet hideout. Would stay again."
Cottage on a Private Island in the York River
Fridge, microwave, oven, stovetop
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, (3)
"Extras were a delightful touch, didn't need anything during our stay. Host was quick to respond, location was close to stores and everything we needed."
The price is $114
$217 total
includes taxes & fees
May 15 - May 16
Hampton Centrally Located Oasis
Fridge, microwave, oven, stovetop
Luxurious 3 Bedroom Condo Sleeps 8!
10.0 out of 10, Exceptional, (76)
"Kingsmill Resort was a beautiful setting. The location was great - very close to major attractions. The condo was very clean with comfortable, lovely furnishings. The en suite bedrooms and common area were a perfect fit for our 3 adult couples. The kitchen was well stocked and we appreciated the complimentary coffee. The host was responsive and friendly. I highly recommend this unit for a very pleasant stay."
Luxurious 3 Bedroom Condo Sleeps 8!
Beach nearby, beach towels
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
10.0 out of 10, Exceptional, (119)
"Comfortable, clean and the location was great."
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (111)
"Beautiful home. Very well equipped."
Private, 7-acre waterfront retreat on Winter Harbor Haven
Property grounds
Sojourn Aviators Dream on Back River
10.0 out of 10, Exceptional, (7)
"4 sisters getting together to laugh and reminisce. We had a blast. The house was great and met our every need."
The price is $185
$462 total
includes taxes & fees
May 15 - May 16
Sojourn Aviators Dream on Back River
Property grounds
Peaceful Waterfront Cottage on VA’s Northern Neck
10.0 out of 10, Exceptional, (87)
"We loved our stay at Fred’s property. Unfortunately the weather didn’t cooperate enough for us to enjoy the water, but the views and cozy cottage provided a relaxing time away nonetheless. Location was great — off the beaten path but still a quick drive to town."
Peaceful Waterfront Cottage on VA’s Northern Neck
Property grounds
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
10.0 out of 10, Exceptional, (177)
"Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back."
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
Interior
Amazing views of the Chesapeake Bay.
10.0 out of 10, Exceptional, (10)
"We were in town for a reunion with good friends and former neighbors. This cottage was perfect for our needs! Spacious and comfortable. Kitchen stocked with everything you might need. Great view of the river and a covered front porch to sit and enjoy it! Lovely area to walk around as well. Host very responsive! I would definitely stay here again. Highly recommend!"
Amazing views of the Chesapeake Bay.
Interior
Radiant Gloucester House w/ Private Porch!
9.8 out of 10, Exceptional, (11)
"The house was very comfortable and clean with everything provided for the stay. The location is on a quiet street yet only a short walk to an incredible sweet shop and great restaurant. It was awesome to sit on the sun porch and listen to the birds chirping. We loved it."
Radiant Gloucester House w/ Private Porch!
Property grounds
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.8 out of 10, Exceptional, (102)
"The unit was very nice and perfect for what we needed. Cute community with scenic grounds and plenty of food options nearby. Check in was easy and check out time was generous. It was a perfect centrally located spot for us to do some regional college visits! Would definitely stay here again when we come back for Busch Gardens."
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Outdoor spa tub
Enjoy family fun and Sunsets at Piankatank Point.
9.8 out of 10, Exceptional, (38)
"Everything you want to do is right there at the house..Fishing, crabbing. Canoeing, kayaking and so much more. Already planning a trip back this summer."
Enjoy family fun and Sunsets at Piankatank Point.
On the beach, beach towels
ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest
9.8 out of 10, Exceptional, (232)
"Words cannot describe the absolute serenity that this property offers. Jeff was amazing in all aspects of the communication and check in. The house was perfect and far exceeded expectations, and the property checked every box. The owners pride and attention to detail is unparalleled and show is all aspects of the property. We have traveled to many places and this is by far the absolute best. There is nothing that we wanted or needed while there and loved the solitude. We can’t wait to return...
ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest
Property grounds
The Little Blue Cottage - Topping : Waterfront!
9.8 out of 10, Exceptional, (28)
"Inside decor was spot on. Kitchen was well-stocked, and we enjoyed the dock and fishing. Host was a great communicator."
The Little Blue Cottage - Topping : Waterfront!
TV, fireplace, DVD player, books
Riverfront Cottage: Fire Pit & Kayaks
9.8 out of 10, Exceptional, (25)
"It was beautiful. We loved wake up to the beautiful water everyday."
Riverfront Cottage: Fire Pit & Kayaks
Don't see what you're looking for?
See all available properties in Gloucester
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.

Other types of properties in Gloucester you may be interested in

View from property
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed the views and experience of Chesapeake Bay as a family. The natural surroundings of the bay spoke to my need to connect with nature, US history, my family, and my partner. The house was accommodating and well kept which was much appreciated for a family such as ours that is extended, loves to spend time, and cook together. We had all of the luxuries of feeling at home but being away all the same, with the space we all needed for comfort. I would recommend this house for the...
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
Garden
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
3.0 star property
8.8 out of 10, Excellent, (1001)
"Check-in was great. She was detailed and friendly and told us about the property. Beds were a bit firm and I could feel one of the bed coils but not enough to bother me. Their pillows were overly filled and uncomfortable. Bathroom ok, yes outdated but it serves the purpose. Room was big and spacious. Free breakfast included but we did not get to check it out because our room was so far from the breakfast area and wanted to sleep in more. Reading previous reviews about breakfast didn't feel...
The price is $117
$150 total
includes taxes & fees
May 15 - May 16
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Vacation Village At Williamsburg
3.0 star property
8.6 out of 10, Excellent, (1001)
"This was a last minute trip with my family on Mother's Day weekend! The property was wonderful. The room was amazing for the cost. Spacious. The staff was friendly. The room and grounds had everything we needed. Only thing is that it's a little farther Way from Busch Gardens than we thought, but that has nothing to do with the grounds. We will stay longer next.time "
The price is $217
$255 total
includes taxes & fees
May 16 - May 17
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 vacation rental in Gloucester?

Yes, we give you a choice of vacation 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 quieter place to stay. Gloucester is known for its festivals and art.

What are some of the best vacation rentals in Gloucester?

"Bee Haven" Cottage Retreat Near Colonial Williamsburg: Visitors like this Gloucester vacation home rental. It is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Gloucester?

Expedia has 21 vacation rentals for your stay in Gloucester.

What’s there to see and do in Gloucester?

Cultural attractions include Gloucester Museum of History, whereas Middle Peninsula State Park is a spot to enjoy nature. In the larger area, you’ll find Rosewell Ruins and Busch Gardens Williamsburg.

What’s a vacation rental in Gloucester like?

Vacation rentals are privately owned properties where you can stay for a couple of days or more in Gloucester. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.