Holiday Rentals in Gloucester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Gloucester

Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock
10.0 out of 10, Exceptional, (22)
"We enjoyed our stay. The location was peaceful and relaxing and the sunsets were incredible. "
Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (81)
"This adorably decorated home is situated in a quiet, tree-dense neighborhood with easy access to the highway if you’re spending the day outside of town. The town of Gloucester is quaint, filled with friendly people, and many dining options. The host made the stay easy, welcoming, and lovely. The home is absolutely sweet. Comfy decor, very clean, great kitchen, and comfy beds. Parking is ample and the views from every window are picturesque. The only “word of caution” is that the water does have...
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, (17)
"Very nice home. Beautiful dock. Great location. Very clean."
The price is €396
includes taxes & fees
11 Nov - 12 Nov
Welcome to this Waterfront Home with Amazing Views
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (255)
"My wife and I enjoyed our stay here very much. The property was beautiful, and the dock fishing area was really cool. The town was cute and the restaurants we went to were delicious. We recommend staying here."
Historic Cottage on Ware River Estate
Radiant Gloucester House w/ Private Porch!
9.6 out of 10, Exceptional, (16)
"Wonderful "
Radiant Gloucester House w/ Private Porch!
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (32)
"There were so many things to do at this beautiful location! We enjoyed boating, swimming, crabbing, disc golf, bonfires, games, and more! The house comfortably sleeps 21 people! It’s a lovely house that has an incredible view and it’s so quiet and relaxing. "
The price is €737
includes taxes & fees
2 Dec - 3 Dec
Private 5-acre Waterfront Peninsula with Beach
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (317)
"This is our 3rd trip to this quiet little island. It is a great place to relax, and there is plenty to do in Williamsburg & Yorktown. We will be back!"
Cottage on a Private Island in the York River
Cozy cottage on the Chesapeake Bay
10.0 out of 10, Exceptional, (34)
"Beautiful views, plenty of room, and an amazing dock. We went crabbing and caught lots of blue crab right off the dock. I absolutely loved our time here and would definitely come back again. Thank You!"
Cozy cottage on the Chesapeake Bay
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.8 out of 10, Exceptional, (119)
"Quick weekend stay for a baby shower. The condo was clean and well stocked, host was very responsive. We enjoyed our stay."
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Relaxing 1 bedroom 2019 Camper beside the Seven River
9.2 out of 10, Wonderful, (16)
"Camper was clean and cozy. A little hard to find and water on the road a little alarming. Property was not as clean as pictures presented. It was quite."
The price is €142
includes taxes & fees
4 Dec - 5 Dec
Relaxing 1 bedroom 2019 Camper beside the Seven River
Enjoy family fun and Sunsets at Piankatank Point.
9.8 out of 10, Exceptional, (45)
"This house was perfect for a weekend getaway. Enjoyed the dock, kayaks, and pool table!"
Enjoy family fun and Sunsets at Piankatank Point.
Restored 1920's Cottage on 1 Acre w/ Fire Pit
9.4 out of 10, Exceptional, (52)
"The property is very beautiful. I would not say it has a river view, but it is very shaded and pretty. The house serves basic needs. Clean and comfortable beds. Clean, functioning bathroom. We used this as home-base while visiting son, DIL and grandson for his 1st birthday. "
Restored 1920's Cottage on 1 Acre w/ Fire Pit
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (68)
"Eclectic cottage the way they where originally done. Perfect location for never ending views. The full moon casting its glow over the water was perfect."
Oceanfront White Stone Cottage w/ Private Beach!
Sojourn Aviators Dream on Back River
9.6 out of 10, Exceptional, (14)
"We picked this location given friends live nearby, but it exceeded expectations. Beautiful view, incredible sunrise, and the kids loved the fireplace. Hadn't realized the kids bunk room doesn't have a door to close, but luckily noise wasn't a problem. "
The price is €346
includes taxes & fees
6 Nov - 7 Nov
Sojourn Aviators Dream on Back River
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground
9.8 out of 10, Exceptional, (10)
"The house was beautiful! So spacious and clean we Love Love Loved It‼️‼️"
The price is €576
includes taxes & fees
17 Nov - 18 Nov
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (122)
"Family and dog had a wonderful time at this off-the-beaten path waterfront gem. Great water access and beautiful views from the screened porch. Enjoyed crabbing, beach walks at nearby preserve, sunrises, quaint town w cute shops."
Private, 7-acre waterfront retreat on Winter Harbor Haven
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
Super close to beaches, the historic triangle, and bush gardens!
8.2 out of 10, Very good, (23)
"We had a great time staying in Hampton, at this location. And the hot tub was great. "
Super close to beaches, the historic triangle, and bush gardens!
Riverfront Cottage: Fire Pit & Kayaks
9.8 out of 10, Exceptional, (31)
"It was very small. Bathroom shower was slippery and unsafe. Property was very neat, clean, well-stocked, and check-n was easy. HVAC system was wonderful. We could not walk down to the dock due to having knee replacement surgery and no handrails. Very little to no shade from the sun even on the back porch."
Riverfront Cottage: Fire Pit & Kayaks
Anvil Campground
2.5 star property
8.4 out of 10, Very good, (34)
"Nothing to do and over priced. Train went by cabin 3 all night long. Everything closed at 8 and even the game room. Very small cabins with no bathroom. Will never stay again "
The price is €84
includes taxes & fees
14 Nov - 15 Nov
Anvil Campground
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.
Don't see what you're looking for?
See all available properties in Gloucester
Save an average of 15% on thousands of hotels when you're signed in

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, (22)
"We enjoyed our stay. The location was peaceful and relaxing and the sunsets were incredible. "
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, (2570)
"The suites on the ground floor are Fabulous!"
The price is €101
includes taxes & fees
24 Nov - 25 Nov
Hilton Vacation Club The Historic Powhatan Williamsburg
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
3.0 star property
8.8 out of 10, Excellent, (1074)
"Check-in was great, the staff was super friendly! They were very informative of the property and layout. Our room is nice and clean. The one negative so far for our room is the mini refrigerator doesn’t work and we had hoped to chill some beverages. The ice maker near our room doesn’t work. Neither does the one on the first floor. We had to go halfway around the building to find ice. We do like that the property is close to Colonial Williamsburg. There are shuttles and also a nice walking path...
The price is €125
includes taxes & fees
1 Dec - 2 Dec
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
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 Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock and Welcome to this Waterfront Home with Amazing Views .

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 Brown Park 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.