Gloucester Holiday Rentals

  • 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

Radiant Gloucester House w/ Private Porch!

9.6 out of 10, Exceptional, (16)
"Wonderful "
Radiant Gloucester House w/ Private Porch!

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (85)
"Great location to see the birth of our nation. House very clean and very quiet neighborhood. Appliances clean and work well stocked kitchen rules were few and simple if I had to say anything bad it would have to be the water I would bring in my drinking water "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Welcome to this Waterfront Home with Amazing Views

10.0 out of 10, Exceptional, (18)
"Gorgeous quiet property, clean and well appointed with additional small touches to make for a lovely welcome and stay (eg coffee to get started, shower gel/soap, clocks in bedrooms, nightlights, railings for stairs into property which was really helpful having my 87yr mother with me who has some mobility challenges). Wonderful (lit) dock to enjoy, watching the world (and egrets!) go by. Fabulous local country store nearby and a great central location for exploring the area. Very responsive host....
The price is AU$594
includes taxes & fees
9 Dec - 10 Dec
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

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!

Cottage on a Private Island in the York River

10.0 out of 10, Exceptional, (319)
"Give yourself 24 hours to settle in. We arrived in perfect weather for a 4 day respite and only for one day, with land breezes, did we experience some pesky flies. The fresh salt air, wide star-lit skies, 24/7 quiet and mesmerizing moon-glow off the waters, 360 degrees worth, more than make up for any such small annoyance. There is some history to appreciate about the island and the cottage. When you find yourself first thing in the morning checking the tide schedules, you will then realize...
Cottage on a Private Island in the York River

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!

Waterfront Cottage with Private Beach, Sunsets over Water

10.0 out of 10, Exceptional, (194)
"The house was very clean upon entering and the view was beautiful. It was conveniently located to shops and restaurants. We enjoyed visiting the nearby Hatchery while there. "
Waterfront Cottage with Private Beach, Sunsets over Water

Anvil Campground

2.5 star property
8.2 out of 10, Very good, (35)
"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 AU$141
includes taxes & fees
25 Nov - 26 Nov
Anvil Campground

Oceanfront White Stone Cottage w/ Private Beach!

7.4 out of 10, Good, (69)
"Just what we were looking for,great bay view ,off the beaten path"
Oceanfront White Stone Cottage w/ Private Beach!

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

Relaxing 1 bedroom 2019 Camper beside the Seven River

9.2 out of 10, Wonderful, (17)
" 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 AU$234
includes taxes & fees
2 Dec - 3 Dec
Relaxing 1 bedroom 2019 Camper beside the Seven River

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!

Enjoy family fun and Sunsets at Piankatank Point.

9.8 out of 10, Exceptional, (47)
"Quiet place, loved the water view"
Enjoy family fun and Sunsets at Piankatank Point.

Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

9.4 out of 10, Exceptional, (114)
"Excellent place to enjoy 4 generations of my family. Plenty of space to play with my grandkids outside and games to enjoy on the inside. Very quiet neighborhood and plenty of privacy."
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

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 AU$635
includes taxes & fees
15 Dec - 16 Dec
Sojourn Aviators Dream on Back River

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (37)
"The house was perfect for our weekend. Great views! The house had everything we needed. Appreciated all the extras like toilet paper, paper towels, condiments, coffee, and more. Super easy to check out. Sidenote, the only TV is in the master bedroom. Would probably be useful if the TV stand had wheels so it could be pulled into the living room for everybody to watch a movie. The house is 15 minutes away from a small winery, with tons of wine and food options and the town of Matthews, with a...
Cozy cottage on the Chesapeake Bay

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

10.0 out of 10, Exceptional, (128)
"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!

Uncle Bill's Lodge & Soccer Pool Showdown

9.4 out of 10, Exceptional, (6)
"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
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

Vacation Village At Williamsburg

3.0 star property
8.8 out of 10, Excellent, (1011)
"Nice room for a family. Good selection of recreational activities on the property. "
The price is AU$317
includes taxes & fees
26 Nov - 27 Nov
Vacation Village At Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 star property
9.0 out of 10, Wonderful, (2566)
"Luxurious condo. Very comfortable. "
The price is AU$144
includes taxes & fees
1 Dec - 2 Dec
Hilton Vacation Club The Historic Powhatan 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 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 Fairfield Foundation and Main Street Center.

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.