Gloucester Holiday Rentals

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Holiday Rentals in Gloucester

Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (242)
"Cute cabin. Porch was perfect in the morning. Listening to the birds while drinking coffee was relaxing. Location was perfect as we have family in Onemo. It was a relaxing & perfect."
Historic Cottage on Ware River Estate
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
10.0 out of 10, Exceptional, (14)
"We stayed here during a visit to the historic triangle, Williamsburg, Yorktown and Jamestown with our two daughters and two dogs. Maybe we didn't read it right, but we unexpectedly. We're thrilled to find a fence in yard. The dock was nice for fishing and while we didn't use the boats, it's nice that they were there as well. The house was clean and plenty big for all of us. It's about 40 minutes to Williamsburg and a little further to Busch gardens but we were able to have all the amenities...
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (67)
"Three ladies and one nice dog for three nights in a sweet and cozy cottage? Yes, please! Bee Haven was spotless and charming. I would definitely book again if I ever find myself in this area. Thank you!"
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
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Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, (14)
"The description of the property does no justice once you arrive. It’s very quiet, as clean as can be, and everything that is listed is correct. There is now a beautiful new pier in the back yard for easy launching of the kayaks, which the kids enjoyed every afternoon. The owners were very easy to communicate with during our stay and were very accommodating. Would definitely recommend!"
The price is AU$636
includes taxes & fees
16 July - 17 July
Welcome to this Waterfront Home with Amazing Views
Radiant Gloucester House w/ Private Porch!
9.8 out of 10, Exceptional, (12)
"Beautifully restored interior. Air conditioning worked great. Quiet street but only steps to Main Street. Especially good for visiting residents at Riverside Sanders which is just a block away."
Radiant Gloucester House w/ Private Porch!
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (28)
"I held my daughters 18th birthday party here, and it was incredible! Plenty of room for hanging out and great for overnight guests (lots of rooms and places to sleep). Beautiful house, inside and out! Lots of things to keep people busy and entertained, but just as many for relaxing. Fantastic stay overall with a wonderful host!!! Would absolutely recommend."
The price is AU$1,959
includes taxes & fees
11 July - 12 July
Private 5-acre Waterfront Peninsula with Beach
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
9.4 out of 10, Exceptional, (108)
"Truly amazing stay! The house is terrific and a great place to be out of the way of the bustle, while still remaining close enough to nearby activities. Like i said, we were blown away by how much better the property is than the listing gives it justice! It was a bit confusing to find the first time, as the number isnt displayed on the road. But if you have sharp eyes, you'll find it. If you want to swim, pay attention to what the tides are doing. But the water was amazing. Only true complaint:...
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
10.0 out of 10, Exceptional, (121)
"Great condo in a great location. Couple minute drive to Busch gardens or colonial Williamsburg without feeling like you’re in a tourist spot. Groups were beautiful and it’s a gated community."
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, (106)
"Was able to use the amenities on the resort, as all the workers were so nice. Room was very nice but the overhead shower didn’t work. Luckily had an extra shower head we could use. My best friend and I decided to make this a yearly trip the first week of June so be ready for next summer!"
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Restored 1920's Cottage on 1 Acre w/ Fire Pit
9.4 out of 10, Exceptional, (45)
"My daughter, granddaughter and I stayed for 3 nights. It was wonderful. I wish we could have stayed longer."
Restored 1920's Cottage on 1 Acre w/ Fire Pit
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, (5)
"Our stay was awesome! This cute little place was perfect for me and my friend. It was cozy and just made the trip that much better! Owner is super nice and was easy to get ahold of. I would recommend this place to anyone, and I wil definitely be booking again in the future!"
The price is AU$323
includes taxes & fees
30 June - 1 July
Hampton Centrally Located Oasis
Relaxing 1 bedroom 2019 Camper beside the Seven River
9.8 out of 10, Exceptional, (10)
"Although the actual camper was not the one advertised, our stay was filled with all the expected amenities Kimberly described. In a previous review someone mentions the rooster, he was quite pleasant, not at all like described in their review. The camper behind ours was closer than I would expect and not in the description, but it was not a total bother, I just adjusted the shades appropriately for privacy. Kimberly & her family were AMAZINGLY FRIENDLY! My 4yo was invited to meet the children,...
The price is AU$287
includes taxes & fees
14 July - 15 July
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, (14)
"The listing was clean and had everything we needed. Neighborhood was clean and quiet. Host was very responsive and accommodated our stay to our needs. We would recommend this listing to anyone and everyone. There’s a fire pit in the back yard, a deck with a charcoal grill, hot tub was amazing, and we didn’t see any bugs or roaches or creepy crawlers during our entire stay. Hot water and good water pressure!"
Super close to beaches, the historic triangle, and bush gardens!
Williamsburg Campground
2.5 star property
8.0 out of 10, Very good, (15)
"The staff was very friendly and seemed to go out of their way to make sure everything was good with the check in. "
Williamsburg Campground
Chickahominy River Home Close to Williamsburg!
9.6 out of 10, Exceptional, (12)
"The website for the location was a bit confusing especially driving 8hrs+ but the response and overall experience with both property manager and owner, no words can describe, exceptional hospitality! Thank you"
Chickahominy River Home Close to Williamsburg!
The Little Blue Cottage - Topping : Waterfront!
9.8 out of 10, Exceptional, (30)
"We loved our stay here. The property is very clean and well stocked. I really appreciated all the supplies that came with the house, i.e hand soaps, paper towels, etc. Usually small items like these are not provided at rental houses, so this a nice touch for us! We loved the dock and waterviews. It is located in a quiet neighborhood but amenities are close by. If you are looking for a quiet and serene get away this is it! Highly recommend and would 100 percent book again!"
The Little Blue Cottage - Topping : Waterfront!
Vacation Getaway on Chesapeake Bay
9.8 out of 10, Exceptional, (142)
"This location was ideal for our participation in a junior sailing regatta at Fishing Bay Yacht Club! The house was in great condition and provided everything we needed. We enjoyed the back yard and pier overlooking the water. Our family had a lovely time! We’ll be back."
Vacation Getaway on Chesapeake Bay
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (63)
"Nice"
Oceanfront White Stone Cottage w/ Private Beach!
Cozy cottage on the Chesapeake Bay
10.0 out of 10, Exceptional, (26)
"What a sweet place to stay. Perfect for a nice relaxing weekend ."
Cozy cottage on the Chesapeake Bay
Charming Boutique Hotel close to Williams and Mary College
2.0 out of 10, (1)
"No housekeeping service. No microwave. People actually live here. Hard to get help from the front desk when they were around. Half the facility isnt even open."
Charming Boutique Hotel close to Williams and Mary College
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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

Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 star property
8.8 out of 10, Excellent, (2384)
"Amazing! Would definitely stay here again! "
The price is AU$191
includes taxes & fees
10 July - 11 July
Hilton Vacation Club The Historic Powhatan Williamsburg
Best Western Historic Area Inn
2.5 star property
8.0 out of 10, Very good, (1076)
"It was nice. "
The price is AU$160
includes taxes & fees
1 July - 2 July
Best Western Historic Area Inn
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
3.0 star property
8.8 out of 10, Excellent, (1009)
"The hotel is located in a convenient spot when visiting Colonial Williamsburg.The rooms were as expected for an older hotel. The view outside from the room was very calming with beautiful trees! The pool was great! Large and temperature warm enough to just walk in. The breakfast was good! Not cooked to order but prepackaged. Warm breakfast sandwiches fresh fruit bagels and waffles, Only complaint is the restaurant is closed on n Wednesdays.Wasn’t informed when I made reservations."
The price is AU$248
includes taxes & fees
8 July - 9 July
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.

Everything you need to know about Gloucester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gloucester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Gloucester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gloucester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gloucester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gloucester holiday rentals we have selected for you start as low as AU$287 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gloucester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gloucester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gloucester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

How many holiday rentals are there in Gloucester?

Expedia has 21 holiday 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 wider area, you’ll find Rosewell Ruins and Busch Gardens Williamsburg.

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.

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