Gloucester Holiday Rentals

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Holiday Rentals in Gloucester

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, (13)
"Our stay was great! The host gave us all the information we needed, and the property was amazing. We spent plenty of time talking and reading out on the water while enjoying the view. This property is quiet and fairly secluded but also doesn't feel far from food and entertainment. We loved our stay and would recommend this location to anyone!"
The price is NZ$508
includes taxes & fees
3 Jun - 4 Jun
Welcome to this Waterfront Home with Amazing Views
Property grounds
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
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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!
View from property
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
10.0 out of 10, Exceptional, (12)
"Clean and very nice."
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
Private kitchen
Super close to beaches, the historic triangle, and bush gardens!
8.0 out of 10, Very good, (13)
"Beds were comfortable, jacuzzi and large shower in the Master Bedroom was a plus! Kitchen was very functional as we stayed in for breakfast each morning. We enjoyed our stay and would stay here again in the future! Just wished we had better weather during our visit (rained all weekend)!"
Super close to beaches, the historic triangle, and bush gardens!
Property grounds
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (27)
"Large family group of 24 gathered for weekend food and fun around CNU graduation. We loved the house, location and appreciated all the owner support and communication. We could not have asked for better amenities.Highly recommend!"
Private 5-acre Waterfront Peninsula with Beach
Fridge, microwave, oven, stovetop
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
9.4 out of 10, Exceptional, (106)
"We all - seniors to toddlers - enjoyed our stay here! Wonderful to be on the river, and also convenient to Williamsburg!"
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Property grounds
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.8 out of 10, Exceptional, (103)
"Nice stay within a beautiful gated community- out of the hustle & bustle of the tourist area but conveniently located. We enjoyed the Italian restaurant nearby - Maurizio’s! Beds & bedding very comfortable!! Good communication with owners."
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, (39)
"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.
Exterior
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (303)
"Spectacular location. Unbelievable views. Extremely well appointed house."
Cottage on a Private Island in the York River
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, (123)
"Perfect little getaway. Very quaint. Calm and peaceful. Very friendly community."
The price is NZ$345
includes taxes & fees
30 May - 31 May
NO CHILDREN UNDER 5.. Smoking outside with doors and windows closed. No animals.
Property grounds
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (62)
"Nice"
Oceanfront White Stone Cottage w/ Private Beach!
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (113)
"Pet friendly well kept property with more amenities than others we’ve stayed in when it comes to outdoor activities, kitchen supplies/gadgets to the outdoor dog bowl. Quiet and private location with nice views from porches and even inside. We enjoyed our stay and so did our pups. 1 day with bad weather and it didn’t matter we had movie marathon and a great view. Some hunting dogs would come visit and make our girls wonder further than normal but zero complaints otherwise. Premium beds and...
Private, 7-acre waterfront retreat on Winter Harbor Haven
Private kitchen
Cozy Marina Home, Pet Friendly, Free Parking, huge yard for pets and boats
8.6 out of 10, Excellent, (7)
"Cute cottage in a great location! It is a great place to take your furry family members due to the large back yard and friendly neighborhood. I will return on my next visit to see my daughter in her apprenticeship! Thankful for the friendly, responsive host!"
Cozy Marina Home, Pet Friendly, Free Parking, huge yard for pets and boats
Log Cabin at Anvil Campground
Anvil Campground
2.5 star property
8.4 out of 10, Very good, (33)
"This is a real gem. It is small but very accomodating. Love seeing the families enjoy themselves and seeing everyone walking their dogs. Very friebdly. Wish it hadn’t rain but our daughter still had a great time at the game room and the free ice cream. Wish the ac worked better in the game room amd bathrooms but they were not terrible so I still give them a good review. We stayed in the apprentice cabin and it was very nice and comfortable-exept the queen bed could have used a spring base...
The price is NZ$185
includes taxes & fees
30 May - 31 May
Anvil Campground
Property grounds
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!
9.6 out of 10, Exceptional, (14)
"Cannot beat this location. The private beach was just incredible. We came with two dogs who enjoyed going for a swim each morning. The kids loved hanging out on the beach all day. The hosts were responsive and thoughtful. When we arrived the first night the lights were on and music was gently playing. Thoughtful touches that were very much appreciated. We could not have hoped for a better experience."
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!
Aerial view
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
9.6 out of 10, Exceptional, (37)
"Had a great stay, with little to no complaints!"
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
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
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
10.0 out of 10, Exceptional, (179)
"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 w Private Beach, Pets Ok-2 Weeks in Aug Open!
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

Exterior
Holiday Inn Express Gloucester, an IHG Hotel
3.5 star property
7.2 out of 10, Good, (512)
"Nice people great place very clean"
The price is NZ$206
includes taxes & fees
9 Jun - 10 Jun
Holiday Inn Express Gloucester, an IHG Hotel
View from property
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
10.0 out of 10, Exceptional, (12)
"Clean and very nice."
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
Indoor pool, outdoor pool, pool umbrellas, pool loungers
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 star property
8.8 out of 10, Excellent, (2361)
"Units are like apartments versus a room at hotel.full size kitchen saves money versus going out for every meal. Close to outlet mall and other shopping. Within a few minutes to many restaurants. Adult only pool and hot tub outside. They also have 2 family pools."
The price is NZ$217
includes taxes & fees
6 Jun - 7 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gloucester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gloucester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gloucester. Seeing all the best attractions is bound to make you fall in love with Gloucester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gloucester short-term rentals, that won’t be hard to do.

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.

Recent reviews of Gloucester properties
Expedia verified reviews