Gloucester Vacation Rentals

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Vacation Rentals in Gloucester

Radiant Gloucester House w/ Private Porch!
9.8 out of 10, Exceptional, 11 reviews
"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!
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, 65 reviews
"We had a wonderful time. The cottage was adorable, with every little detail thought of. Wish we had more time to explore the area. Thanks for sharing this special place with others."
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, 14 reviews
"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 CA $204
CA $434 total
includes taxes & fees
Jun 9 - Jun 10
Welcome to this Waterfront Home with Amazing Views
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Beautiful & Peaceful House Overlooking the River. Pets Welcome!
10.0 out of 10, Exceptional, 12 reviews
"Clean and very nice."
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, 242 reviews
"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
Super close to beaches, the historic triangle, and bush gardens!
8.2 out of 10, Very good, 14 reviews
"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!
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
9.4 out of 10, Exceptional, 106 reviews
"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.
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.8 out of 10, Exceptional, 103 reviews
"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!
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, 303 reviews
"Spectacular location. Unbelievable views. Extremely well appointed house."
Cottage on a Private Island in the York River
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
9.6 out of 10, Exceptional, 37 reviews
"Had a great stay, with little to no complaints!"
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, 27 reviews
"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
NO CHILDREN UNDER 5.. Smoking outside with doors and windows closed. No animals.
10.0 out of 10, Exceptional, 124 reviews
"We did nothing but relax here! The three decks were our favorite places!"
The price is CA $238
CA $286 total
includes taxes & fees
Jun 11 - Jun 12
NO CHILDREN UNDER 5.. Smoking outside with doors and windows closed. No animals.
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, 3 reviews
"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 CA $155
CA $297 total
includes taxes & fees
Jun 5 - Jun 6
Hampton Centrally Located Oasis
Anvil Campground
2.5 star property
8.4 out of 10, Very good, 33 reviews
"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 CA $143
CA $163 total
includes taxes & fees
Jun 5 - Jun 6
Anvil Campground
Mobjack Bay Rental on Private Cove!
10.0 out of 10, Exceptional, 2 reviews
"The home was very comfortable and very peaceful. The amenities were wonderful! Very clean. The owner was responsive and kind. We would come back every time!"
Mobjack Bay Rental on Private Cove!
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, 62 reviews
"Nice"
Oceanfront White Stone Cottage w/ Private Beach!
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, 113 reviews
"This is a great place to kayak and get away from city noise! You hear only the wildlife, hunting dogs raised by the neighbor, and a few fishing boats. The house is well stocked, a back up of paper supplies such as toilet paper and paper towels would be helpful. We spent the majority of our time on the screened-in porch in the rocking chairs and at the picnic table - amazing! The afternoon sun hits the other side of the house, so you can enjoy the porch all day long! I would agree with a...
Private, 7-acre waterfront retreat on Winter Harbor Haven
Cozy Marina Home, Pet Friendly, Free Parking, huge yard for pets and boats
8.6 out of 10, Excellent, 7 reviews
"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
Charming Boutique Hotel close to Williams and Mary College
2.0 out of 10, 1 review
"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
Restored 1920's Cottage on 1 Acre w/ Fire Pit
9.4 out of 10, Exceptional, 44 reviews
"Our grandchildren came for several visits and overnights. It was great. The cottage is very user friendly and was quiet. The surrounding areas uncluding paddock was a bonus for our Shetland sheepdogs. The walking trails were fine. We had a fantastic stay."
Restored 1920's Cottage on 1 Acre w/ Fire Pit
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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

Holiday Inn Express Gloucester, an IHG Hotel
3.5 star property
7.2 out of 10, Good, 513 reviews
"Very nice staff "
The price is CA $144
CA $161 total
includes taxes & fees
Jun 12 - Jun 13
Holiday Inn Express Gloucester, an IHG Hotel
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 star property
8.8 out of 10, Excellent, 2,380 reviews
"Nice clean and safe place to stay. I would definitely recommend "
The price is CA $143
CA $201 total
includes taxes & fees
Jun 6 - Jun 7
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, 1,014 reviews
"Great value when you package the stay with a ticket to Colonial Williamsburg. Breakfast was hectic as everyone is jostling to obtain food. The room is fine except the mattress was not comfortable."
The price is CA $183
CA $229 total
includes taxes & fees
Jun 5 - Jun 6
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.

Recent reviews of Gloucester properties
Expedia verified reviews