Gloucester Vacation Rentals

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Vacation Rentals in Gloucester

Property grounds
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (241)
"Excellent base for exploring Williamsburg, Yorktown and Jamestown. Beautiful historic cottage on expansive grounds. Dead quiet."
Historic Cottage on Ware River Estate
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, (11)
"Thank you so much for sharing this rental. My family loved being on the water and all were just overwhelmed by the rental. All have rented VRBOs before and all remarked how clean. Also appreciated the good basket, area information and check-out list. As the relative who rented the property, the owners were very responsive to my questions. I'll rent again for family."
The price is $150
$315 total
includes taxes & fees
May 20 - May 21
Welcome to this Waterfront Home with Amazing Views
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View from property
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed the views and experience of Chesapeake Bay as a family. The natural surroundings of the bay spoke to my need to connect with nature, US history, my family, and my partner. The house was accommodating and well kept which was much appreciated for a family such as ours that is extended, loves to spend time, and cook together. We had all of the luxuries of feeling at home but being away all the same, with the space we all needed for comfort. I would recommend this house for the...
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
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!
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, (122)
"Yeah... relaxing"
The price is $175
$212 total
includes taxes & fees
May 15 - May 16
NO CHILDREN UNDER 5.. Smoking outside with doors and windows closed. No animals.
Property grounds
Private 5-acre Waterfront Peninsula with Beach
9.6 out of 10, Exceptional, (25)
"We had a great time staying here and will certainly look to stay again in the future! 5 stars!"
The price is $593
$1,418 total
includes taxes & fees
Jun 8 - Jun 9
Private 5-acre Waterfront Peninsula with Beach
Exterior
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (302)
"We had a very enjoyable stay. Peaceful, quiet, tranquil. Thoroughly enjoyed it. Met with longtime friends for a getaway. The place isn't fancy, but we weren't looking for fancy, just a quiet hideout. Would stay again."
Cottage on a Private Island in the York River
Fridge, microwave, oven, stovetop
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, (3)
"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 $114
$217 total
includes taxes & fees
May 15 - May 16
Hampton Centrally Located Oasis
Property grounds
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.8 out of 10, Exceptional, (102)
"The unit was very nice and perfect for what we needed. Cute community with scenic grounds and plenty of food options nearby. Check in was easy and check out time was generous. It was a perfect centrally located spot for us to do some regional college visits! Would definitely stay here again when we come back for Busch Gardens."
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
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.
Exterior
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!
Private kitchen
Cozy Marina Home, Pet Friendly, Free Parking, huge yard for pets and boats
8.4 out of 10, Very Good, (6)
"Absolutely delighted to share my glowing review of my recent stay here. From start to finish, the experience was nothing short of exceptional. First and foremost, let me commend the host for their outstanding hospitality. They went above and beyond to ensure that every aspect of our stay was comfortable and enjoyable. From prompt communication to thoughtful gestures, such as providing recommendations for local attractions and ensuring the house was well-equipped with everything we needed, their...
Cozy Marina Home, Pet Friendly, Free Parking, huge yard for pets and boats
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!
Log Cabin at Anvil Campground | Blackout drapes, iron/ironing board, free WiFi
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 $100
$114 total
includes taxes & fees
May 15 - May 16
Anvil Campground
Outdoor spa tub
Enjoy family fun and Sunsets at Piankatank Point.
9.8 out of 10, Exceptional, (38)
"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.
Property grounds
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (60)
"This was the most amazing weekend we have had at a VRBO property! The location is absolutely unbeatable and the cottage is brimming with character and ambiance. We loved every minute of our stay and will definitely return. This property is a gem and we feel so blessed to have found this listing."
Oceanfront White Stone Cottage w/ Private Beach!
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
Fridge, microwave, oven, stovetop
Luxurious 3 Bedroom Condo Sleeps 8!
10.0 out of 10, Exceptional, (76)
"Kingsmill Resort was a beautiful setting. The location was great - very close to major attractions. The condo was very clean with comfortable, lovely furnishings. The en suite bedrooms and common area were a perfect fit for our 3 adult couples. The kitchen was well stocked and we appreciated the complimentary coffee. The host was responsive and friendly. I highly recommend this unit for a very pleasant stay."
Luxurious 3 Bedroom Condo Sleeps 8!
Beach nearby, beach towels
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
10.0 out of 10, Exceptional, (119)
"Comfortable, clean and the location was great."
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
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, (508)
"The room was a good size very spacious. I did find dirty linen in the bathroom. And the ac was crazy. It makes a weird sound off and on then cuts off "
Holiday Inn Express Gloucester, an IHG Hotel
View from property
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed the views and experience of Chesapeake Bay as a family. The natural surroundings of the bay spoke to my need to connect with nature, US history, my family, and my partner. The house was accommodating and well kept which was much appreciated for a family such as ours that is extended, loves to spend time, and cook together. We had all of the luxuries of feeling at home but being away all the same, with the space we all needed for comfort. I would recommend this house for the...
Beautiful & Peaceful House Overlooking the River. Pets Welcome!
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Vacation Village At Williamsburg
3.0 star property
8.6 out of 10, Excellent, (1002)
"This was a last minute trip with my family on Mother's Day weekend! The property was wonderful. The room was amazing for the cost. Spacious. The staff was friendly. The room and grounds had everything we needed. Only thing is that it's a little farther Way from Busch Gardens than we thought, but that has nothing to do with the grounds. We will stay longer next.time "
The price is $217
$255 total
includes taxes & fees
May 16 - May 17
Vacation Village At 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.

Everything you need to know about Gloucester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gloucester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Gloucester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $100 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester vacation 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 vacation.

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 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

Club Wyndham Kingsgate

Club Wyndham Kingsgate

5/5 Excellent
"It was an awesome experience "
A verified traveler stayed at Club Wyndham Kingsgate
Posted 3 hours ago
Club Wyndham Kingsgate