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Compare 323 Vacation Homes in Gloucester with updated reviews, rates, and availability.

The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
10.0 out of 10, Exceptional, 23 reviews
"We had a wonderful stay. Necessary things were provided for us, and the beautiful surroundings made our stay very relaxing and fun. I highly recommend this as a vacation destination for your family."
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
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
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, 4 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 $114
$215 total
includes taxes & fees
Jun 26 - Jun 27
Hampton Centrally Located Oasis
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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!
Waterfront Topping Vacation Home w/ Boat Dock!
10.0 out of 10, Exceptional, 6 reviews
"Great place to unwind, relax, spend quality with the family. Bill’s “Rivah house” was clean and has all the essentials we needed for a great weekend. Enjoyed hanging out on the deck, fishing and crabbing on the dock, and kayaking! Bill is great host and communicated with us early, Hope to come back soon!"
Waterfront Topping Vacation Home w/ Boat Dock!
Wyndham Kingsgate - 2 Bedroom Deluxe
9.0 out of 10, Wonderful, 6 reviews
"The unit is nice and great for a family to have their own rooms. I did not realize it was on the third floor (did not see it mentioned) and wished I had known due to difficulties with stairs. The beds were comfy, and everything was nice. We did not use any of the amenities (pool, cinema, etc) but they seemed to have a lot to offer. Was not a fan of the timeshare push. I even told them the owners names and they still pushed. After a four hour drive, I just wanted to get to the condo and start our...
Wyndham Kingsgate - 2 Bedroom Deluxe
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
9.4 out of 10, Exceptional, 107 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.
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, 65 reviews
"Beautiful Virginia countryside neighborhood surrounds this lovely cottage. A great get away."
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
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!
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
Chickahominy River Home Close to Williamsburg
9.6 out of 10, Exceptional, 11 reviews
"The host was very gracious. Upper area very quaint and nicely decorated. Lower area also very nice to stay or use just for play. Very quiet Enjoyed very much"
Chickahominy River Home Close to Williamsburg
Radiant Gloucester House w/ Private Porch!
9.8 out of 10, Exceptional, 12 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!
Walk to Town Restaurants. 1st floor King Bed & Walk in Shower! Fire Pit🔥!
10.0 out of 10, Exceptional, 22 reviews
"We came to the area for our granddaughter’s graduation and it was only minutes from the high school. It was in close proximity to quite a few good restaurants and downtown Mathews! The host was quick to reply to any questions or comments that we had. If the opportunity presented itself, we would definitely stay here again!"
The price is $169
$336 total
includes taxes & fees
Jul 14 - Jul 15
Walk to Town Restaurants. 1st floor King Bed & Walk in Shower! Fire Pit🔥!
Monthly discount- beautiful house, Gloucester VA
10.0 out of 10, Exceptional, 13 reviews
"We visit the area a lot to see family so I've stayed in quite a few rentals here. This is my first time at this property and I would stay again. Looks just like the listing. I appreciate the simple layout for our needs. 3 bedrooms meant we were comfortable at night. I thought the one king bed was pretty soft and the other firm; both comfy just think that's helpful to some to know. The living area and kitchen/dining space aren't huge but again you should know that from the pictures and it worked...
Monthly discount- beautiful house, Gloucester VA
Mid-century modern meets classic cape on the coast.
10.0 out of 10, Exceptional, 4 reviews
"Very comfortable setting. Good location for nearby venues. Enjoyed our stay."
Mid-century modern meets classic cape on the coast.
Beach House on Chesapeake Bay!
10.0 out of 10, Exceptional, 111 reviews
"Everything was perfect!"
Beach House on Chesapeake Bay!
Waterfront, Private Dock, Fire Pit, Hot Tub, Screened Porch and Beach Access!
10.0 out of 10, Exceptional, 23 reviews
"Sip Into Sunset was a wonderful getaway! The cottage is well-stocked with just about everything you could imagine needing (except ice- bring that!) and the sunsets were *amazing*! The list of "favorite features" includes fenced yard for dogs, well-stocked kitchen and bar, comfy beds, lots of great places to hang out and enjoy the view- dock, screened porch, sunroom. Best memory is catching blue crabs off the dock on our last day and enjoying them for happy hour. Was a wonderful visit and we will...
Waterfront, Private Dock, Fire Pit, Hot Tub, Screened Porch and Beach Access!
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve
10.0 out of 10, Exceptional, 118 reviews
"The house is absolutely magical. It’s like stepping back in time. So many incredible details. The owners put so much time and energy into restoring it. It was such a special part of our visit to historic Williamsburg. I feel lucky we found it."
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve
Centrally Located Hampton Home: 6 Mi to Downtown!
9.0 out of 10, Wonderful, 4 reviews
"Great location and close to the coliseum. Host was pleasent and on top of communication. No major issues for the house but could use the items below improvement: 1. Kitchen was well equiped but somehow was missing a cutting board. 2. The mattress that is in the bedroom on the left when going down the hall is very uncomfortable and the individual sleeping there decided to sleep on the couch instead. On the other hand, the couch is VERY comfortable! Everything else was fantastic and i would...
Centrally Located Hampton Home: 6 Mi to Downtown!
Colonial Brick Home Nestled in the Woods.
4.0 star property
9.4 out of 10, Exceptional, 8 reviews
"Golf trip with the dogs. Quiet, comfortable and great value. Cant say enough about the clear and timely communication with the property host. Will definitely come back next year. This VRBO wont disappoint. Thank you for an amazing stay."
Colonial Brick Home Nestled in the Woods.
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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 property types in Gloucester

"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, 65 reviews
"Beautiful Virginia countryside neighborhood surrounds this lovely cottage. A great get away."
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Radiant Gloucester House w/ Private Porch!
9.8 out of 10, Exceptional, 12 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!
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!
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.

Gloucester Vacation Homes information

Number of reviews
548
Accommodation
323 Vacation Homes
Lowest Price
$114
Highest Price
$169

Recent reviews of Gloucester hotels
Expedia verified reviews