Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Colonial Brick Home Nestled in the Woods.
4.0 star property
9.8 out of 10, Exceptional, (17)
"The picture of this place does not do it justice. It is so clean inside and spacious for everyone to move around and be really comfortable. Easy to get to restaurants and shopping just six minutes away. Water park and Busch gardens very close as well. The staff response time is really great we appreciate all the help. My kids and family really loved it. If we come back to VA we will definitely be back. "
The price is AU$695
includes taxes & fees
15 Oct - 16 Oct
Colonial Brick Home Nestled in the Woods.
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (79)
"This little cottage is filled with thoughtful touches inside and out. The beds were super comfortable. Everything was bright and clean. The neighborhood was quiet and the people friendly. Outstanding in every way. We highly recommend the BeeHaven cottage."
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Vacation to remember! Huge family-sized townhouse for 12 near all attractions.
9.8 out of 10, Exceptional, (24)
"Great stay. Great home and amenities. Great location. Lots to do!"
Vacation to remember! Huge family-sized townhouse for 12 near all attractions.
Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, (17)
"Very nice home. Beautiful dock. Great location. Very clean."
The price is AU$556
includes taxes & fees
1 Oct - 2 Oct
Welcome to this Waterfront Home with Amazing Views
Radiant Gloucester House w/ Private Porch!
9.4 out of 10, Exceptional, (13)
"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!
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
9.8 out of 10, Exceptional, (153)
"We really enjoyed our stay at the Little Blue House. The location could not have been better -- in walking distance to the Tides Inn, the Local, and a few cute shops. There was more to see and do just a short drive away. The house itself was very cute and my daughter loved having her own room and bathroom. The streaming options (Netflix, Hulu, etc.) didn't work, but I think they just need to be upgraded. The jacuzzi jets in the big tub were TO DIE FOR. We highly recommend!"
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
10.0 out of 10, Exceptional, (36)
"We loved our stay at the Green House at Green Springs! We found it to be very clean, spacious and welcoming. The pool area was exceptional. Though it is out away from the city, it is still close to everything there is to see and do in the Williamsburg area. Our stay was even better than we anticipated and we hope to return on our next visit to the area! Very pet friendly too and our pups enjoyed their stay, as well!"
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
Family sized resort townhouse sleeps 12. Great amenities. Near attractions.
9.4 out of 10, Exceptional, (29)
"The property and accommenation were just on point. Enjoyed the complete stay and the pools were unbelievable. Would do this again."
Family sized resort townhouse sleeps 12. Great amenities. Near attractions.
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (32)
"There were so many things to do at this beautiful location! We enjoyed boating, swimming, crabbing, disc golf, bonfires, games, and more! The house comfortably sleeps 21 people! It’s a lovely house that has an incredible view and it’s so quiet and relaxing. "
The price is AU$1,219
includes taxes & fees
1 Oct - 2 Oct
Private 5-acre Waterfront Peninsula with Beach
Vacation Getaway on Chesapeake Bay
10.0 out of 10, Exceptional, (151)
"This house is truly in a perfect special spot. Super close to a few good spots to eat, and so jam packed with nature. So much nicer in person than even advertised in the pictures. Frank and Sandy couldn’t have been easier to deal with and the house was great. Kids enjoyed the heck out of the creek. Would love to visit again. "
Vacation Getaway on Chesapeake Bay
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.
10.0 out of 10, Exceptional, (8)
"This place was top notch! Love the property, the place was very spacious and all that I had hoped for. The owner was very attentive and responded immediately to all of my questions. I will absolutely book here again!"
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
10.0 out of 10, Exceptional, (144)
"Peaceful setting wonderful views. Location is wonderful. Excellent!"
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
Come for a break, stay for the fun in Williamsburg!
9.6 out of 10, Exceptional, (5)
"Clean, neat, lots of room. Host was super responsive and easy to work with. Would def stay again if I’m in that area!"
Come for a break, stay for the fun in Williamsburg!
Creekside Cottage Retreat with HotTub!
10.0 out of 10, Exceptional, (15)
"We thoroughly enjoyed our stay on the Creek. We rented the creek house out for my dad's 72nd birthday. He loves to fish and he had an amazing time here. The house was very well kept and the walk down to the creek was very simple and enjoyable. My father just had a hip replaced a month ago and had no problems walking down to fish. He caught a lot of large catfish on liver and a cork, many small white bass and perch on jigs and a small largemouth bass on white spinner bait. We didn't use the...
Creekside Cottage Retreat with HotTub!
Quiet Bayfront Hayes Home w/ Deck + Private Beach!
10.0 out of 10, Exceptional, (11)
"Great place - khaki was a hit. Remember to bring bug spray gnats can be a problem by the water. Stay was fun and relaxing. Quiet area. Close to all parks - "
Quiet Bayfront Hayes Home w/ Deck + Private Beach!
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, (12)
"A lovely little house located in the heart of Hampton. We couldn't have asked for a better place to stay and really appreciated the hospitality of the host (Thank you Christina!)."
The price is AU$318
includes taxes & fees
1 Oct - 2 Oct
Hampton Centrally Located Oasis
Super close to beaches, the historic triangle, and bush gardens!
8.2 out of 10, Very good, (20)
"Beautiful house and having the hot tube was a plus "
Super close to beaches, the historic triangle, and bush gardens!
Fantastic waterfront home on Jackson Creek
10.0 out of 10, Exceptional, (48)
"Great"
Fantastic waterfront home on Jackson Creek
Charming 2 bed 1 bath near Langley Air Force Base
10.0 out of 10, Exceptional, (28)
"This property was perfect for our needs. Darling house with charm and convenience. Clean and well stocked. We loved our stay!"
Charming 2 bed 1 bath near Langley Air Force Base
Little Bay Waterfront Retreat
9.6 out of 10, Exceptional, (55)
"We wanted somewhere where we could have a private beach to swim with our dog, and enjoy the wonderful view of the bay. This fit the bill perfectly! The water was warm, and the waves were minimal, making it a wonderful afternoon of swimming enjoyment. The house is spacious and has everything you could want or need. Just sitting in the sunroom in the morning with your coffed is worth the price alone! Highly recommended!!"
Little Bay Waterfront Retreat
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Other property types in Gloucester

"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (79)
"This little cottage is filled with thoughtful touches inside and out. The beds were super comfortable. Everything was bright and clean. The neighborhood was quiet and the people friendly. Outstanding in every way. We highly recommend the BeeHaven cottage."
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock
10.0 out of 10, Exceptional, (18)
"I was absolutely pleasantly surprised how beautiful this home was. A lot of antique pieces was a thrill for me to see, and the dining room table...whew! It was such a lovely piece! We had plenty of room so we didn't feel cramped. The bed upstairs was definitely more comfortable than my own at home. We definitely didn't want to leave, and hooe to be back!"
Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (252)
"Nice and peaceful cottage! Found everything we needed and more. Thank you for hosting us. "
Historic Cottage on Ware River Estate
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.