Gloucester Vacation Rentals

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Browse Select Gloucester Vacation Homes

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 CA $156
CA $298 total
includes taxes & fees
May 28 - May 29
Hampton Centrally Located Oasis
Terrace/patio
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
9.8 out of 10, Exceptional, (147)
"Wonderful home with everything you could need available. The owners were very interested in our comfort and were very helpful. The home is located in a quiet location accessible to restaurants and shopping."
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
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
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Smart TV, books
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
9.8 out of 10, Exceptional, (19)
"Really enjoyed this property! Jill welcomed us with a lovely bouquet in the kitchen which is well stocked with good appliances, utensils, paper towels and lots of room. The sun room opens onto the patio area around the pool with three different seating areas, tables and a fire pit. This home is close to Williamsburg, Jamestown and Yorktown. The area has several good restaurants and grocery stores. It was quite a perfect setup for us!"
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
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 CA $811
CA $1,938 total
includes taxes & fees
Jun 8 - Jun 9
Private 5-acre Waterfront Peninsula with Beach
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (111)
"Beautiful home. Very well equipped."
Private, 7-acre waterfront retreat on Winter Harbor Haven
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
Property grounds
Sojourn Aviators Dream on Back River
10.0 out of 10, Exceptional, (7)
"4 sisters getting together to laugh and reminisce. We had a blast. The house was great and met our every need."
The price is CA $265
CA $646 total
includes taxes & fees
Jun 5 - Jun 6
Sojourn Aviators Dream on Back River
Golf
Water front, river views, fishing from backyard, Large yard to enjoy.
9.4 out of 10, Exceptional, (16)
"Great stay and lovely hosts!"
Water front, river views, fishing from backyard, Large yard to enjoy.
Children's area
Special Holiday Rates. 4BDR townhouse (12) in Historic Powhatan 💕
8.8 out of 10, Excellent, (5)
"The property was just as described. The entire party commented on how much room we had. Easy to get to all Williamsburg attractions. I would rent again."
Special Holiday Rates. 4BDR townhouse (12) in Historic Powhatan 💕
Interior
Charming Boutique Hotel close to Williams and Mary College
2.0 out of 10, (1)
"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
Interior
Amazing views of the Chesapeake Bay.
10.0 out of 10, Exceptional, (10)
"We were in town for a reunion with good friends and former neighbors. This cottage was perfect for our needs! Spacious and comfortable. Kitchen stocked with everything you might need. Great view of the river and a covered front porch to sit and enjoy it! Lovely area to walk around as well. Host very responsive! I would definitely stay here again. Highly recommend!"
Amazing views of the Chesapeake Bay.
Exterior
Tranquility on the Water! Renovated Modern Farmhouse on Private Cove on N. River
9.8 out of 10, Exceptional, (61)
"I met up with a good friend for a long weekend that immediately felt too short. The house is absolutely wonderful! Views galore. Total peace and tranquility. Very private. We just wanted to enjoy the cove, drink coffee by the water and enjoy excursions to Gloucester, Gwynn Island, and Mathews. The house was perfectly located but was wonderful just one its own. We hope to come back soon and take out the kayaks in the warmer weather."
Tranquility on the Water! Renovated Modern Farmhouse on Private Cove on N. River
3 bedrooms, iron/ironing board, WiFi, bed sheets
Vacation Getaway on Chesapeake Bay
10.0 out of 10, Exceptional, (138)
"The house is always immaculate and the amenities are great. The host is the best. The location can't be beat."
Vacation Getaway on Chesapeake Bay
Smart TV, fireplace
5BR home near BuschGardens & CNU/Pool Table
6.4 out of 10, (6)
"GENERAL DESCRIPTION If you are looking for a clean house in a quiet neighborhood where a lot of people may stay overnight with good showers and comfortable beds - this definitely works. It is a large — albeit very basic — house that is most definitely a full-time rental property. PROs Very Clean Quiet neighborhood Roku TVs throughout the house — including big screen in the living room Great communication with manager Short 3-5 minute drive to every box store Comfortable beds Great water...
5BR home near BuschGardens & CNU/Pool Table
Exterior
New! 5 Luxury Bath home w/ modern Chef's Kitchen
9.6 out of 10, Exceptional, (20)
"Beautiful, clean, we love our stay"
New! 5 Luxury Bath home w/ modern Chef's Kitchen
Sun loungers, beach towels
Walk to Town. 1st floor King Bed & Walk in Shower! Charming Remodel. Fire Pit🔥!
10.0 out of 10, Exceptional, (21)
"We had a nice, comfortable stay in Mathews. Our daughter graduated from USCG BM A School in Yorktown, about 35min from this property. She stayed one night with us, along with my husband, my father in law, two teens and two dogs. The house is very dog friendly with supplies and a big yard. Clean, comfortable place to hang out! Awesome communication with host! Great breakfast at Howard-Dooley Cafe just a few minutes away."
The price is CA $171
CA $378 total
includes taxes & fees
May 21 - May 22
Walk to Town. 1st floor King Bed & Walk in Shower! Charming Remodel. Fire Pit🔥!
Fridge, microwave, stovetop, dishwasher
Waterfront Topping Vacation Home w/ Boat Dock!
10.0 out of 10, Exceptional, (5)
"Very much enjoyed our stay!! Great views and great location. Don’t forget to play ping pong in the garage!"
Waterfront Topping Vacation Home w/ Boat Dock!
Exterior
Steps away from Gloucester Marina & Restaurant
10.0 out of 10, Exceptional, (19)
"Our company was working on a project in the Yorktown area. We needed a comfortable house to accommodate our employees for the duration. This house filled all the needs. The guys loved the house. Wonderful property and great property manager. If you need a place in this area, I highly recommend this property!"
Steps away from Gloucester Marina & Restaurant
Indoor pool, outdoor pool
Vacation to remember! Huge family-sized townhouse for 12 near all attractions.
10.0 out of 10, Exceptional, (16)
"This property was perfect for our whole family to enjoy Williamsburg/ ( about 10-15 minutes easy drive ) . Plus close to food store etc and a great playground you can drive to. We had both units upstairs and down and the space was great for our group of12 . ( age range 78- 3 months ). The kids enjoyed indoor pool , mini golf and playground. Highly recommend ."
Vacation to remember! Huge family-sized townhouse for 12 near all attractions.
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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

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 CA $205
CA $435 total
includes taxes & fees
May 20 - May 21
Welcome to this Waterfront Home with Amazing Views
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.