A steel bridge over a calm river with a sandy beach and rocky outcrops on the right.

Holiday Homes in Gloucester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Gloucester holiday homes

A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

1. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
9.4 out of 10, Exceptional, (34 reviews)
"This is a very comfortable clean home in a nice quiet neighborhood. It’s very close to some excellent restaurants and places of interest. We especially enjoyed the sunroom."
United States
Joseph B.
The price is AU$508
includes taxes & fees
3 Nov - 4 Nov
Radiant Gloucester House w/ Private Porch!
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

2. Nice 3-bedroom house with AC in peaceful Hartfield

Nice 3-bedroom house with AC in peaceful Hartfield
Hartfield
The price is AU$345
includes taxes & fees
25 Oct - 26 Oct
Nice 3-bedroom house with AC in peaceful Hartfield
A large house with multiple decks and a view of a lake.

3. 9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater

9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater
North
8.6 out of 10, Excellent, (14 reviews)
"The house was perfect for my coworkers and I who were in the area for work for a couple days. Jessica was friendly and communicated well. Would recommend for anyone looking for a lot of space to relax in a quiet area."
United States
Jonas M.
The price is AU$2,017
includes taxes & fees
29 Oct - 30 Oct
9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater
A sandy beach path leading to the ocean, surrounded by dry grass.

4. 1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
Mathews
10.0 out of 10, Exceptional, (42 reviews)
"We had a great time at Baydreamin'."
United States
Crystal D.
The price is AU$466
includes taxes & fees
26 Oct - 27 Oct
1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
A dining area with a view of a lake and trees, featuring white tables and benches, ceiling fans, and large windows.

5. RivahMojo on Mill Creek-just off RappahannockRiver

RivahMojo on Mill Creek-just off RappahannockRiver
Topping
10.0 out of 10, Exceptional, (26 reviews)
"Property was lovely, host very responsive, couldn’t ask for more!"
United States
Donna B.
The price is AU$608
includes taxes & fees
28 Oct - 29 Oct
RivahMojo on Mill Creek-just off RappahannockRiver
A covered outdoor area with a metal roof, a small shed, and a concrete patio.

6. Williamsburg Home for Colonial & Theme Park Trips

Williamsburg Home for Colonial & Theme Park Trips
Williamsburg
The price is AU$820
includes taxes & fees
3 Nov - 4 Nov
Williamsburg Home for Colonial & Theme Park Trips
A small, single-story house with a red door, a porch with a white railing, and a number '70' sign.

7. Luxury Studio Guesthouse, Walk to Museum, Boat Parking

Luxury Studio Guesthouse, Walk to Museum, Boat Parking
Deltaville
10.0 out of 10, Exceptional, (61 reviews)
"Awesome little place. We absolutely enjoyed staying here. Very clean and had all amenities one would need. Will definitely book again. "
United States
Stan R.
The price is AU$426
includes taxes & fees
21 Oct - 22 Oct
Luxury Studio Guesthouse, Walk to Museum, Boat Parking
A bright, white interior with a wooden dining table and white chairs. There are windows with curtains, a ceiling fan, and a view of greenery outside.

8. Relaxing Family Cottage w/ Sunroom & Backyard Movie Nights

Relaxing Family Cottage w/ Sunroom & Backyard Movie Nights
Toano
10.0 out of 10, Exceptional, (38 reviews)
"Excellent place to relax and unwind!"
United States
Debra J.
The price is AU$667
includes taxes & fees
21 Oct - 22 Oct
Relaxing Family Cottage w/ Sunroom & Backyard Movie Nights
A modern kitchen with white cabinets, stainless steel appliances, a microwave, a refrigerator, and a sink.

9. The Williamsburg Haven

The Williamsburg Haven
Williamsburg
10.0 out of 10, Exceptional, (29 reviews)
"great place"
United States
Emily J.
The price is AU$433
includes taxes & fees
3 Nov - 4 Nov
The Williamsburg Haven
A wooden picnic table with a pitcher, glasses, and a plate set on a grassy area by a body of water.

10. Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden

Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
Locust Hill
10.0 out of 10, Exceptional, (41 reviews)
"The hosts made sure that everything in the house made one feel comfortable and at home. The view is fantastic and the landscaping with the rose garden and pool on a sunny day is inviting and relaxing. We enjoyed our stay "
United States
Mary S.
The price is AU$749
includes taxes & fees
27 Oct - 28 Oct
Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.

11. The Bungalow, Pool, Dock, Kayaks, & Game Room

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
The price is AU$605
includes taxes & fees
25 Oct - 26 Oct
The Bungalow, Pool, Dock, Kayaks, & Game Room
A modern kitchen with stainless steel appliances, a dining area with a blue sofa, and a small outdoor garden with a waterfall.

12. 8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
North Newport News
10.0 out of 10, Exceptional, (25 reviews)
"This house is stunning! Beautiful home, so clean, convenient to absolutely everything! It deserves way more than 5 stars! "
United States
Amy J.
The price is AU$1,220
includes taxes & fees
27 Oct - 28 Oct
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
A spacious dining area with high wooden tables and chairs, surrounded by shelves filled with decorative items.

13. 1896 Historic Mansion with a general store

1896 Historic Mansion with a general store
North Newport News
10.0 out of 10, Exceptional, (12 reviews)
"Nice accommodations and nice host. Very accommodating."
United States
Jim R.
The price is AU$1,242
includes taxes & fees
27 Oct - 28 Oct
1896 Historic Mansion with a general store
A modern kitchen with white cabinets, stainless steel appliances, and a large island with a sink.

14. 8 Miles to Busch Gardens/Spacious Family Getaway/ 7Bedroom/3 masters /5 Bath

8 Miles to Busch Gardens/Spacious Family Getaway/ 7Bedroom/3 masters /5 Bath
North Newport News
10.0 out of 10, Exceptional, (17 reviews)
"More amenities than expected, very clean and well-kept. "
United States
Swetha P.
The price is AU$1,851
includes taxes & fees
26 Oct - 27 Oct
8 Miles to Busch Gardens/Spacious Family Getaway/ 7Bedroom/3 masters /5 Bath
A bedroom with a bed, bedside tables, a window with curtains, a patterned rug, and a ceiling vent.

15. Belle Haven - High Speed internet, walk to town

Belle Haven - High Speed internet, walk to town
Kilmarnock
10.0 out of 10, Exceptional, (41 reviews)
"Great cottage, beautiful place to stay at"
United States
Darren W.
The price is AU$438
includes taxes & fees
2 Nov - 3 Nov
Belle Haven - High Speed internet, walk to town
A wooden dock with chairs facing a calm lake, surrounded by dense forest.

16. Private home on creek with dock.

Private home on creek with dock.
Lancaster
9.2 out of 10, Wonderful, (15 reviews)
"Great place loved it!"
United States
Brandon W.
The price is AU$297
includes taxes & fees
18 Nov - 19 Nov
Private home on creek with dock.
A small, single-story house with a porch, a wooden deck, and a brick pathway.

17. Deltaville 2BR Retreat, Walk to Museum, Boat Parking

Deltaville 2BR Retreat, Walk to Museum, Boat Parking
Deltaville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was perfect - loved staying here. "
United States
John L.
The price is AU$450
includes taxes & fees
8 Nov - 9 Nov
Deltaville 2BR Retreat, Walk to Museum, Boat Parking
A red cabin with a porch, surrounded by trees.

18. 4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Lanexa
10.0 out of 10, Exceptional, (10 reviews)
"The house was beautiful. Everything was perfect, we could not be happier with our stay."
United States
Kimberly L.
The price is AU$1,007
includes taxes & fees
30 Oct - 31 Oct
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
A beach with a sandy shore, a water body, and a few people.

19. Family friendly 5 bedroom home within Walking distance To CNU

Family friendly 5 bedroom home within Walking distance To CNU
Central Newport News
10.0 out of 10, Exceptional, (58 reviews)
"The property is very well maintained and clean. Ample parking for multiple cars. The host is a great communicator and available to answer any questions you may have."
United States
Anonymous traveller
The price is AU$1,303
includes taxes & fees
28 Oct - 29 Oct
Family friendly 5 bedroom home within Walking distance To CNU
A small, single-story house with a porch, a wooden deck, and a brick pathway.

20. Two Private Cottages 3BR, Boat Parking, Walk to Marinas

Two Private Cottages 3BR, Boat Parking, Walk to Marinas
Deltaville
10.0 out of 10, Exceptional, (1 review)
"Clean house, comfy"
United States
Ellen M.
The price is AU$721
includes taxes & fees
21 Oct - 22 Oct
Two Private Cottages 3BR, Boat Parking, Walk to Marinas
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gloucester Hotel Reviews

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

10/10 Excellent
"The best value for the price. Very clean and wonderfully organized. Going back later this year to Williamsburg and will surely be booking here again."
Wesley 2-night trip
Posted 2 hours ago
King’s Creek Resort by Spinnaker

Find out more about Gloucester

Gloucester Holiday Homes information

Number of reviews
525
Accommodation
320 Holiday Homes
Lowest Price
AU$297
Highest Price
AU$2,017

Explore a world of travel with Expedia