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

Search Vacation 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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Gloucester holiday homes

Sun-loungers, beach towels

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, (38 reviews)
"The house was cozy, clean, and welcoming. Would definitely recommend! Rooms were all very spacious. "
United States
Casey J.
The price is HK$1,235
HK$2,763 total
includes taxes & fees
26 Jul - 27 Jul
1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
Microwave, oven, stovetop, dishwasher

Affordable Cottage!

Affordable Cottage!
Deltaville
10.0 out of 10, Exceptional, (2 reviews)
"Clean rooms and comfortable beds, very quiet area! "
United States
Jessica T.
The price is HK$1,100
HK$2,614 total
includes taxes & fees
26 Jul - 27 Jul
Affordable Cottage!
Outdoor dining

Family Friendly Waterfront Home - Private Dock, Kayaks, Fire Pit, Grill, Deck

Family Friendly Waterfront Home - Private Dock, Kayaks, Fire Pit, Grill, Deck
Topping
9.6 out of 10, Exceptional, (11 reviews)
"The stay was very nice!"
United States
Robert H.
The price is HK$3,489
HK$6,313 total
includes taxes & fees
9 Aug - 10 Aug
Family Friendly Waterfront Home - Private Dock, Kayaks, Fire Pit, Grill, Deck
Interior

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, (23 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 HK$5,132
HK$7,577 total
includes taxes & fees
28 Jul - 29 Jul
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
Property grounds

The Williamsburg Haven

The Williamsburg Haven
Williamsburg
10.0 out of 10, Exceptional, (20 reviews)
"Clean convenience easy"
United States
Gavin A.
The price is HK$1,505
HK$1,948 total
includes taxes & fees
28 Jul - 29 Jul
The Williamsburg Haven
Pool

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

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
The price is HK$1,850
HK$3,468 total
includes taxes & fees
30 Jul - 31 Jul
The Bungalow, Pool, Dock, Kayaks, & Game Room
Coffee/tea maker, fridge, microwave, oven

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, (13 reviews)
"Host was very accommodating and accessible, had a great time as a family"
United States
Elizabeth D.
The price is HK$7,370
HK$10,611 total
includes taxes & fees
18 Aug - 19 Aug
8 Miles to Busch Gardens/Spacious Family Getaway/ 7Bedroom/3 masters /5 Bath
Coffee/tea maker, fridge, microwave, oven

-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!

-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!
Newport News
9.6 out of 10, Exceptional, (12 reviews)
"Everything was very clean good coffee options plenty of hot water :)"
United States
Allen C.
The price is HK$3,129
HK$4,760 total
includes taxes & fees
2 Aug - 3 Aug
-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!
Microwave, oven, stovetop, dishwasher

Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~

Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
Kilmarnock
10.0 out of 10, Exceptional, (3 reviews)
"Nice rambler in a great in town location with hot tub, firepit, and fenced in yard. Also great value for the price. "
United States
Melinda H.
The price is HK$1,411
HK$3,314 total
includes taxes & fees
17 Aug - 18 Aug
Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
Desk, iron/ironing board, free WiFi

Belle Haven - High Speed internet, walk to town

Belle Haven - High Speed internet, walk to town
Kilmarnock
10.0 out of 10, Exceptional, (38 reviews)
"Great cottage, beautiful place to stay at"
United States
Darren W.
The price is HK$1,137
HK$2,504 total
includes taxes & fees
27 Jul - 28 Jul
Belle Haven - High Speed internet, walk to town
Interior

Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.6 out of 10, Exceptional, (30 reviews)
"We loved our stay here! The property is gorgeous, the rooms are bright and spacious, and the kitchen had everything we needed for a week long stay. The kids really loved being able to spend time in the back yard looking at the water and watching the jets fly overhead. Would definitely recommend and will rebook whenever we’re back in town! "
United States
Clare G.
The price is HK$1,744
HK$4,568 total
includes taxes & fees
12 Aug - 13 Aug
Sojourn Aviators Dream on Back River
Smart TV, fireplace, books, stereo

Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great value for the money, great hosts, very renter friendly"
United States
WILLIAM M.
The price is HK$1,059
HK$3,929 total
includes taxes & fees
28 Jul - 29 Jul
Unique Luxurious Waterfront in Hampton
Exterior detail

The Nook in Kilmarnock Va 3 bedroom

The Nook in Kilmarnock Va 3 bedroom
Kilmarnock
10.0 out of 10, Exceptional, (4 reviews)
"This home is comfortable, well appointed, and in a great location. Host is accommodating and communicates appropriately I highly recommend this property!"
United States
Anonymous traveller
The price is HK$1,137
HK$3,491 total
includes taxes & fees
27 Jul - 28 Jul
The Nook in Kilmarnock Va 3 bedroom
Beach towels

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, (56 reviews)
"House was layed out perfectly for our family of 11. The yard could have used some TLC. Overall very good stay."
United States
John S.
The price is HK$5,316
HK$7,762 total
includes taxes & fees
27 Jul - 28 Jul
Family friendly 5 bedroom home within Walking distance To CNU
Exterior

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, (7 reviews)
"First and foremost, the property was excellent! The host, Michael was extremely welcoming and kind. The property is in top condition with new everything! The seclusion and lakefront location was to die for. Highly recommend this property as we will be back! "
United States
Kelly B.
The price is HK$2,823
HK$5,614 total
includes taxes & fees
4 Aug - 5 Aug
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Dining

5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis

5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis
Hampton
9.8 out of 10, Exceptional, (42 reviews)
"Everyone loved the place!"
United States
Gail R.
The price is HK$4,407
HK$6,597 total
includes taxes & fees
24 Aug - 25 Aug
5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis
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

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

10/10 Excellent
"Nice"
Dean 1-night trip
Posted 2 hours ago
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Find out more about Gloucester

Gloucester Vacation Homes information

Number of reviews
301
Accommodation
352 Vacation Homes
Lowest Price
HK$1,948
Highest Price
HK$10,611

Explore a world of travel with Expedia