Book Holiday Homes in Gloucester

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Gloucester

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

Gloucester
Stay at this vacation home in Gloucester. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Good Harbor Beach and Wingaersheek Beach ...
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.

Walk to Beach. Private Nature and Bird Watching Trail. Quiet.

Newbury
Stay at this vacation home in Newbury. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Seabrook Beach and Newbury Beach are located ...
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Salem
The price is NZ$753 per night from 4 Aug to 5 Aug
NZ$753
4 Aug - 5 Aug
includes taxes & fees
Stay at this vacation home in Salem. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Salem Witch Museum and Salem Custom House are located ...
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Save an average of 15% on thousands of hotels when you're signed in
Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

marblehead
The price is NZ$1,403 per night from 11 Aug to 12 Aug
NZ$1,403
11 Aug - 12 Aug
includes taxes & fees
Stay at this vacation home in Marblehead. Enjoy a fitness center, laundry facilities, and patios. Popular attractions Salem Witch Museum and Salem Harbor are ...
Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean
Centrally located charmer with expansive patio, board games, & central AC

Centrally located charmer with expansive patio, board games, & central AC

Gloucester
Stay at this vacation home in Gloucester. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Good Harbor Beach and Wingaersheek ...
Centrally located charmer with expansive patio, board games, & central AC
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Hampton
The price is NZ$1,188 per night from 19 Aug to 20 Aug
NZ$1,188
19 Aug - 20 Aug
includes taxes & fees
Book a stay at this beach vacation home in Hampton. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Hampton Beach and Ocean Gaming Casino ...
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Salem
Book a stay at this golf vacation home in Salem. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Salem Witch Museum and Witch Dungeon ...
Leslie's Retreat: Spacious home ideally located to everything
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Salem
The price is NZ$578 per night from 3 Aug to 4 Aug
NZ$578
3 Aug - 4 Aug
includes taxes & fees
Stay at this vacation home in Salem. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Salem Witch Museum and New England ...
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Charming 3-bedroom house in the HEART of  SALEM!

Charming 3-bedroom house in the HEART of SALEM!

Salem
Stay at this property in Salem. Enjoy laundry facilities and air conditioning. Popular attractions Salem Witch Museum and House of the Seven Gables are located ...
Charming 3-bedroom house in the HEART of SALEM!
Don't see what you're looking for?
See all available properties in Gloucester
View all properties
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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Gloucester vacation homes are the perfect way for you to wing it.

Holiday houses in Gloucester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Gloucester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Gloucester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Gloucester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Gloucester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Gloucester Holiday Homes essential information

Accommodation
575 Holiday Homes
Lowest Price
NZ$304
Highest Price
NZ$1,403
Popular accommodation
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester, Walk to Beach. Private Nature and Bird Watching Trail. Quiet., Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC , Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean, Centrally located charmer with expansive patio, board games, & central AC, Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!, Leslie's Retreat: Spacious home ideally located to everything, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Charming 3-bedroom house in the HEART of SALEM!

Top trending hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is NZ$304 per night from 14 Aug to 15 Aug
NZ$304
14 Aug - 15 Aug
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
Stay at this 3.5-star beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property ...
Beauport Hotel Gloucester
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
The price is NZ$453 per night from 2 Sept to 3 Sept
NZ$453
2 Sept - 3 Sept
includes taxes & fees
Stay at this 3-star beach motel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Atlantis Oceanfront Inn
Save an average of 15% on thousands of hotels when you're signed in
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
The price is NZ$564 per night from 2 Sept to 3 Sept
NZ$564
2 Sept - 3 Sept
includes taxes & fees
Stay at this 4-star golf hotel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Ocean House Hotel at Bass Rocks
Don't see what you're looking for?
See all available properties in Gloucester
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.