Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

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

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

Gloucester
Located in Gloucester, this vacation home is within a 15-minute drive of Good Harbor Beach and Cape Ann.
"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
Located in Newbury, this vacation home is by the sea, within a 5-minute walk of Plum Island Beach and Newbury Beach.
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
When you stay at this vacation home in Salem, you'll be by the sea, within a 10-minute walk of Salem Witch Museum and Salem Custom House.
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
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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 AU$1,293 per night from 11 Aug to 12 Aug
AU$1,293
11 Aug - 12 Aug
includes taxes & fees
With a stay at this vacation home in Marblehead, you'll be by the sea, within a 10-minute drive of Salem Witch Museum and Marblehead Museum & Historical ...
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
With a stay at this vacation home, you'll be centrally located in Gloucester, within a 10-minute drive of Good Harbor Beach and Cape Ann.
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 AU$1,097 per night from 19 Aug to 20 Aug
AU$1,097
19 Aug - 20 Aug
includes taxes & fees
A stay at this vacation home places you in the heart of Hampton, within a 10-minute walk of 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
With a stay at this vacation home, you'll be centrally located in Salem, within a 5-minute drive of Salem Witch Museum and Witch House.
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
This vacation home is in the heart of Salem, within a 5-minute walk of Salem Witch Trials Memorial and Salem Witch Museum.
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
A stay at this property places you in the heart of Salem, within a 10-minute walk of Salem Witch Museum and House of the Seven Gables.
Charming 3-bedroom house in the HEART of SALEM!
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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.

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
AU$278
Highest Price
AU$1,293
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 AU$278 per night from 18 Aug to 19 Aug
AU$278
18 Aug - 19 Aug
includes taxes & fees
When you stay at Castle Manor Inn in Gloucester, you'll be by the ocean, within a 15-minute drive of Wingaersheek Beach and Good Harbor Beach.
Castle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is AU$820 per night from 3 Sept to 4 Sept
AU$820
3 Sept - 4 Sept
includes taxes & fees
When you stay at Beauport Hotel Gloucester in Gloucester, you'll be on the beach, within a 10-minute drive of Good Harbor Beach and Cape Ann.
Beauport Hotel Gloucester
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
The price is AU$530 per night from 4 Sept to 5 Sept
AU$530
4 Sept - 5 Sept
includes taxes & fees
Located in Gloucester, Ocean House Hotel at Bass Rocks is by the ocean, within a 5-minute drive of Good Harbor Beach and Maritime Gloucester.
Ocean House Hotel at Bass Rocks
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Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
The price is AU$299 per night from 4 Sept to 5 Sept
AU$299
4 Sept - 5 Sept
includes taxes & fees
When you stay at Sea Lion Motel and Cottages in Gloucester, you'll be near the beach, a 2-minute drive from Good Harbor Beach and 7 minutes from Cape Ann.
Sea Lion Motel and Cottages
Don't see what you're looking for?
See all available properties in Gloucester
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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.

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^Subject to availability and chosen travel dates.