Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

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
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
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Gloucester,
When you stay at this vacation home in Gloucester, you'll be on the waterfront, within a 15-minute drive of Good Harbor Beach and Cape Ann.
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
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!
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Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Marblehead
With a stay at this vacation home, you'll be centrally located in Marblehead, within a 10-minute drive of Salem Witch Museum and Marblehead Museum & Historical ...
Best location in Old Town home, 5 minutes to everything, enjoy the difference!
Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester
With a stay at this vacation home in Gloucester, you'll be by the sea, within a 15-minute drive of Cape Ann and Plum Cove Beach.
Beach Life Bliss - steps to the beach
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.
Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

Hampton
When you stay at this vacation home in Hampton, you'll be by the sea, a 1-minute drive from Hampton Beach and 7 minutes from Seabrook Beach.
Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach
Island SunRise: Sunsets too!  360 WaterViews! Waterfront, Grill, Firepit, Central AC

Island SunRise: Sunsets too! 360 WaterViews! Waterfront, Grill, Firepit, Central AC

Newbury
Located in Newbury, this vacation home is on the waterfront, a 4-minute walk from Plum Island Beach and within a 5-minute drive of Newbury Beach.
Island SunRise: Sunsets too! 360 WaterViews! Waterfront, Grill, Firepit, Central AC
House near down town Salem

House near down town Salem

Salem
With a stay at this vacation home in Salem, you'll be within a 5-minute drive of Salem Witch Museum and Witch House.
House near down town 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
Highest Price
Popular accommodation
Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean, "Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Best location in Old Town home, 5 minutes to everything, enjoy the difference!, Beach Life Bliss - steps to the beach, Walk to Beach. Private Nature and Bird Watching Trail. Quiet., Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach, Island SunRise: Sunsets too! 360 WaterViews! Waterfront, Grill, Firepit, Central AC, House near down town Salem

Top trending hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
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
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
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
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
When you stay at The Vista in Gloucester, you'll be by the ocean, a 1-minute drive from Good Harbor Beach and 6 minutes from Cape Ann.
The Vista
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Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
Located in Gloucester, Atlantis Oceanfront Inn is by the ocean, within a 10-minute drive of Cape Ann and Motif No 1.
Atlantis Oceanfront Inn
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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.