Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

 Steps away to the beach - Surf - Sun & Sand beach house

Steps away to the beach - Surf - Sun & Sand beach house

Hampton NH
With a stay at this vacation home in Hampton (Hampton Beach), you'll be steps from Hampton Beach and 4 minutes by foot from Ocean Gaming Casino.
Opens in a new window Steps away to the beach - Surf - Sun & Sand beach house
Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester MA
The price is AU$683 per night from 22 May to 23 May
AU$683
22 May - 23 May
includes taxes & fees
Located in Gloucester, this vacation home is by the sea, a short 3-minute walk from Plum Cove Beach and within 4 minutes by car from Halibut Point State ...
Opens in a new windowBeach 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 MA
Located in Newbury, this vacation home is by the sea, within a 5-minute walk of Plum Island Beach and Newbury Beach.
Opens in a new windowWalk to Beach. Private Nature and Bird Watching Trail. Quiet.
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Beach House, Walking distance to downtown!

Beach House, Walking distance to downtown!

Hampton NH
With a stay at this vacation home, you'll be centrally located in Hampton, steps from Hampton Beach and 8 minutes by foot from Hampton Beach Casino.
Opens in a new windowBeach House, Walking distance to downtown!
Charming private townhouse-style lodging, a block from Marblehead Harbor

Charming private townhouse-style lodging, a block from Marblehead Harbor

Marblehead MA
A stay at this vacation home places you in the heart of Marblehead, within a 15-minute walk of King Hooper Mansion and Marblehead Museum & Historical ...
Opens in a new windowCharming private townhouse-style lodging, a block from Marblehead Harbor
Home with washer/dryer, gas grill, & outdoor dining - walk 5 minutes to beach

Home with washer/dryer, gas grill, & outdoor dining - walk 5 minutes to beach

Rockport MA
When you stay at this vacation home in Rockport, you'll be by the sea, within a 10-minute walk of Back Beach and Front Beach.
Opens in a new windowHome with washer/dryer, gas grill, & outdoor dining - walk 5 minutes to beach
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Salem MA
A stay at this vacation home places you in the heart of Salem, within a 15-minute walk of Witch House and Witch Dungeon Museum.
Opens in a new windowLeslie's Retreat: Spacious home ideally located to everything
2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach

Marblehead MA
The price is AU$558 per night from 3 June to 4 June
AU$558
3 June - 4 June
includes taxes & fees
A stay at this vacation home places you in the heart of Marblehead, within a 10-minute walk of Gas House Beach and Mud Puddle Toys.
Opens in a new window2BR Historic Marblehead Home+Minutes to Beach
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 NH
When you stay at this vacation home in Hampton, you'll be by the sea, and a 3-minute walk from Hampton Beach and 5 minutes by foot from North Beach.
Opens in a new windowCoastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach
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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
538 Holiday Homes
Lowest Price
AU$269
Highest Price
AU$683
Popular accommodation
Steps away to the beach - Surf - Sun & Sand beach house, Beach Life Bliss - steps to the beach, Walk to Beach. Private Nature and Bird Watching Trail. Quiet., Beach House, Walking distance to downtown!, Charming private townhouse-style lodging, a block from Marblehead Harbor, Home with washer/dryer, gas grill, & outdoor dining - walk 5 minutes to beach, Leslie's Retreat: Spacious home ideally located to everything, 2BR Historic Marblehead Home+Minutes to Beach, Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

Top trending hotels in Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
The price is AU$406 per night from 17 May to 18 May
AU$406
17 May - 18 May
includes taxes & fees
With a stay at Beauport Hotel Gloucester in Gloucester (Downtown Gloucester), you'll be steps from Pavilion Beach and 3 minutes by foot from Massachusetts ...
Opens in a new windowBeauport Hotel Gloucester
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue Gloucester MA
The price is AU$276 per night from 17 May to 18 May
AU$276
17 May - 18 May
includes taxes & fees
Located in Gloucester, Castle Manor Inn is by the ocean, within a 5-minute drive of Stage Fort Park and Fishermen's Memorial Monument.
Opens in a new windowCastle Manor Inn
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd Gloucester MA
Fully refundableReserve now, pay when you stay
The price is AU$269 per night from 17 May to 18 May
AU$269
17 May - 18 May
includes taxes & fees
With a stay at Ocean House Hotel at Bass Rocks in Gloucester (East Gloucester), you'll be within a 5-minute drive of Good Harbor Beach and Maritime ...
Opens in a new windowOcean House Hotel at Bass Rocks
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The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue Gloucester MA
Fully refundableReserve now, pay when you stay
The price is AU$346 per night from 17 May to 18 May
AU$346
17 May - 18 May
includes taxes & fees
Located in Gloucester, The Hotel at Cape Ann Marina is a 4-minute drive from Hammond Castle and 10 minutes from Wingaersheek Beach.
Opens in a new windowThe Hotel at Cape Ann Marina
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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.