Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus

*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus

Salem MA
A stay at this vacation home places you in the heart of Salem, within a 15-minute walk of Salem Common and Salem Witch Museum.
Opens in a new window*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus
2 Bed/2 Bath Private Beach House One Block from the ocean.

2 Bed/2 Bath Private Beach House One Block from the ocean.

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 window2 Bed/2 Bath Private Beach House One Block from the ocean.
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester MA
With a stay at this vacation home, you'll be centrally located in Gloucester, just a 5-minute walk from Stage Fort Park and 10 minutes by foot from Fishermen's ...
Opens in a new window3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
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3BR Salem Townhouse Minutes to downtown

3BR Salem Townhouse Minutes to downtown

Salem MA
With a stay at this vacation home in Salem, you'll be within a 15-minute walk of Glendale Cove Beach and Salem Pioneer Village 1630.
Opens in a new window3BR Salem Townhouse Minutes to downtown
Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport

Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport

Newburyport MA
A stay at this vacation home places you in the heart of Newburyport, steps from Historical Society of Old Newbury and 5 minutes by foot from Sisters We ...
Opens in a new windowBeautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport
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 NH
The price is AU$857 per night from 31 Mar to 1 Apr
AU$857
31 Mar - 1 Apr
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.
Opens in a new windowPremier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Rockport MA
With a stay at this vacation home in Rockport, you'll be on the beach, just a 3-minute walk from Long Beach and 11 minutes by foot from Cape Hedge Beach.
Opens in a new windowOceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
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 MA
A stay at this vacation home places you in the heart of Salem, steps from Salem Witch Trials Memorial and New England Pirate Museum.
Opens in a new windowPrime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Stunning Beach Cottage just steps from Marblehead Harbor and Town

Stunning Beach Cottage just steps from Marblehead Harbor and Town

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 windowStunning Beach Cottage just steps from Marblehead Harbor and Town
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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
539 Holiday Homes
Lowest Price
AU$291
Highest Price
AU$857
Popular accommodation
*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus, 2 Bed/2 Bath Private Beach House One Block from the ocean., 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8, 3BR Salem Townhouse Minutes to downtown, Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport, Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!, Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Stunning Beach Cottage just steps from Marblehead Harbor and Town

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$364 per night from 31 Mar to 1 Apr
AU$364
31 Mar - 1 Apr
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$291 per night from 18 Apr to 19 Apr
AU$291
18 Apr - 19 Apr
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
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$349 per night from 31 Mar to 1 Apr
AU$349
31 Mar - 1 Apr
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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Long Beach Suites

Long Beach Suites

2 out of 5
28 Rockport Rd Gloucester MA
Located in Gloucester (East Gloucester), this aparthotel is within a 5-minute drive of Cape Hedge Beach and Long Beach.
Opens in a new windowLong Beach Suites
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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.