Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Hampton Beach Cottage - River/Beach 2 Block Walk

Hampton Beach Cottage - River/Beach 2 Block Walk

Hampton
With a stay at this vacation home in Hampton (Hampton Beach), you'll be within a 10-minute walk of Hampton Beach and Ocean Gaming Casino.
Hampton Beach Cottage - River/Beach 2 Block Walk
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 AU$440 per night from 6 May to 7 May
AU$440
includes taxes & fees
6 May - 7 May
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!
Entire Home 2BR 2BTH Quite Area with parking

Entire Home 2BR 2BTH Quite Area with parking

Lynn
Located in Lynn, this vacation home is within a 15-minute drive of Encore Boston Harbor and TD Garden.
Entire Home 2BR 2BTH Quite Area with parking
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Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck

Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck

Rockport
With a stay at this vacation home, you'll be centrally located in Rockport, a 4-minute drive from Cape Ann and 6 minutes from Good Harbor Beach.
Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

Newburyport
The price is AU$738 per night from 13 May to 14 May
AU$738
includes taxes & fees
13 May - 14 May
Located in Newburyport, this vacation home is by the sea, a 5-minute drive from Newbury Beach and 6 minutes from Plum Island Beach.
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi
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
Massachusetts Abode w/ Deck & Grill: Near Beaches!

Massachusetts Abode w/ Deck & Grill: Near Beaches!

Gloucester
With a stay at this vacation home in Gloucester, you'll be a 1-minute drive from Good Harbor Beach and 7 minutes from Cape Ann.
Massachusetts Abode w/ Deck & Grill: Near Beaches!
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Gloucester
With a stay at this vacation home, you'll be centrally located in Gloucester, a 2-minute drive from Good Harbor Beach and 8 minutes from Cape Ann.
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

2 out of 5
Marblehead
The price is AU$927 per night from 6 May to 7 May
AU$927
includes taxes & fees
6 May - 7 May
With a stay at this vacation home in Marblehead, you'll be within a 15-minute drive of Salem Witch Museum and Massachusetts Bay.
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
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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
555 Holiday Homes
Lowest Price
AU$296
Highest Price
AU$927
Popular accommodation
Hampton Beach Cottage - River/Beach 2 Block Walk, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Entire Home 2BR 2BTH Quite Area with parking, Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck, Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi, Leslie's Retreat: Spacious home ideally located to everything, Massachusetts Abode w/ Deck & Grill: Near Beaches!, Classic charmer near the coast with with a firepit, outdoor shower, & beach gear, The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

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$408 per night from 4 May to 5 May
AU$408
includes taxes & fees
4 May - 5 May
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
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is AU$347 per night from 7 May to 8 May
AU$347
includes taxes & fees
7 May - 8 May
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
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is AU$305 per night from 4 May to 5 May
AU$305
includes taxes & fees
4 May - 5 May
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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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$296 per night from 12 May to 13 May
AU$296
includes taxes & fees
12 May - 13 May
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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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.