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
Stay at this holiday home in Hampton. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Hampton Beach and Ocean Gaming Casino are located ...
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 NZ$983 per night from 11 June to 12 June
NZ$983
11 June - 12 June
includes taxes & fees
Stay at this holiday home in Gloucester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Wingaersheek Beach and Plum Cove Beach are located ...
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
Stay at this holiday home in Newbury. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Newbury Beach and Plum Island Point are located ...
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
Stay at this beach holiday home in Hampton. Enjoy a beach locale, a garden and laundry facilities. Popular attractions Hampton Beach and 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
Stay at this holiday home in Marblehead. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Riverhead Beach 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
Stay at this family-friendly holiday home in Rockport. Enjoy a garden, laundry facilities and patios. Popular attractions Wingaersheek 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
Stay at this golf holiday home in Salem. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Witch Dungeon Museum and Witch House are located ...
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
Stay at this holiday home in Marblehead. Enjoy a garden, laundry facilities and patios. Popular attractions Mud Puddle Toys and Gas House Beach are located ...
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
Stay at this holiday home in Hampton. Enjoy a garden, laundry facilities and patios. Popular attractions Hampton Beach and Hampton Beach Casino are located ...
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
535 Holiday Homes
Lowest Price
NZ$334
Highest Price
NZ$983
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

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue Gloucester MA
The price is NZ$343 per night from 18 May to 19 May
NZ$343
18 May - 19 May
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowCastle Manor Inn
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
The price is NZ$505 per night from 31 May to 1 June
NZ$505
31 May - 1 June
includes taxes & fees
Stay at this beach hotel in Gloucester. Enjoy free Wi-Fi, a beach locale and a rooftop terrace. Our guests praise the helpful staff and the property condition ...
Opens in a new windowBeauport Hotel Gloucester
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 NZ$334 per night from 18 May to 19 May
NZ$334
18 May - 19 May
includes taxes & fees
Stay at this golf hotel in Gloucester. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
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 NZ$430 per night from 18 May to 19 May
NZ$430
18 May - 19 May
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free parking, a marina and a 24-hour front desk. Our guests praise the breakfast and the restaurant in their reviews. ...
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.