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Holiday Lettings
> North America
> United States
> Massachusetts
> Cape Ann
> Houses and Apartments in Gloucester

Houses in Gloucester and Apartments – Holiday Lettings - Holiday Rentals Gloucester

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£1 £750 -

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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185 Holiday homes

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Holiday cottage accommodation

Gloucester cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £11 / night

£14 / week

1 / 4

Holiday apartment in Gloucester

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3
3 reviews

from £206 / night

£1,440 / week

1 / 26

Gloucester holiday home rental

Gloucester house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 10
2 reviews

from £523 / night

£3,657 / week

1 / 18

Holiday home in Gloucester

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £262 / night

£1,829 / week

1 / 13

Cottage rental in Gloucester

Gloucester cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Beautifully Decorated and Conveniently Located” Summerwind Cottage is beautifully decorated, inside and out, and conveniently located within walking distance of the beach, a very cool artist colony, fish and lobster markets, and the downtown Gloucester area. The well equipped kitchen and outdoor grill made cooking at the cottage enjoyable and relaxing. Sunsets from the deck are spectacular. Our hosts, Linda and Frank, provided great insider tips on where to go and what to see. We were looking for a quiet relaxing week, and we were not dissapointed with Summerwind Cottage.

17 reviews

from £275 / night

£1,920 / week

1 / 28

Holiday home in Gloucester

Gloucester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £823 / night

£5,760 / week

1 / 34

Holiday apartment in Gloucester

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2
1 review

from £127 / night

£878 / week

1 / 13

Gloucester holiday home rental

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6
1 review

from £320 / night

£2,240 / week

1 / 68

Holiday cottage in Gloucester

Gloucester cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £380 / night

£2,655 / week

1 / 30

Holiday home in Gloucester

Gloucester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £260 / night

£1,817 / week

1 / 29

Holiday apartment letting

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £143 / night

£1,001 / week

1 / 23

Gloucester holiday home rental

Gloucester house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £240 / night

£1,677 / week

1 / 22

Gloucester holiday home rental

Gloucester house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £430 / night

£3,007 / week

1 / 24

Holiday home in Gloucester

Gloucester house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £212 / night

£1,482 / week

1 / 19

Apartment rental in Gloucester

Gloucester apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £214 / night

£1,493 / week

1 / 20

Home rental in Gloucester

Gloucester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

from £435 / night

£3,041 / week

1 / 23

Holiday cottage in Gloucester

Gloucester cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £230 / night

£1,610 / week

1 / 30

Holiday home in Gloucester

Gloucester house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £511 / night

£3,572 / week

1 / 30

Home rental in Gloucester

Gloucester house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £479 / night

£3,354 / week

1 / 21

Gloucester ski home to rent.

Gloucester house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 15

from £619 / night

£4,332 / week

1 / 24

Gloucester ski studio to rent.

Gloucester studio

  • Studio
  • 2 bathrooms
  • sleeps 4

from £223 / night

£1,560 / week

1 / 22

Gloucester holiday apartment rental

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £127 / night

£889 / week

1 / 30

Holiday cottage in Gloucester

Gloucester cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £120 / night

£839 / week

1 / 21

Holiday home in Gloucester

Gloucester house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £230 / night

£1,605 / week

1 / 30

Holiday apartment in Gloucester

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £104 / night

£727 / week

1 / 12

Gloucester holiday home rental

Gloucester house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £308 / night

£2,152 / week

1 / 30

Gloucester holiday apartment rental

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £160 / night

£1,118 / week

1 / 13

Home rental in Gloucester

Gloucester house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £270 / night

£1,890 / week

1 / 28

Holiday home in Gloucester

Gloucester house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £491 / night

£3,432 / week

1 / 16

Holiday home in Gloucester

Gloucester house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £131 / night

£911 / week

1 / 23

Gloucester holiday home rental

Gloucester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from £265 / night

£1,850 / week

1 / 30

Condo rental in Gloucester

Gloucester condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £365 / night

£2,555 / week

1 / 30

Holiday home in Gloucester

Gloucester house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £216 / night

£1,510 / week

1 / 27

Holiday home in Gloucester

Gloucester house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

from £445 / night

£3,114 / week

1 / 24

Gloucester holiday home rental

Gloucester house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

from £567 / night

£3,963 / week

1 / 18

Holiday home in Gloucester

Gloucester house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £252 / night

£1,761 / week

1 / 23

Holiday apartment rental

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £120 / night

£839 / week

1 / 10

Ski home to rent in Gloucester

Gloucester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £671 / night

£4,695 / week

1 / 24

Holiday apartment in Gloucester

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £87 / night

£604 / week

1 / 12

Holiday apartment in Gloucester

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £140 / night

£979 / week

1 / 12

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Gloucester holidays

Located on the northern shores of Massachusetts, the town of Gloucester is a holiday paradise that generations of travellers return to every year. The winding streets of this historic town are lined with quaint shops, interesting museums, charming cafes, and unforgettable seafood restaurants. Come here to experience the beautiful rocky coastlines and soft sand beaches of Massachusetts. Hike the trails and stop at breathtaking overlooks with views of the Atlantic Ocean. Visit historic homes and lighthouses. Spend the afternoon swimming, snorkelling, or relaxing on a pristine beach. And then go home at night to your own private holiday rental and host dinner for your family and friends. Many holiday rentals in Gloucester are less expensive than hotels and offer more space and better amenities. Wake up in the morning and watch the sun rise from the deck of your beach condo or summer house, then head downtown to spend the day exploring and making fun holiday memories.

Here are a few additional suggestions for your trip:

  • Take a brewery tour: Gloucester is the traditional home of several long established breweries and craft distilleries. Taste some of the area's award winning artisanal spirits.
  • Tour Hammond Castle: This extraordinary structure was once the home of John Hays Jr., a wealthy eccentric who amassed an extensive collection of medieval artefacts.
  • Visit the Fisherman's Memorial Monument: This fascinating memorial was built in 1925 to honour all the fishermen who have been lost at sea since the 17th century.
  • Play on the beach: Swim, build a sandcastle, or just relax on Good Harbor Beach or Stage Fort Park and Beach, two of the most popular beach destinations in the area.
  • Visit the Rocky Neck Art Colony: This is the oldest established colony for artists in the United States and has been a destination for art lovers since the 1840s.
  • Visit the Beauport Museum or the Cape Ann Historical Museum: Learn more about the fascinating history of Cape Ann with the changing exhibits of these popular museums.

Gloucester offers an ideal scenic back drop for whatever holiday activities you have in mind. The best way to enjoy it all is with a stay in your own apartment rental or summer condo. Find a luxury holiday rental just a few steps from the beach that offers all the amenities you and your family need. While you're visiting Gloucester, be sure to plan day trips to coastal destinations nearby like Cape Cod and Plymouth.

Also consider