Holiday Houses in Gloucester

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207 Holiday homes

Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

from £203 / night

£1,306 - £3,054 / week

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

6

from £147 / night

£916 - £1,695 / week

Golden Sands at Good Harbor: Across the street from the beach

Gloucester cottage

7 bedrooms / 3 bathrooms / sleeps 12

from £587 / night

£4,064 - £4,904 / week

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 10

2

from £524 / night

£3,664 / week

Inviting apartment with harbor views, fireplace, patio, & gas grill!

Gloucester house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 43 minutes

from £163 / night

£1,142 / week

Vintage Home directly on the Annisquam River

Gloucester house

6 bedrooms / 3 bathrooms / sleeps 12

2

from £288 / night

£2,015 / week

Waterfront Woodsy 3BR Cottage

Gloucester house

3 bedrooms / 1 bathroom / sleeps 6

1

from £321 / night

£2,244 / week

Lovely 'Blue Heron Cottage' on Annisquam River!

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 6

1

Responds fast! avg. 42 minutes

from £185 / night

£1,294 / week

Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 5

10

from £110 / night

£770 - £1,567 / week

Fabulous Waterfront 2 Bedroom - Boat dock option

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

from £161 / night

£1,122 / week

Water's Edge: Direct waterfront on picturesque Goose Cove with dock

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

from £281 / night

£1,848 - £2,832 / week

Seaside House: Good Harbor Beach and the Back Shore right outside

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

from £520 / night

£3,633 - £6,856 / week

Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach

Gloucester house

5 bedrooms / 3 bathrooms / sleeps 9

from £588 / night

£4,057 - £8,194 / week

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

3

Responds fast! avg. 2 hours 16 minutes

from £106 / night

£738 / week

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 7

from £260 / night

£1,667 - £4,017 / week

Waterfront Vacation House w/ Dock

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 10 minutes

from £275 / night

£2,061 / week

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

from £472 / night

£2,999 - £8,207 / week

Salt Island Views: Walking distance to Good Harbor & Long Beach.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

from £380 / night

£2,645 - £5,332 / week

Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

from £156 / night

£1,089 - £1,969 / week

Cool Cove: Wingaersheek Beach plus your own private beach & all those views!

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 8

1

from £683 / night

£4,628 - £6,442 / week

Wonson Cove House: Rocky Neck, Eastern Point and Beaches

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

from £346 / night

£2,392 - £6,056 / week

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / sleeps 2

from £152 / night

£893 / week

Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 43 minutes

from £118 / night

£821 / week

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 7

from £406 / night

£2,679 - £3,784 / week

Strawberry Cove House: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 10

from £576 / night

£3,696 - £5,184 / week

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 6

from £303 / night

£2,071 - £2,981 / week

Sea Fox: Custom-designed home with rights to private Coffins Beach

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 8

from £394 / night

£2,714 - £5,250 / week

Close to Half Moon Bay

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

1

from £115 / night

£683 / week

Eastern Point on the Sea: Water views, private beach and gorgeous sunrises

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 7

from £532 / night

£3,517 - £5,212 / week

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 21 minutes

from £101 / night

£706 / week

Quiet cottage near beach

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

from £156 / night

£1,090 / week

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches

Gloucester house

2 bedrooms / 1 bathroom / sleeps 6

from £169 / night

£1,099 - £1,656 / week

Little Red House: Close to Gloucester's historic Stage Fort Park & beaches

Gloucester house

3 bedrooms / 1 bathroom / sleeps 5

1

from £172 / night

£1,107 - £1,527 / week

Long Beach House: Large, comfortable home just 285 feet from the white sands!

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

from £318 / night

£2,216 - £3,014 / week

Family Tides: Only a half-mile from Good Harbor Beach.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

from £311 / night

£2,047 - £4,195 / week

Nature Lover's Paradise .5-1mile to beaches, nature walks, golf, museums, couple

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 36 minutes

from £102 / night

£661 - £1,629 / week

Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

from £376 / night

£2,498 - £5,592 / week

Reeds Wharf is a charming one bedroom condo, overlooking Smith Cove.

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 4

from £145 / night

£1,011 / week

Rockwood Cottage

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

from £344 / night

£2,404 / week

High Rock Cottage: Astounding views from every angle!

Gloucester house

6 bedrooms / 4 bathrooms / sleeps 10

from £862 / night

£6,029 - £9,364 / week

Viewing 40 of 207
rentals in Gloucester

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