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Holiday Houses in Gloucester

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157 Holiday homes

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

from £418 / night

£2,317 / week

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

Gloucester cottage

7 bedrooms / 3 bathrooms / sleeps 12

from £1,154 / night

£6,767 / week

Lovely 'Blue Heron Cottage' on Annisquam River!

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 6

1

Responds fast! avg. 44 minutes

from £138 / night

£961 / week

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 10

2

from £538 / night

£3,765 / week

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

3

from £101 / night

£704 / week

Vintage Home directly on the Annisquam River

Gloucester house

6 bedrooms / 3 bathrooms / sleeps 12

2

from £295 / night

£2,067 / week

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

from £674 / night

£4,192 / week

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / sleeps 2

from £145 / night

£856 / week

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

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

from £662 / night

£4,532 / 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 £980 / night

£5,814 / week

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

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

from £259 / night

£1,811 / week

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

from £924 / night

£5,403 / week

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

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 7

from £408 / night

£2,252 / week

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 7

from £701 / night

£4,113 / week

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

Gloucester house

2 bedrooms / 1 bathroom / sleeps 6

from £334 / night

£1,829 / week

Magnolia Tides: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 10

from £1,226 / night

£7,420 / week

Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

from £99 / night

£691 - £1,461 / week

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 6

from £524 / night

£3,009 / week

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

from £150 / night

£1,050 / week

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

from £87 / night

£674 / week

Bell View: Private tennis court and an in-law suite.

Gloucester house

6 bedrooms / 5 bathrooms / sleeps 16

from £1,046 / night

£7,320 / week

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

from £558 / night

£3,826 / week

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

from £638 / night

£3,653 / week

Two Beaches: Walk to Long Beach or Good Harbor!

Gloucester house

3 bedrooms / 1 bathroom / sleeps 8

from £428 / night

£2,922 / week

Rockwood Cottage

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

from £329 / night

£2,299 / week

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

2 bedrooms / 1 bathroom / sleeps 6

17

from £230 / night

£1,610 - £1,919 / week

Relax at Rocky Neck Hideaway

Gloucester townhouse

1 bedroom / 1 bathroom / sleeps 3

from £118 / night

£826 / week

Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 8

from £377 / night

£3,012 / week

Charming cottage near the ocean w/beach access & near Gloucester!

Gloucester cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 22 minutes

from £141 / night

£985 / week

Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

from £312 / night

£1,720 / week

Beach Walk: Good Harbor Beach footbridge just steps away!

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

from £233 / night

£1,583 / week

Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

from £524 / night

£2,962 / week

Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 10

from £770 / night

£4,494 / week

Kris' Kottage at Long Beach

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 6

from £445 / night

£2,508 / week

Plaisance - a summer vacation rental near Bass Rocks

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

from £552 / night

£3,124 / week

Helena House: European flair, close to Plum Cove Beach.

Gloucester house

3 bedrooms / 1 bathroom / sleeps 7

from £258 / night

£1,636 / week

Cedar Ledge Annisquam: Ocean views & traditional New England charm.

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 14

from £931 / night

£5,317 / week

Waterfront Wonder

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 56 minutes

from £454 / night

£3,175 - £3,810 / week

Test Property- TA Test

Gloucester cottage

1 bedroom / 1 bathroom / sleeps 2

from £12 / night

£15 / week

Rocky Neck Hilltop: Living is easy high atop Rocky Neck!

Gloucester condo

2 bedrooms / 2 bathrooms / sleeps 4

from £318 / night

£1,733 / week

Viewing 40 of 157
rentals in Gloucester