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Gloucester Holiday Rentals

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66 rentals in Gloucester.
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Good Harbor Beach House, holiday rental in Gloucester

Good Harbor Beach House

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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On the Cove - Beautiful Apartment Right on Lanes Cove, holiday rental in Gloucester

On the Cove - Beautiful Apartment Right on Lanes Cove

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Willow House - Garden Setting, Ocean View, Steps to Rocky Neck!, holiday rental in Gloucester

Willow House - Garden Setting, Ocean View, Steps to Rocky Neck!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Quality Accommodations in Quiet Seaside Village, holiday rental in Gloucester

Quality Accommodations in Quiet Seaside Village

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak, holiday rental in Gloucester

BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated!! Beautiful 3 bed home...steps from beach!, holiday rental in Gloucester

Newly Renovated!! Beautiful 3 bed home...steps from beach!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Oceanfront Home in Estate Setting in Gloucester, holiday rental in Gloucester

Beautiful Oceanfront Home in Estate Setting in Gloucester

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Perfect Good Harbor Beach vacation home for large and/or extended family getaway, holiday rental in Gloucester

Perfect Good Harbor Beach vacation home for large and/or extended family getaway

5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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4 Bedroom LUX House/with Pool Next Door, holiday rental in Gloucester

4 Bedroom LUX House/with Pool Next Door

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking, holiday rental in Gloucester

Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, holiday rental in Gloucester

Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Long Beach-Gloucester-1 minute walk to Beach Lovely setting & big yard. Sleeps 6, holiday rental in Gloucester

Long Beach-Gloucester-1 minute walk to Beach Lovely setting & big yard. Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to Good Harbor Beach, pet friendly, family beach home, holiday rental in Gloucester

Walk to Good Harbor Beach, pet friendly, family beach home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Romantic SUMMERWIND COTTAGE- Scenic Harbor View, holiday rental in Gloucester

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach, holiday rental in Gloucester

Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!, holiday rental in Gloucester

Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Walk to downtown Gloucester & Pavilion Beach!, holiday rental in Gloucester

Walk to downtown Gloucester & Pavilion Beach!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean, holiday rental in Gloucester

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning SUNSET STUDIO w/Scenic Harbor View, holiday rental in Gloucester

Stunning SUNSET STUDIO w/Scenic Harbor View

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Haabah--NEW!--Retreat on Good Harbor Beach, holiday rental in Gloucester

The Haabah--NEW!--Retreat on Good Harbor Beach

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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La Bohème RETREAT Studio, holiday rental in Gloucester

La Bohème RETREAT Studio

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Welcoming Getway Oasis, holiday rental in Gloucester

Welcoming Getway Oasis

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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At the Footbridge entrance to Good Harbor Beach, holiday rental in Gloucester

At the Footbridge entrance to Good Harbor Beach

6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Coastal, Cute & Cozy|Close to Everything, holiday rental in Gloucester

Coastal, Cute & Cozy|Close to Everything

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lovely 'Blue Heron Cottage' on Annisquam River!, holiday rental in Gloucester

Lovely 'Blue Heron Cottage' on Annisquam River!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA, holiday rental in Gloucester

Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage at the Cove: A delightful vacation home close to Plum Cove Beach., holiday rental in Gloucester

Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cedar Ledge Annisquam: Ocean views & traditional New England charm., holiday rental in Gloucester

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

6 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach., holiday rental in Gloucester

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Magnolia Tides: Multi-level waterfront home, holiday rental in Gloucester

Magnolia Tides: Multi-level waterfront home

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Wonder, holiday rental in Gloucester

Waterfront Wonder

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches, holiday rental in Gloucester

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom), holiday rental in Gloucester

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Helena House: European flair, close to Plum Cove Beach., holiday rental in Gloucester

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

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach, holiday rental in Gloucester

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

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Rockwood Cottage, holiday rental in Gloucester

Rockwood Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf, holiday rental in Gloucester

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Annisquam Singing Pines: Private riverfront setting & tidal dock., holiday rental in Gloucester

Annisquam Singing Pines: Private riverfront setting & tidal dock.

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Bell View: Private tennis court and an in-law suite., holiday rental in Gloucester

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

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
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Sunset Cove: Waterfront home in Goose Cove section of Gloucester, holiday rental in Gloucester

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Seaside House: Good Harbor Beach and the Back Shore right outside your door., holiday rental in Gloucester

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

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Long Beach House: Large, comfortable home just 285 feet from the white sands!, holiday rental in Gloucester

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

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Long Beach and Good Harbor Beach summer rental - Gloucester, MA, holiday rental in Gloucester

Long Beach and Good Harbor Beach summer rental - Gloucester, MA

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Perrywinkle: Waterfront on Gloucester’s Rocky Neck., holiday rental in Gloucester

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe., holiday rental in Gloucester

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Elegant And Expansive Victorian Home -- Weekly Summer, Thanksgiving or Christmas, holiday rental in Gloucester

Elegant And Expansive Victorian Home -- Weekly Summer, Thanksgiving or Christmas

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Thurston Point: Waterfront rental with deepwater dock on Annisquam River!, holiday rental in Gloucester

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

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Bray Cottage: A charming cottage close to Wingaersheek Beach., holiday rental in Gloucester

Bray Cottage: A charming cottage close to Wingaersheek Beach.

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!, holiday rental in Gloucester

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beach Walk: Good Harbor Beach footbridge just steps away!, holiday rental in Gloucester

Beach Walk: Good Harbor Beach footbridge just steps away!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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