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Holiday Rentals in Gloucester

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172 rentals in Gloucester.
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Romantic SUMMERWIND COTTAGE- Scenic Harbor View, holiday rental in Gloucester
Romantic SUMMERWIND COTTAGE- Scenic Harbor View, holiday rental in Gloucester
Romantic SUMMERWIND COTTAGE- Scenic Harbor View, holiday rental in Gloucester

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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, holiday rental in Gloucester
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches, holiday rental in Gloucester

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bohemia RETREAT Studio, holiday rental in Gloucester
Bohemia RETREAT Studio, holiday rental in Gloucester
Bohemia RETREAT Studio, holiday rental in Gloucester

Bohemia RETREAT Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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!, holiday rental in Gloucester
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!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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., holiday rental in Gloucester
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.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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!, holiday rental in Gloucester
Beach Walk: Good Harbor Beach footbridge just steps away!, holiday rental in Gloucester

Beach Walk: Good Harbor Beach footbridge just steps away!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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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!, holiday rental in Gloucester
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!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
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, holiday rental in Gloucester
At the Footbridge entrance to Good Harbor Beach, holiday rental in Gloucester

At the Footbridge entrance to Good Harbor Beach

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Golden Sands at Good Harbor: Across the street from the beach, holiday rental in Gloucester
Golden Sands at Good Harbor: Across the street from the beach, holiday rental in Gloucester
Golden Sands at Good Harbor: Across the street from the beach, holiday rental in Gloucester

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

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 12
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., holiday rental in Gloucester
Annisquam Singing Pines: Private riverfront setting & tidal dock., holiday rental in Gloucester

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sea Fox: Custom-designed home with rights to private Coffins Beach, holiday rental in Gloucester
Sea Fox: Custom-designed home with rights to private Coffins Beach, holiday rental in Gloucester
Sea Fox: Custom-designed home with rights to private Coffins Beach, holiday rental in Gloucester

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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., holiday rental in Gloucester
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.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Woodsy 3BR Cottage, holiday rental in Gloucester
Waterfront Woodsy 3BR Cottage, holiday rental in Gloucester
Waterfront Woodsy 3BR Cottage, holiday rental in Gloucester

Waterfront Woodsy 3BR Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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., holiday rental in Gloucester
Helena House: European flair, close to Plum Cove Beach., holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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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., holiday rental in Gloucester
Bell View: Private tennis court and an in-law suite., holiday rental in Gloucester

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

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Magnolia Tides: Multi-level waterfront home, holiday rental in Gloucester
Magnolia Tides: Multi-level waterfront home, holiday rental in Gloucester
Magnolia Tides: Multi-level waterfront home, holiday rental in Gloucester

Magnolia Tides: Multi-level waterfront home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
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!, holiday rental in Gloucester
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Two Beaches: Walk to Long Beach or Good Harbor!, holiday rental in Gloucester
Two Beaches: Walk to Long Beach or Good Harbor!, holiday rental in Gloucester
Two Beaches: Walk to Long Beach or Good Harbor!, holiday rental in Gloucester

Two Beaches: Walk to Long Beach or Good Harbor!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville., holiday rental in Gloucester
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville., holiday rental in Gloucester
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville., holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, holiday rental in Gloucester
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, holiday rental in Gloucester
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, holiday rental in Gloucester

Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
More info
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Cozy, Waterview Old Quarryman boarding house, holiday rental in Gloucester
Cozy, Waterview Old Quarryman boarding house, holiday rental in Gloucester
Cozy, Waterview Old Quarryman boarding house, holiday rental in Gloucester

Cozy, Waterview Old Quarryman boarding house

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Prime Gloucester Property Overlooking Inner Harbor, holiday rental in Gloucester
Prime Gloucester Property Overlooking Inner Harbor, holiday rental in Gloucester
Prime Gloucester Property Overlooking Inner Harbor, holiday rental in Gloucester

Prime Gloucester Property Overlooking Inner Harbor

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Walk to Good Harbor Beach 6/10 mile. 2 adults , 2 children, holiday rental in Gloucester
Walk to Good Harbor Beach 6/10 mile. 2 adults , 2 children, holiday rental in Gloucester
Walk to Good Harbor Beach 6/10 mile. 2 adults , 2 children, holiday rental in Gloucester

Walk to Good Harbor Beach 6/10 mile. 2 adults , 2 children

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA., holiday rental in Gloucester
Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA., holiday rental in Gloucester
Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA., holiday rental in Gloucester

Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA.

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Gloucester
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

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
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3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach, holiday rental in Gloucester
3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach, holiday rental in Gloucester
3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach, holiday rental in Gloucester

3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Good Harbor Beach House, holiday rental in Gloucester
Good Harbor Beach House, holiday rental in Gloucester
Good Harbor Beach House, holiday rental in Gloucester

Good Harbor Beach House

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Good Harbor Beach House - Walk to Shops, holiday rental in Gloucester
Good Harbor Beach House - Walk to Shops, holiday rental in Gloucester
Good Harbor Beach House - Walk to Shops, holiday rental in Gloucester

Good Harbor Beach House - Walk to Shops

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Cape Ann, Annisquam panoramic ocean views from every room., holiday rental in Gloucester
Cape Ann, Annisquam panoramic ocean views from every room., holiday rental in Gloucester
Cape Ann, Annisquam panoramic ocean views from every room., holiday rental in Gloucester

Cape Ann, Annisquam panoramic ocean views from every room.

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, holiday rental in Gloucester
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, holiday rental in Gloucester
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, holiday rental in Gloucester

Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
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2 Bedroom Waterfront Unit, Vacation or Short Term Rental, holiday rental in Gloucester
2 Bedroom Waterfront Unit, Vacation or Short Term Rental, holiday rental in Gloucester
2 Bedroom Waterfront Unit, Vacation or Short Term Rental, holiday rental in Gloucester

2 Bedroom Waterfront Unit, Vacation or Short Term Rental

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), holiday rental in Gloucester
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), holiday rental in Gloucester
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), holiday rental in Gloucester

Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester)

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
More info
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GOT BEACH!  Good Harbor House, holiday rental in Gloucester
GOT BEACH!  Good Harbor House, holiday rental in Gloucester
GOT BEACH!  Good Harbor House, holiday rental in Gloucester

GOT BEACH! Good Harbor House

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sunset Views, Waterfront Property, Dock - Sleeps 12, holiday rental in Gloucester
Sunset Views, Waterfront Property, Dock - Sleeps 12, holiday rental in Gloucester
Sunset Views, Waterfront Property, Dock - Sleeps 12, holiday rental in Gloucester

Sunset Views, Waterfront Property, Dock - Sleeps 12

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks Mins Away, holiday rental in Gloucester
Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks Mins Away, holiday rental in Gloucester
Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks Mins Away, holiday rental in Gloucester

Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks Mins Away

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, holiday rental in Gloucester
*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, holiday rental in Gloucester
*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, holiday rental in Gloucester

*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Seaside Village of Lanesville - North Gloucester, MA

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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!, holiday rental in Gloucester
Newly Renovated!! Beautiful 3 bed home...steps from beach!, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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, holiday rental in Gloucester
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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
More info
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Salt Island Views: Walking distance to Good Harbor & Long Beach., holiday rental in Gloucester
Salt Island Views: Walking distance to Good Harbor & Long Beach., holiday rental in Gloucester
Salt Island Views: Walking distance to Good Harbor & Long Beach., holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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), holiday rental in Gloucester
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)

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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, holiday rental in Gloucester
Sunset Cove: Waterfront home in Goose Cove section of Gloucester, holiday rental in Gloucester

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Perrywinkle: Waterfront on Gloucester’s Rocky Neck., holiday rental in Gloucester
Perrywinkle: Waterfront on Gloucester’s Rocky Neck., holiday rental in Gloucester
Perrywinkle: Waterfront on Gloucester’s Rocky Neck., holiday rental in Gloucester

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Stunning SUNSET STUDIO w/Scenic Harbor View, holiday rental in Gloucester
Stunning SUNSET STUDIO w/Scenic Harbor View, holiday rental in Gloucester
Stunning SUNSET STUDIO w/Scenic Harbor View, holiday rental in Gloucester

Stunning SUNSET STUDIO w/Scenic Harbor View

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

Lovely 'Blue Heron Cottage' on Annisquam River!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Elegant Gloucester Beach Getaway with Ocean Views!, holiday rental in Gloucester
Elegant Gloucester Beach Getaway with Ocean Views!, holiday rental in Gloucester
Elegant Gloucester Beach Getaway with Ocean Views!, holiday rental in Gloucester

Elegant Gloucester Beach Getaway with Ocean Views!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Family Tides: Only a half-mile from Good Harbor Beach., holiday rental in Gloucester
Family Tides: Only a half-mile from Good Harbor Beach., holiday rental in Gloucester
Family Tides: Only a half-mile from Good Harbor Beach., holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Coastal, Cute & Cozy|Close to Everything, holiday rental in Gloucester
Coastal, Cute & Cozy|Close to Everything, holiday rental in Gloucester
Coastal, Cute & Cozy|Close to Everything, holiday rental in Gloucester

Coastal, Cute & Cozy|Close to Everything

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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, holiday rental in Gloucester
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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4 Bedroom LUX House/with Pool Next Door, holiday rental in Gloucester
4 Bedroom LUX House/with Pool Next Door, holiday rental in Gloucester
4 Bedroom LUX House/with Pool Next Door, holiday rental in Gloucester

4 Bedroom LUX House/with Pool Next Door

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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