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Gloucester House Rentals

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128 rentals in Gloucester.
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Good Harbor Beach House, vacation rental in Gloucester
Good Harbor Beach House, vacation rental in Gloucester
Good Harbor Beach House, vacation rental in Gloucester

Good Harbor Beach House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, vacation rental in Gloucester
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, vacation rental in Gloucester
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, vacation rental in Gloucester

WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Sunset Views, Waterfront Property, Dock - Sleeps 12, vacation rental in Gloucester
Sunset Views, Waterfront Property, Dock - Sleeps 12, vacation rental in Gloucester
Sunset Views, Waterfront Property, Dock - Sleeps 12, vacation rental in Gloucester

Sunset Views, Waterfront Property, Dock - Sleeps 12

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
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Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, vacation rental in Gloucester
Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, vacation rental in Gloucester
Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, vacation rental in Gloucester

Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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4 Bedroom LUX House/with Pool Next Door, vacation rental in Gloucester
4 Bedroom LUX House/with Pool Next Door, vacation rental in Gloucester
4 Bedroom LUX House/with Pool Next Door, vacation rental in Gloucester

4 Bedroom LUX House/with Pool Next Door

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Good Harbor Beach House - Walk to Shops, vacation rental in Gloucester
Good Harbor Beach House - Walk to Shops, vacation rental in Gloucester
Good Harbor Beach House - Walk to Shops, vacation rental in Gloucester

Good Harbor Beach House - Walk to Shops

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
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Newly Renovated!! Beautiful 3 bed home...steps from beach!, vacation rental in Gloucester
Newly Renovated!! Beautiful 3 bed home...steps from beach!, vacation rental in Gloucester
Newly Renovated!! Beautiful 3 bed home...steps from beach!, vacation rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE, vacation rental in Gloucester
Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE, vacation rental in Gloucester
Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE, vacation rental in Gloucester

Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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Perfect Good Harbor Beach vacation home for large and/or extended family getaway, vacation rental in Gloucester
Perfect Good Harbor Beach vacation home for large and/or extended family getaway, vacation rental in Gloucester
Perfect Good Harbor Beach vacation home for large and/or extended family getaway, vacation 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
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Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, vacation rental in Gloucester
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, vacation rental in Gloucester
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, vacation rental in Gloucester

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, vacation rental in Gloucester
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, vacation rental in Gloucester
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, vacation rental in Gloucester

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
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BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak, vacation rental in Gloucester
BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak, vacation rental in Gloucester
BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak, vacation rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
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Cape Ann, Annisquam panoramic ocean views from every room., vacation rental in Gloucester
Cape Ann, Annisquam panoramic ocean views from every room., vacation rental in Gloucester
Cape Ann, Annisquam panoramic ocean views from every room., vacation rental in Gloucester

Cape Ann, Annisquam panoramic ocean views from every room.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
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*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, vacation rental in Gloucester
*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, vacation rental in Gloucester
*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, vacation rental in Gloucester

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
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Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), vacation rental in Gloucester
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), vacation rental in Gloucester
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), vacation rental in Gloucester

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
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Walk to Good Harbor Beach, pet friendly, family beach home, vacation rental in Gloucester
Walk to Good Harbor Beach, pet friendly, family beach home, vacation rental in Gloucester
Walk to Good Harbor Beach, pet friendly, family beach home, vacation rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, vacation rental in Gloucester
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, vacation rental in Gloucester
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, vacation rental in Gloucester

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

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Good Harbor Beachfront at the Footbridge, vacation rental in Gloucester
Good Harbor Beachfront at the Footbridge, vacation rental in Gloucester
Good Harbor Beachfront at the Footbridge, vacation rental in Gloucester

Good Harbor Beachfront at the Footbridge

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Waterfront Home with Spectacular Viewsof the Annisquam River, vacation rental in Gloucester
Waterfront Home with Spectacular Viewsof the Annisquam River, vacation rental in Gloucester
Waterfront Home with Spectacular Viewsof the Annisquam River, vacation rental in Gloucester

Waterfront Home with Spectacular Viewsof the Annisquam River

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
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Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, vacation rental in Gloucester
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, vacation rental in Gloucester
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, vacation rental in Gloucester

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

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Romantic SUMMERWIND COTTAGE- Scenic Harbor View, vacation rental in Gloucester
Romantic SUMMERWIND COTTAGE- Scenic Harbor View, vacation rental in Gloucester
Romantic SUMMERWIND COTTAGE- Scenic Harbor View, vacation rental in Gloucester

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Golden Sands at Good Harbor: Just walk across the street to the beach., vacation rental in Gloucester
Golden Sands at Good Harbor: Just walk across the street to the beach., vacation rental in Gloucester
Golden Sands at Good Harbor: Just walk across the street to the beach., vacation rental in Gloucester

Golden Sands at Good Harbor: Just walk across the street to the beach.

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Long Beach-Gloucester-2 minute walk to Beach Lovely setting & big yard. Sleeps 6, vacation rental in Gloucester
Long Beach-Gloucester-2 minute walk to Beach Lovely setting & big yard. Sleeps 6, vacation rental in Gloucester
Long Beach-Gloucester-2 minute walk to Beach Lovely setting & big yard. Sleeps 6, vacation rental in Gloucester

Long Beach-Gloucester-2 minute walk to Beach Lovely setting & big yard. Sleeps 6

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Beautiful & Modern 4+ Bedroom Annisquam W/ Private Lighthouse Beach Access, vacation rental in Gloucester
Beautiful & Modern 4+ Bedroom Annisquam W/ Private Lighthouse Beach Access, vacation rental in Gloucester
Beautiful & Modern 4+ Bedroom Annisquam W/ Private Lighthouse Beach Access, vacation rental in Gloucester

Beautiful & Modern 4+ Bedroom Annisquam W/ Private Lighthouse Beach Access

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps, Vacation Rental House
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Dock!!  40'  Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM, vacation rental in Gloucester
Dock!!  40'  Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM, vacation rental in Gloucester
Dock!!  40'  Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM, vacation rental in Gloucester

Dock!! 40' Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, vacation rental in Gloucester
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, vacation rental in Gloucester
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, vacation rental in Gloucester

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Grand Family Home Between Good Harbor and Long Beach, vacation rental in Gloucester
Grand Family Home Between Good Harbor and Long Beach, vacation rental in Gloucester
Grand Family Home Between Good Harbor and Long Beach, vacation rental in Gloucester

Grand Family Home Between Good Harbor and Long Beach

Holiday Rental House
8 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps, Vacation Rental House
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Magnolia  Ocean View Cottage, vacation rental in Gloucester
Magnolia  Ocean View Cottage, vacation rental in Gloucester
Magnolia  Ocean View Cottage, vacation rental in Gloucester

Magnolia Ocean View Cottage

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Long Beach House: Large, comfortable home just 285 ft from the white sands!, vacation rental in Gloucester
Long Beach House: Large, comfortable home just 285 ft from the white sands!, vacation rental in Gloucester
Long Beach House: Large, comfortable home just 285 ft from the white sands!, vacation rental in Gloucester

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Spacious Beach House/  Steps to Long Beach and short walk to Good Harbor, vacation rental in Gloucester
Spacious Beach House/  Steps to Long Beach and short walk to Good Harbor, vacation rental in Gloucester
Spacious Beach House/  Steps to Long Beach and short walk to Good Harbor, vacation rental in Gloucester

Spacious Beach House/ Steps to Long Beach and short walk to Good Harbor

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
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Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI, vacation rental in Gloucester
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI, vacation rental in Gloucester
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI, vacation rental in Gloucester

Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Long Beach Private & Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil, vacation rental in Gloucester
Long Beach Private & Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil, vacation rental in Gloucester
Long Beach Private & Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil, vacation rental in Gloucester

Long Beach Private & Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, vacation rental in Gloucester
Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, vacation rental in Gloucester
Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, vacation rental in Gloucester

Enjoy the ambiance of a New England Seaside Getaway, without the crowds!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Vacation Rental House
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Hidden Gem - 3 Minute Walk to Beach, vacation rental in Gloucester
Hidden Gem - 3 Minute Walk to Beach, vacation rental in Gloucester
Hidden Gem - 3 Minute Walk to Beach, vacation rental in Gloucester

Hidden Gem - 3 Minute Walk to Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Two Beaches: Walk to Long Beach or Good Harbor!, vacation rental in Gloucester
Two Beaches: Walk to Long Beach or Good Harbor!, vacation rental in Gloucester
Two Beaches: Walk to Long Beach or Good Harbor!, vacation rental in Gloucester

Two Beaches: Walk to Long Beach or Good Harbor!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA., vacation rental in Gloucester
Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA., vacation rental in Gloucester
Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA., vacation rental in Gloucester

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
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Steps to Downtown Gloucester & A/C throughout the house, vacation rental in Gloucester
Steps to Downtown Gloucester & A/C throughout the house, vacation rental in Gloucester
Steps to Downtown Gloucester & A/C throughout the house, vacation rental in Gloucester

Steps to Downtown Gloucester & A/C throughout the house

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Thurston Point: Waterfront rental with deepwater dock on Annisquam River!, vacation rental in Gloucester
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!, vacation rental in Gloucester
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!, vacation rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach, vacation rental in Gloucester
Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach, vacation rental in Gloucester
Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach, vacation rental in Gloucester

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Wingaersheek Beach - Newly Renovated!, vacation rental in Gloucester
Wingaersheek Beach - Newly Renovated!, vacation rental in Gloucester
Wingaersheek Beach - Newly Renovated!, vacation rental in Gloucester

Wingaersheek Beach - Newly Renovated!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps, Vacation Rental House
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Evensong: Oceanview Retreat with Water Access, vacation rental in Gloucester
Evensong: Oceanview Retreat with Water Access, vacation rental in Gloucester
Evensong: Oceanview Retreat with Water Access, vacation rental in Gloucester

Evensong: Oceanview Retreat with Water Access

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps, Vacation Rental House
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Stanwood Point:  Waterfront cottage with large screened porch, yard and dock, vacation rental in Gloucester
Stanwood Point:  Waterfront cottage with large screened porch, yard and dock, vacation rental in Gloucester
Stanwood Point:  Waterfront cottage with large screened porch, yard and dock, vacation rental in Gloucester

Stanwood Point: Waterfront cottage with large screened porch, yard and dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Private, Single Family Beach House, Right at Good Harbor Beach foot bridge, vacation rental in Gloucester
Private, Single Family Beach House, Right at Good Harbor Beach foot bridge, vacation rental in Gloucester
Private, Single Family Beach House, Right at Good Harbor Beach foot bridge, vacation rental in Gloucester

Private, Single Family Beach House, Right at Good Harbor Beach foot bridge

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Vacation Rental House
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Clean Waterfront Classic Cottage with Private Beach, vacation rental in Gloucester
Clean Waterfront Classic Cottage with Private Beach, vacation rental in Gloucester
Clean Waterfront Classic Cottage with Private Beach, vacation rental in Gloucester

Clean Waterfront Classic Cottage with Private Beach

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps, Vacation Rental House
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Quaint Home, Near Good Harbor Beach and Town, Great for Families, vacation rental in Gloucester
Quaint Home, Near Good Harbor Beach and Town, Great for Families, vacation rental in Gloucester
Quaint Home, Near Good Harbor Beach and Town, Great for Families, vacation rental in Gloucester

Quaint Home, Near Good Harbor Beach and Town, Great for Families

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Vacation Rental House
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Lanesville Cove Retreat Home, vacation rental in Gloucester
Lanesville Cove Retreat Home, vacation rental in Gloucester
Lanesville Cove Retreat Home, vacation rental in Gloucester

Lanesville Cove Retreat Home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach, vacation rental in Gloucester
3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach, vacation rental in Gloucester
3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach, vacation 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, Vacation Rental House
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Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville., vacation rental in Gloucester
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville., vacation rental in Gloucester
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville., vacation 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, Vacation Rental House
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Annisquam Singing Pines: Private riverfront setting & tidal dock., vacation rental in Gloucester
Annisquam Singing Pines: Private riverfront setting & tidal dock., vacation rental in Gloucester
Annisquam Singing Pines: Private riverfront setting & tidal dock., vacation rental in Gloucester

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Pristine Annisquam Beach House, walk to Diamond Cove & Lighthouse Beach, vacation rental in Gloucester
Pristine Annisquam Beach House, walk to Diamond Cove & Lighthouse Beach, vacation rental in Gloucester
Pristine Annisquam Beach House, walk to Diamond Cove & Lighthouse Beach, vacation rental in Gloucester

Pristine Annisquam Beach House, walk to Diamond Cove & Lighthouse Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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