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Holiday Apartments in Gloucester

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136 rentals in Gloucester.
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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
3 bathrooms
Sleeps 8
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
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Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, holiday rental in Gloucester
Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, holiday rental in Gloucester
Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, holiday rental in Gloucester

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, holiday rental in Gloucester
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, holiday rental in Gloucester
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quality Accommodations in Quiet Seaside Village, holiday rental in Gloucester
Quality Accommodations in Quiet Seaside Village, holiday rental in Gloucester
Quality Accommodations in Quiet Seaside Village, holiday rental in Gloucester

Quality Accommodations in Quiet Seaside Village

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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
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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
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Beautiful Oceanfront Home in Estate Setting in Gloucester, holiday rental in Gloucester
Beautiful Oceanfront Home in Estate Setting in Gloucester, holiday rental in Gloucester
Beautiful Oceanfront Home in Estate Setting in Gloucester, holiday rental in Gloucester

Beautiful Oceanfront Home in Estate Setting in Gloucester

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Jul 12-16 OPEN! SUNSET STUDIO w/Scenic Harbor View, holiday rental in Gloucester
Jul 12-16 OPEN! SUNSET STUDIO w/Scenic Harbor View, holiday rental in Gloucester
Jul 12-16 OPEN! SUNSET STUDIO w/Scenic Harbor View, holiday rental in Gloucester

Jul 12-16 OPEN! SUNSET STUDIO w/Scenic Harbor View

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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
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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
1 bathroom
Sleeps 4
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, 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
2 bathrooms
Sleeps 6
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, 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
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Prime Gloucester Property - Overlooking Harbor with Private Pool, holiday rental in Gloucester
Prime Gloucester Property - Overlooking Harbor with Private Pool, holiday rental in Gloucester
Prime Gloucester Property - Overlooking Harbor with Private Pool, holiday rental in Gloucester

Prime Gloucester Property - Overlooking Harbor with Private Pool

Condo/Apartment
2 bedrooms
2 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
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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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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
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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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, holiday rental in Gloucester
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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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
3 bathrooms
Sleeps 11
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
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Long Beach-Gloucester-2 minute walk to Beach Lovely setting & big yard. Sleeps 6, holiday rental in Gloucester
Long Beach-Gloucester-2 minute walk to Beach Lovely setting & big yard. Sleeps 6, holiday rental in Gloucester
Long Beach-Gloucester-2 minute walk to Beach Lovely setting & big yard. Sleeps 6, holiday 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
More info
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A tranquil ocean retreat steps from the water's edge, holiday rental in Gloucester
A tranquil ocean retreat steps from the water's edge, holiday rental in Gloucester
A tranquil ocean retreat steps from the water's edge, holiday rental in Gloucester

A tranquil ocean retreat steps from the water's edge

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Waterfront Home with Spectacular Viewsof the Annisquam River, holiday rental in Gloucester
Waterfront Home with Spectacular Viewsof the Annisquam River, holiday rental in Gloucester
Waterfront Home with Spectacular Viewsof the Annisquam River, holiday rental in Gloucester

Waterfront Home with Spectacular Viewsof the Annisquam River

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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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, holiday rental in Gloucester
Walk to Good Harbor Beach, pet friendly, family beach home, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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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
More info
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Golden Sands at Good Harbor: Just walk across the street to the beach., holiday rental in Gloucester
Golden Sands at Good Harbor: Just walk across the street to the beach., holiday rental in Gloucester
Golden Sands at Good Harbor: Just walk across the street to the beach., holiday 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
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
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Long Beach House: Large, comfortable home just 285 ft from the white sands!, holiday rental in Gloucester
Long Beach House: Large, comfortable home just 285 ft from the white sands!, holiday rental in Gloucester
Long Beach House: Large, comfortable home just 285 ft from the white sands!, holiday 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
More info
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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!, holiday rental in Gloucester
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!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
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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Grand Family Home Between Good Harbor and Long Beach, holiday rental in Gloucester
Grand Family Home Between Good Harbor and Long Beach, holiday rental in Gloucester
Grand Family Home Between Good Harbor and Long Beach, holiday rental in Gloucester

Grand Family Home Between Good Harbor and Long Beach

Holiday Rental House
8 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
More info
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Magnolia  Ocean View Cottage, holiday rental in Gloucester
Magnolia  Ocean View Cottage, holiday rental in Gloucester
Magnolia  Ocean View Cottage, holiday rental in Gloucester

Magnolia Ocean View Cottage

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Steps to Downtown Gloucester & A/C throughout the house, holiday rental in Gloucester
Steps to Downtown Gloucester & A/C throughout the house, holiday rental in Gloucester
Steps to Downtown Gloucester & A/C throughout the house, holiday rental in Gloucester

Steps to Downtown Gloucester & A/C throughout the house

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Wingaersheek Beach - Newly Renovated!, holiday rental in Gloucester
Wingaersheek Beach - Newly Renovated!, holiday rental in Gloucester
Wingaersheek Beach - Newly Renovated!, holiday rental in Gloucester

Wingaersheek Beach - Newly Renovated!

Holiday Rental House
2 bedrooms
2 bathrooms
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
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Annisquam Bridge House at Lobster Cove. Booking fall/winter, holiday rental in Gloucester
Annisquam Bridge House at Lobster Cove. Booking fall/winter, holiday rental in Gloucester
Annisquam Bridge House at Lobster Cove. Booking fall/winter, holiday rental in Gloucester

Annisquam Bridge House at Lobster Cove. Booking fall/winter

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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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
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Dock!!  40'  Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM, holiday rental in Gloucester
Dock!!  40'  Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM, holiday rental in Gloucester
Dock!!  40'  Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM, holiday 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
More info
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Clean Waterfront Classic Cottage with Private Beach, holiday rental in Gloucester
Clean Waterfront Classic Cottage with Private Beach, holiday rental in Gloucester
Clean Waterfront Classic Cottage with Private Beach, holiday rental in Gloucester

Clean Waterfront Classic Cottage with Private Beach

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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La Bohème RETREAT - UNPLUG, UNWIND & UPLIFT your spirits!, holiday rental in Gloucester
La Bohème RETREAT - UNPLUG, UNWIND & UPLIFT your spirits!, holiday rental in Gloucester
La Bohème RETREAT - UNPLUG, UNWIND & UPLIFT your spirits!, holiday rental in Gloucester

La Bohème RETREAT - UNPLUG, UNWIND & UPLIFT your spirits!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Stanwood Point:  Waterfront cottage with large screened porch, yard and dock, holiday rental in Gloucester
Stanwood Point:  Waterfront cottage with large screened porch, yard and dock, holiday rental in Gloucester
Stanwood Point:  Waterfront cottage with large screened porch, yard and dock, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ocean front and 3 beaches across the st,parks, short walk to historic downtown, holiday rental in Gloucester
Ocean front and 3 beaches across the st,parks, short walk to historic downtown, holiday rental in Gloucester
Ocean front and 3 beaches across the st,parks, short walk to historic downtown, holiday rental in Gloucester

Ocean front and 3 beaches across the st,parks, short walk to historic downtown

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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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, holiday rental in Gloucester
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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Evensong: Oceanview Retreat with Water Access, holiday rental in Gloucester
Evensong: Oceanview Retreat with Water Access, holiday rental in Gloucester
Evensong: Oceanview Retreat with Water Access, holiday rental in Gloucester

Evensong: Oceanview Retreat with Water Access

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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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, holiday rental in Gloucester
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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
More info
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