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Gloucester Holiday Apartments

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123 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
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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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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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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
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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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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 4
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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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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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
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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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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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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
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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 w Pool, holiday rental in Gloucester
Prime Gloucester Property - Overlooking Harbor w Pool, holiday rental in Gloucester
Prime Gloucester Property - Overlooking Harbor w Pool, holiday rental in Gloucester

Prime Gloucester Property - Overlooking Harbor w Pool

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

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

Condo/Apartment
3 bedrooms
1 bathroom
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
3 bathrooms
Sleeps 11
Match: Sleeps
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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
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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, holiday rental in Gloucester
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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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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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
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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
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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
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SERENITY BY THE SEA - GLOUCESTER, MA, holiday rental in Gloucester
SERENITY BY THE SEA - GLOUCESTER, MA, holiday rental in Gloucester
SERENITY BY THE SEA - GLOUCESTER, MA, holiday rental in Gloucester

SERENITY BY THE SEA - GLOUCESTER, MA

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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
3 bathrooms
Sleeps 10
Match: Sleeps
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Seaside Village of Lanesville - North Gloucester, MA

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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
4 bathrooms
Sleeps 12
Match: Sleeps
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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
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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
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La Bohème RETREAT  - UNPLUG, UNWIND & UPLIFT your spirit!, holiday rental in Gloucester
La Bohème RETREAT  - UNPLUG, UNWIND & UPLIFT your spirit!, holiday rental in Gloucester
La Bohème RETREAT  - UNPLUG, UNWIND & UPLIFT your spirit!, holiday rental in Gloucester

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

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

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

Welcoming Getway Oasis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Annisquam Bridge House at Lobster Cove., holiday rental in Gloucester
Annisquam Bridge House at Lobster Cove., holiday rental in Gloucester
Annisquam Bridge House at Lobster Cove., holiday rental in Gloucester

Annisquam Bridge House at Lobster Cove.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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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Plaisance - a summer vacation rental near Bass Rocks, holiday rental in Gloucester
Plaisance - a summer vacation rental near Bass Rocks, holiday rental in Gloucester
Plaisance - a summer vacation rental near Bass Rocks, holiday rental in Gloucester

Plaisance - a summer vacation rental near Bass Rocks

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
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Lanesville Cove Retreat Home, holiday rental in Gloucester
Lanesville Cove Retreat Home, holiday rental in Gloucester
Lanesville Cove Retreat Home, holiday rental in Gloucester

Lanesville Cove Retreat Home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Pristine Annisquam Beach House, walk to Diamond Cove & Lighthouse Beach, holiday rental in Gloucester
Pristine Annisquam Beach House, walk to Diamond Cove & Lighthouse Beach, holiday rental in Gloucester
Pristine Annisquam Beach House, walk to Diamond Cove & Lighthouse Beach, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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, holiday rental in Gloucester
The Haabah--NEW!--Retreat on Good Harbor Beach, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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