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Holiday Rentals in Gloucester

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
202 rentals in Gloucester.
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
More info
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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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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
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Romantic Summerwind Cottage,  Harbor View w/Large Deck, holiday rental in Gloucester
Romantic Summerwind Cottage,  Harbor View w/Large Deck, holiday rental in Gloucester
Romantic Summerwind Cottage,  Harbor View w/Large Deck, holiday rental in Gloucester

Romantic Summerwind Cottage, Harbor View w/Large Deck

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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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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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Luxury Accommodations in Quiet Seaside Village, holiday rental in Gloucester
Luxury Accommodations in Quiet Seaside Village, holiday rental in Gloucester
Luxury Accommodations in Quiet Seaside Village, holiday rental in Gloucester

Luxury Accommodations in Quiet Seaside Village

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

Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, holiday rental in Gloucester
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, holiday rental in Gloucester
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, holiday rental in Gloucester

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

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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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 12
Match: Sleeps
More info
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25% DISCOUNT - Private 2-Acre Retreat - MODERN 4 Bedrooms- See Video Tour, holiday rental in Gloucester
25% DISCOUNT - Private 2-Acre Retreat - MODERN 4 Bedrooms- See Video Tour, holiday rental in Gloucester
25% DISCOUNT - Private 2-Acre Retreat - MODERN 4 Bedrooms- See Video Tour, holiday rental in Gloucester

25% DISCOUNT - 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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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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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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Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, holiday rental in Gloucester
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, holiday rental in Gloucester
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, holiday rental in Gloucester

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

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
More info
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Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6, holiday rental in Gloucester
Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6, holiday rental in Gloucester
Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6, holiday rental in Gloucester

Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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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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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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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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Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, holiday rental in Gloucester
Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, holiday rental in Gloucester
Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, holiday 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
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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Good Harbor Beachfront at the Footbridge, holiday rental in Gloucester
Good Harbor Beachfront at the Footbridge, holiday rental in Gloucester
Good Harbor Beachfront at the Footbridge, holiday rental in Gloucester

Good Harbor Beachfront at the Footbridge

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 10
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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Payment Protection
Walk to Good Harbor Beach 6/10 mile., holiday rental in Gloucester
Walk to Good Harbor Beach 6/10 mile., holiday rental in Gloucester
Walk to Good Harbor Beach 6/10 mile., holiday rental in Gloucester

Walk to Good Harbor Beach 6/10 mile.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Ocean and Woods! Best of both seaside delights in Gloucester!, holiday rental in Gloucester
Ocean and Woods! Best of both seaside delights in Gloucester!, holiday rental in Gloucester
Ocean and Woods! Best of both seaside delights in Gloucester!, holiday rental in Gloucester

Ocean and Woods! Best of both seaside delights in Gloucester!

Condo/Apartment
2 bedrooms
1 bathroom
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
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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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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Spacious Beach House/  Steps to Long Beach and short walk to Good Harbor, holiday rental in Gloucester
Spacious Beach House/  Steps to Long Beach and short walk to Good Harbor, holiday rental in Gloucester
Spacious Beach House/  Steps to Long Beach and short walk to Good Harbor, holiday 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
Match: Sleeps
More info
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Hidden Gem - 3 Minute Walk to Beach, holiday rental in Gloucester
Hidden Gem - 3 Minute Walk to Beach, holiday rental in Gloucester
Hidden Gem - 3 Minute Walk to Beach, holiday rental in Gloucester

Hidden Gem - 3 Minute Walk to Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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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Beautiful & Modern 4+ Bedroom Annisquam W/ Private Lighthouse Beach Access, holiday rental in Gloucester
Beautiful & Modern 4+ Bedroom Annisquam W/ Private Lighthouse Beach Access, holiday rental in Gloucester
Beautiful & Modern 4+ Bedroom Annisquam W/ Private Lighthouse Beach Access, holiday rental in Gloucester

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

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 15
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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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
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil, holiday rental in Gloucester
Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil, holiday rental in Gloucester
Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil, holiday rental in Gloucester

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

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 15
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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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
More info
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Seaside Village of Lanesville - North Gloucester, MA, holiday rental in Gloucester
Seaside Village of Lanesville - North Gloucester, MA, holiday rental in Gloucester
Seaside Village of Lanesville - North Gloucester, MA, holiday rental in Gloucester

Seaside Village of Lanesville - North Gloucester, MA

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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VIEWS! Annisquam Bridge House at Lobster Cove. JUNE SPECIAL RATES, holiday rental in Gloucester
VIEWS! Annisquam Bridge House at Lobster Cove. JUNE SPECIAL RATES, holiday rental in Gloucester
VIEWS! Annisquam Bridge House at Lobster Cove. JUNE SPECIAL RATES, holiday rental in Gloucester

VIEWS! Annisquam Bridge House at Lobster Cove. JUNE SPECIAL RATES

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI, holiday rental in Gloucester
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI, holiday rental in Gloucester
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI, holiday 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
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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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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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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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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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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Showing results 1-50 of 202
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