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Holiday Rentals in Gloucester

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
182 rentals in Gloucester.
Coastal, Cute & Cozy|Close to Everything, holiday rental in Gloucester
Coastal, Cute & Cozy|Close to Everything, holiday rental in Gloucester
Coastal, Cute & Cozy|Close to Everything, holiday rental in Gloucester

Coastal, Cute & Cozy|Close to Everything

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Payment Protection
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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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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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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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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Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat, holiday rental in Gloucester
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat, holiday rental in Gloucester
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat, holiday rental in Gloucester

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
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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Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks, holiday rental in Gloucester
Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks, holiday rental in Gloucester
Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks, holiday rental in Gloucester

Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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The Duval House, holiday rental in Gloucester
The Duval House, holiday rental in Gloucester
The Duval House, holiday rental in Gloucester

The Duval House

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Newly Renovated Family Getaway, Walk to Harbor, Beach, and Downtown, holiday rental in Gloucester
Newly Renovated Family Getaway, Walk to Harbor, Beach, and Downtown, holiday rental in Gloucester
Newly Renovated Family Getaway, Walk to Harbor, Beach, and Downtown, holiday rental in Gloucester

Newly Renovated Family Getaway, Walk to Harbor, Beach, and Downtown

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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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Cozy spacious home - Walk to both Good Harbor Beach and Long Beach, & Rockport, holiday rental in Gloucester
Cozy spacious home - Walk to both Good Harbor Beach and Long Beach, & Rockport, holiday rental in Gloucester
Cozy spacious home - Walk to both Good Harbor Beach and Long Beach, & Rockport, holiday rental in Gloucester

Cozy spacious home - Walk to both Good Harbor Beach and Long Beach, & Rockport

Holiday Rental House
5 bedrooms
2 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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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 1900's romantic retreat steps from the beach, holiday rental in Gloucester
Luxury 1900's romantic retreat steps from the beach, holiday rental in Gloucester
Luxury 1900's romantic retreat steps from the beach, holiday rental in Gloucester

Luxury 1900's romantic retreat steps from the beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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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Steps to Wingaersheek's Private 1.5 Mile White Dune Beach, holiday rental in Gloucester
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach, holiday rental in Gloucester
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach, holiday rental in Gloucester

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Classic charmer near the coast with with a firepit, outdoor shower, & beach gear, holiday rental in Gloucester
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear, holiday rental in Gloucester
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear, holiday rental in Gloucester

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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WALK TO BEACH! Convenient location! Beautifully updated! Sept-Dec Availability!, holiday rental in Gloucester
WALK TO BEACH! Convenient location! Beautifully updated! Sept-Dec Availability!, holiday rental in Gloucester
WALK TO BEACH! Convenient location! Beautifully updated! Sept-Dec Availability!, holiday rental in Gloucester

WALK TO BEACH! Convenient location! Beautifully updated! Sept-Dec Availability!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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NEW 3BR/2 BA Harborside Home · Backyard+Grill · Ocean Views, holiday rental in Gloucester
NEW 3BR/2 BA Harborside Home · Backyard+Grill · Ocean Views, holiday rental in Gloucester
NEW 3BR/2 BA Harborside Home · Backyard+Grill · Ocean Views, holiday rental in Gloucester

NEW 3BR/2 BA Harborside Home · Backyard+Grill · Ocean Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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Check-out
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First Period Colonial Lodging in Gloucester MA, holiday rental in Gloucester
First Period Colonial Lodging in Gloucester MA, holiday rental in Gloucester
First Period Colonial Lodging in Gloucester MA, holiday rental in Gloucester

First Period Colonial Lodging in Gloucester MA

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Check-out
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Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar, holiday rental in Gloucester
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar, holiday rental in Gloucester
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar, holiday rental in Gloucester

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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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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Check-out
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Coastal retreat steps to the beach with streaming, washer/dryer, desk, & AC, holiday rental in Gloucester
Coastal retreat steps to the beach with streaming, washer/dryer, desk, & AC, holiday rental in Gloucester
Coastal retreat steps to the beach with streaming, washer/dryer, desk, & AC, holiday rental in Gloucester

Coastal retreat steps to the beach with streaming, washer/dryer, desk, & AC

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Check-out
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Little River+Annisquam River access; rivers views from screenporch, deck, KingBR, holiday rental in Gloucester
Little River+Annisquam River access; rivers views from screenporch, deck, KingBR, holiday rental in Gloucester
Little River+Annisquam River access; rivers views from screenporch, deck, KingBR, holiday rental in Gloucester

Little River+Annisquam River access; rivers views from screenporch, deck, KingBR

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Check-out
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Long Beach Suites: Ocean Views, Walk To Beach, holiday rental in Gloucester
Long Beach Suites: Ocean Views, Walk To Beach, holiday rental in Gloucester
Long Beach Suites: Ocean Views, Walk To Beach, holiday rental in Gloucester

Long Beach Suites: Ocean Views, Walk To Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Charming 1900's historic, colonial escape just steps from the beach, holiday rental in Gloucester
Charming 1900's historic, colonial escape just steps from the beach, holiday rental in Gloucester
Charming 1900's historic, colonial escape just steps from the beach, holiday rental in Gloucester

Charming 1900's historic, colonial escape just steps from the beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Adorable cottage in Gloucester - close to many local hotspots, holiday rental in Gloucester
Adorable cottage in Gloucester - close to many local hotspots, holiday rental in Gloucester
Adorable cottage in Gloucester - close to many local hotspots, holiday rental in Gloucester

Adorable cottage in Gloucester - close to many local hotspots

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Charming Studio, Private Bath, Kitchenette, Deck, Walk to  Beach, holiday rental in Gloucester
Charming Studio, Private Bath, Kitchenette, Deck, Walk to  Beach, holiday rental in Gloucester
Charming Studio, Private Bath, Kitchenette, Deck, Walk to  Beach, holiday rental in Gloucester

Charming Studio, Private Bath, Kitchenette, Deck, Walk to Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Check-out
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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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Summer is still here ..September is the best month of the year here on Cape Ann!, holiday rental in Gloucester
Summer is still here ..September is the best month of the year here on Cape Ann!, holiday rental in Gloucester
Summer is still here ..September is the best month of the year here on Cape Ann!, holiday rental in Gloucester

Summer is still here ..September is the best month of the year here on Cape Ann!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Check-out
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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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Check-out
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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
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Lovely Upstairs Apartment, holiday rental in Gloucester
Lovely Upstairs Apartment, holiday rental in Gloucester
Lovely Upstairs Apartment, holiday rental in Gloucester

Lovely Upstairs Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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A beautiful place by the Sea. 45 min to Boston!, holiday rental in Gloucester
A beautiful place by the Sea. 45 min to Boston!, holiday rental in Gloucester
A beautiful place by the Sea. 45 min to Boston!, holiday rental in Gloucester

A beautiful place by the Sea. 45 min to Boston!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Unobstructed, Direct Ocean Views! Walk to Good Harbor!, holiday rental in Gloucester
Unobstructed, Direct Ocean Views! Walk to Good Harbor!, holiday rental in Gloucester
Unobstructed, Direct Ocean Views! Walk to Good Harbor!, holiday rental in Gloucester

Unobstructed, Direct Ocean Views! Walk to Good Harbor!

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Check-out
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Downtown Dahlias fully remodeled in the heart of Gloucester, holiday rental in Gloucester
Downtown Dahlias fully remodeled in the heart of Gloucester, holiday rental in Gloucester
Downtown Dahlias fully remodeled in the heart of Gloucester, holiday rental in Gloucester

Downtown Dahlias fully remodeled in the heart of Gloucester

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
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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Check-out
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Cozy, Waterview Old Quarryman boarding house, holiday rental in Gloucester
Cozy, Waterview Old Quarryman boarding house, holiday rental in Gloucester
Cozy, Waterview Old Quarryman boarding house, holiday rental in Gloucester

Cozy, Waterview Old Quarryman boarding house

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Check-out
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Long Beach Suites: Ready To Host You This Summer!, holiday rental in Gloucester
Long Beach Suites: Ready To Host You This Summer!, holiday rental in Gloucester
Long Beach Suites: Ready To Host You This Summer!, holiday rental in Gloucester

Long Beach Suites: Ready To Host You This Summer!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Walk to the ocean, very private. Secluded, woodsy location., holiday rental in Gloucester
Walk to the ocean, very private. Secluded, woodsy location., holiday rental in Gloucester
Walk to the ocean, very private. Secluded, woodsy location., holiday rental in Gloucester

Walk to the ocean, very private. Secluded, woodsy location.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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
2 bathrooms
Sleeps 12
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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Lovely 3br apt in Gloucester, free parking, holiday rental in Gloucester
Lovely 3br apt in Gloucester, free parking, holiday rental in Gloucester
Lovely 3br apt in Gloucester, free parking, holiday rental in Gloucester

Lovely 3br apt in Gloucester, free parking

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Long Beach Suites: Book Your Summer Trip Today!, holiday rental in Gloucester
Long Beach Suites: Book Your Summer Trip Today!, holiday rental in Gloucester
Long Beach Suites: Book Your Summer Trip Today!, holiday rental in Gloucester

Long Beach Suites: Book Your Summer Trip Today!

Condo/Apartment
2 bedrooms
1 bathroom
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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Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access, holiday rental in Gloucester
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access, holiday rental in Gloucester
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access, holiday rental in Gloucester

Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Private Beach, Best Beach House in Gloucester!, holiday rental in Gloucester
Private Beach, Best Beach House in Gloucester!, holiday rental in Gloucester
Private Beach, Best Beach House in Gloucester!, holiday rental in Gloucester

Private Beach, Best Beach House in Gloucester!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Walk to Good Harbor and Long Beach -Vacation Home, holiday rental in Gloucester
Walk to Good Harbor and Long Beach -Vacation Home, holiday rental in Gloucester
Walk to Good Harbor and Long Beach -Vacation Home, holiday rental in Gloucester

Walk to Good Harbor and Long Beach -Vacation Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Frequently Asked Questions about Gloucester