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Cheap Gloucester Holiday Homes

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192 rentals 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 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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Too many guests for Thanksgiving? Consider our cozy spacious family home!, holiday rental in Gloucester
Too many guests for Thanksgiving? Consider our cozy spacious family home!, holiday rental in Gloucester
Too many guests for Thanksgiving? Consider our cozy spacious family home!, holiday rental in Gloucester

Too many guests for Thanksgiving? Consider our cozy spacious family home!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury 1900's romantic retreat steps from the beach - King Suite!, holiday rental in Gloucester
Luxury 1900's romantic retreat steps from the beach - King Suite!, holiday rental in Gloucester
Luxury 1900's romantic retreat steps from the beach - King Suite!, holiday rental in Gloucester

Luxury 1900's romantic retreat steps from the beach - King Suite!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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
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3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views, holiday rental in Gloucester
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views, holiday rental in Gloucester
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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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
3 bathrooms
Sleeps 8
Match: Sleeps
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Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, holiday rental in Gloucester
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, holiday rental in Gloucester
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, holiday rental in Gloucester

Coastal retreat steps to the beach with smart TVs, desk, grill, children's items

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!, holiday rental in Gloucester
Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!, holiday rental in Gloucester
Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!, holiday rental in Gloucester

Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beach Life Bliss - steps to the beach, holiday rental in Gloucester
Beach Life Bliss - steps to the beach, holiday rental in Gloucester
Beach Life Bliss - steps to the beach, holiday rental in Gloucester

Beach Life Bliss - steps to the beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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#Weddings #Holidays #Corporate short term? Just need some “in between” place ?, holiday rental in Gloucester
#Weddings #Holidays #Corporate short term? Just need some “in between” place ?, holiday rental in Gloucester
#Weddings #Holidays #Corporate short term? Just need some “in between” place ?, holiday rental in Gloucester

#Weddings #Holidays #Corporate short term? Just need some “in between” place ?

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Romantic Summerwind Cottage,  Scenic Harbor View w/Deck!, holiday rental in Gloucester
Romantic Summerwind Cottage,  Scenic Harbor View w/Deck!, holiday rental in Gloucester
Romantic Summerwind Cottage,  Scenic Harbor View w/Deck!, holiday rental in Gloucester

Romantic Summerwind Cottage, Scenic Harbor View w/Deck!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean front and 3 beaches across ,parks, short walk to historic downtown!, holiday rental in Gloucester
Ocean front and 3 beaches across ,parks, short walk to historic downtown!, holiday rental in Gloucester
Ocean front and 3 beaches across ,parks, short walk to historic downtown!, holiday rental in Gloucester

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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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 6
Match: Sleeps
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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
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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
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Open concept, 2-level apartment with scenic view, holiday rental in Gloucester
Open concept, 2-level apartment with scenic view, holiday rental in Gloucester
Open concept, 2-level apartment with scenic view, holiday rental in Gloucester

Open concept, 2-level apartment with scenic view

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mill Pond Cottage: Historic Gloucester charm with modern comforts., holiday rental in Gloucester
Mill Pond Cottage: Historic Gloucester charm with modern comforts., holiday rental in Gloucester
Mill Pond Cottage: Historic Gloucester charm with modern comforts., holiday rental in Gloucester

Mill Pond Cottage: Historic Gloucester charm with modern comforts.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Good Harbor Beach Apt.- 6/10 mile, holiday rental in Gloucester
Good Harbor Beach Apt.- 6/10 mile, holiday rental in Gloucester
Good Harbor Beach Apt.- 6/10 mile, holiday rental in Gloucester

Good Harbor Beach Apt.- 6/10 mile

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy summer house near the beach, holiday rental in Gloucester
Cozy summer house near the beach, holiday rental in Gloucester
Cozy summer house near the beach, holiday rental in Gloucester

Cozy summer house near the beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Ocean Breeze / 8-Minute Walk to Beach, holiday rental in Gloucester
Ocean Breeze / 8-Minute Walk to Beach, holiday rental in Gloucester
Ocean Breeze / 8-Minute Walk to Beach, holiday rental in Gloucester

Ocean Breeze / 8-Minute Walk to Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Location location…min from Good Harbor Beach, holiday rental in Gloucester
Location location…min from Good Harbor Beach, holiday rental in Gloucester
Location location…min from Good Harbor Beach, holiday rental in Gloucester

Location location…min from Good Harbor Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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
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Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach., holiday rental in Gloucester
Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach., holiday rental in Gloucester
Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach., holiday rental in Gloucester

Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Glorious Suite near Downtown with washer/dryer, holiday rental in Gloucester
Glorious Suite near Downtown with washer/dryer, holiday rental in Gloucester
Glorious Suite near Downtown with washer/dryer, holiday rental in Gloucester

Glorious Suite near Downtown with washer/dryer

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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A walk up to heaven!, holiday rental in Gloucester
A walk up to heaven!, holiday rental in Gloucester
A walk up to heaven!, holiday rental in Gloucester

A walk up to heaven!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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River's Edge: A charming 2BR riverfront home in Gloucester., holiday rental in Gloucester
River's Edge: A charming 2BR riverfront home in Gloucester., holiday rental in Gloucester
River's Edge: A charming 2BR riverfront home in Gloucester., holiday rental in Gloucester

River's Edge: A charming 2BR riverfront home in Gloucester.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cape Ann Reset, holiday rental in Gloucester
Cape Ann Reset, holiday rental in Gloucester
Cape Ann Reset, holiday rental in Gloucester

Cape Ann Reset

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW Oceanside Village Home~Private Fenced Yard~Reserved Parking, holiday rental in Gloucester
NEW Oceanside Village Home~Private Fenced Yard~Reserved Parking, holiday rental in Gloucester
NEW Oceanside Village Home~Private Fenced Yard~Reserved Parking, holiday rental in Gloucester

NEW Oceanside Village Home~Private Fenced Yard~Reserved Parking

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Bayview Guest Cottage, holiday rental in Gloucester
Bayview Guest Cottage, holiday rental in Gloucester
Bayview Guest Cottage, holiday rental in Gloucester

Bayview Guest Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Quaint Home, Near Good Harbor Beach and Town, Great for Families, holiday rental in Gloucester
Quaint Home, Near Good Harbor Beach and Town, Great for Families, holiday rental in Gloucester
Quaint Home, Near Good Harbor Beach and Town, Great for Families, holiday rental in Gloucester

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Harbortown Hideaway: Charming home in downtown Gloucester with water views., holiday rental in Gloucester
Harbortown Hideaway: Charming home in downtown Gloucester with water views., holiday rental in Gloucester
Harbortown Hideaway: Charming home in downtown Gloucester with water views., holiday rental in Gloucester

Harbortown Hideaway: Charming home in downtown Gloucester with water views.

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!, holiday rental in Gloucester
Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!, holiday rental in Gloucester
Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!, holiday rental in Gloucester

Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck., holiday rental in Gloucester
Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck., holiday rental in Gloucester
Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck., holiday rental in Gloucester

Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Salt Island Views: Walking distance to Good Harbor & Long Beach., holiday rental in Gloucester
Salt Island Views: Walking distance to Good Harbor & Long Beach., holiday rental in Gloucester
Salt Island Views: Walking distance to Good Harbor & Long Beach., holiday rental in Gloucester

Salt Island Views: Walking distance to Good Harbor & Long Beach.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes, holiday rental in Gloucester
Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes, holiday rental in Gloucester
Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes, holiday rental in Gloucester

Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Harbor View Walk to Beach 3b2bKings4beds, holiday rental in Gloucester
Beautiful Harbor View Walk to Beach 3b2bKings4beds, holiday rental in Gloucester
Beautiful Harbor View Walk to Beach 3b2bKings4beds, holiday rental in Gloucester

Beautiful Harbor View Walk to Beach 3b2bKings4beds

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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Amazing Waterfront/Access 4BDRM in Riggs Point, holiday rental in Gloucester
Amazing Waterfront/Access 4BDRM in Riggs Point, holiday rental in Gloucester
Amazing Waterfront/Access 4BDRM in Riggs Point, holiday rental in Gloucester

Amazing Waterfront/Access 4BDRM in Riggs Point

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
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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~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer, holiday rental in Gloucester
~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer, holiday rental in Gloucester
~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer, holiday rental in Gloucester

~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sand Song: Just one block from Good Harbor Beach!, holiday rental in Gloucester
Sand Song: Just one block from Good Harbor Beach!, holiday rental in Gloucester
Sand Song: Just one block from Good Harbor Beach!, holiday rental in Gloucester

Sand Song: Just one block from Good Harbor Beach!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Perrywinkle: Waterfront on Gloucester’s Rocky Neck., holiday rental in Gloucester
Perrywinkle: Waterfront on Gloucester’s Rocky Neck., holiday rental in Gloucester
Perrywinkle: Waterfront on Gloucester’s Rocky Neck., holiday rental in Gloucester

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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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Elegant Gloucester Beach Getaway with Ocean Views!, holiday rental in Gloucester
Elegant Gloucester Beach Getaway with Ocean Views!, holiday rental in Gloucester
Elegant Gloucester Beach Getaway with Ocean Views!, holiday rental in Gloucester

Elegant Gloucester Beach Getaway with Ocean Views!

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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BEACH!  Good Harbor NEW CONSTRUCTION!!!!, holiday rental in Gloucester
BEACH!  Good Harbor NEW CONSTRUCTION!!!!, holiday rental in Gloucester
BEACH!  Good Harbor NEW CONSTRUCTION!!!!, holiday rental in Gloucester

BEACH! Good Harbor NEW CONSTRUCTION!!!!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Privacy and  a water view, five minutes  to a private beach., holiday rental in Gloucester
Privacy and  a water view, five minutes  to a private beach., holiday rental in Gloucester
Privacy and  a water view, five minutes  to a private beach., holiday rental in Gloucester

Privacy and a water view, five minutes to a private beach.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!, holiday rental in Gloucester
Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!, holiday rental in Gloucester
Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!, holiday rental in Gloucester

Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

Holiday Rental House
4 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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Seaside House: Good Harbor Beach and the Back Shore right outside your door., holiday rental in Gloucester
Seaside House: Good Harbor Beach and the Back Shore right outside your door., holiday rental in Gloucester
Seaside House: Good Harbor Beach and the Back Shore right outside your door., holiday rental in Gloucester

Seaside House: Good Harbor Beach and the Back Shore right outside your door.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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