Houses & Vacation Rentals in Gloucester

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Parking
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Beach or lakeside relaxation
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37 houses

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At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$654

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$160

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

2 bedrooms
1 bathroom

sleeps 4

“Gorgeous in every way” The cottage is tasteful, beautiful, comfortable and convenient. The views of the wonderful working harbor are breathtaking. The sunsets, seen from the deck while relaxing, dining, drinking coffee or something else are singularly spectacular. The color scheme in the cottage, the attention to detail, the artwork - all conspire to make the entire experience of being there as relaxing and enjoyable as it could possibly be. I would recommend Summerwind Cottage to anyone. I hope to return regularly. On top of all its other charms, the owners-Hank and Linda-are delightful people that I would love to see again under any circumstances.

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Price per night from

$344

Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)

Gloucester house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$1,031

Long Beach and Good Harbor Beach summer rental - Gloucester, MA

Gloucester house

3 bedrooms
1 bathroom

sleeps 6

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Price per night from

$328

Waterfront Woodsy 3BR Cottage

Gloucester house

3 bedrooms
1 bathroom

sleeps 6

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Price per night from

$401

Great rentals within 20 miles that match your search

Big New England Family Home; walk to beach, shops

Rockport house

9 bedrooms
4 bathrooms

sleeps 14

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Price per night from

$1,030

Salisbury Coastal Retreat

Salisbury studio

Studio
1 bathroom

sleeps 2

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Price per night from

$195

Sunshine House steps from Beach

Seabrook house

4 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$800

NEW! Family-Friendly Getaway < 1 Mi to Dtwn Salem!

Salem apartment

3 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$686

BEACHFRONT - Directly on Long Beach Rockport MA

Rockport house

4 bedrooms
3 bathrooms

sleeps 14

Responds fast! avg. 3 hours 44 minutes

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Price per night from

$687

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

2 bedrooms
1 bathroom

sleeps 2

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Price per night from

$281

OCEAN VIEW COTTAGE AT THE SEAWARD - EASY SEASIDE PATH TO OLD GARDEN BEACH

Rockport cottage

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$338

GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN

Rockport apartment

2 bedrooms
1 bathroom

sleeps 3

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Price per night from

$281

LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN

Rockport apartment

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$304

Beach & King / Beach House - 10% off April & May, 2024!

Rockport house

6 bedrooms
5 bathrooms

sleeps 12

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Price per night from

$974

SEASIDE GARDENS AFFORDABLE GUEST ROOM(S) IN VILLAGE BY BEACH, WALK EVERYWHERE!

Rockport b&b

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$161

Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING

Rockport b&b

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$184

Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet

Rockport cottage

1 bedroom
1 bathroom

sleeps 2

“An Oasis By The Sea” August 30, 2012 Dear Rose & Guy- Thank you very, very much for our wonderful stay at Periwinkle Cottage! From the beautifully decorated rooms, the most comfortable beds, soft luxurious towels and linens, convenient kitchen, TV to the lovely outdoor sitting area and garden... Omg...what a gem! It is a true delight! And the cottage is immaculate and very peaceful and tranquil. We will definitely recommend your "oasis by the sea" to our family and friends! Love, Penny and Urs Westport, Connecticut

Responds fast! avg. 2 hours 13 minutes

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Price per night from

$166