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$656
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$160
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf
Gloucester house
- 2 bedrooms
- 1 bathroom
- sleeps 4
Responds fast! avg. 3 hours 2 minutes
Price per night from
$118
“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.
Price per night from
$322
Price per night from
$201
Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)
Gloucester house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
Price per night from
$1,033
Price per night from
$259
Long Beach and Good Harbor Beach summer rental - Gloucester, MA
Gloucester house
- 3 bedrooms
- 1 bathroom
- sleeps 6
Price per night from
$329
Price per night from
$402
Great rentals within 20 miles that match your search
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. 21 minutes
Price per night from
$167
Price per night from
$952
GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
Rockport apartment
- 2 bedrooms
- 1 bathroom
- sleeps 3
Responds fast! avg. 3 hours 17 minutes
Price per night from
$282
OCEAN VIEW COTTAGE AT THE SEAWARD - EASY SEASIDE PATH TO OLD GARDEN BEACH
Rockport cottage
- 2 bedrooms
- 1 bathroom
- sleeps 4
Responds fast! avg. 3 hours 17 minutes
Price per night from
$339
LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN
Rockport apartment
- 1 bedroom
- 1 bathroom
- sleeps 2
Responds fast! avg. 3 hours 17 minutes
Price per night from
$305
GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
Rockport cottage
- 2 bedrooms
- 1 bathroom
- sleeps 2
Responds fast! avg. 3 hours 17 minutes
Price per night from
$282
Price per night from
$197
Responds fast! avg. 3 hours 17 minutes
Price per night from
$350
Beach Front Luxe: Italian vibes & coastal glam in Rockport!
Rockport house
- 5 bedrooms
- 2 bathrooms
- sleeps 12
Responds fast! avg. 1 hour 32 minutes
Price per night from
$747
Price per night from
$192
Price per night from
$287
Price per night from
$29
Responds fast! avg. 3 hours 29 minutes
Price per night from
$689
Price per night from
$660
SEASIDE GARDENS AFFORDABLE GUEST ROOM(S) IN VILLAGE BY BEACH, WALK EVERYWHERE!
Rockport b&b
- 1 bedroom
- 1 bathroom
- sleeps 2
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
Price per night from
$184
Price per night from
$574
Price per night from
$517
Price per night from
$287
Price per night from
$919
Luxurious 3 Story Beachfront Home! Newly Furnished & Captivating Views!
Plum Island house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Price per night from
$660
Price per night from
$702
Price per night from
$190
Viewing 38 of 62
rentals in Gloucester
About Gloucester
Located on the northern shores of Massachusetts, the town of Gloucester is a vacation paradise that generations of travelers return to every year. The winding streets of this historic town are lined with quaint shops, interesting museums, charming cafes, and unforgettable seafood restaurants. Come here to experience the beautiful rocky coastlines and soft sand beaches of Massachusetts. Hike the trails and stop at breathtaking overlooks with views of the Atlantic Ocean. Visit historic homes and lighthouses. Spend the afternoon swimming, snorkeling, or relaxing on a pristine beach. And then go home at night to your own private vacation rental and host dinner for your family and friends. Many vacation rentals in Gloucester are less expensive than hotels and offer more space and better amenities. Wake up in the morning and watch the sun rise from the deck of your beach condo or summer house, then head downtown to spend the day exploring and making fun vacation memories.
Here are a few additional suggestions for your trip:
- Take a brewery tour: Gloucester is the traditional home of several long established breweries and craft distilleries. Taste some of the area's award winning artisanal spirits.
- Tour Hammond Castle: This extraordinary structure was once the home of John Hays Jr., a wealthy eccentric who amassed an extensive collection of medieval artifacts.
- Visit the Fisherman's Memorial Monument: This fascinating memorial was built in 1925 to honor all the fishermen who have been lost at sea since the 17th century.
- Play on the beach: Swim, build a sandcastle, or just relax on Good Harbor Beach or Stage Fort Park and Beach, two of the most popular beach destinations in the area.
- Visit the Rocky Neck Art Colony: This is the oldest established colony for artists in the United States and has been a destination for art lovers since the 1840s.
- Visit the Beauport Museum or the Cape Ann Historical Museum: Learn more about the fascinating history of Cape Ann with the changing exhibits of these popular museums.
Gloucester offers an ideal scenic back drop for whatever vacation activities you have in mind. The best way to enjoy it all is with a stay in your own apartment rental or summer condo. Find a luxury vacation rental just a few steps from the beach that offers all the amenities you and your family need. While you're visiting Gloucester, be sure to plan day trips to coastal destinations nearby like Cape Cod and Plymouth.
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