Vacation Rentals & Houses in Gloucester

Updating...

age 0-16
62 Results

Relevance

Price: low to high

Price: high to low

Reviews

62 houses

At the Footbridge entrance to Good Harbor Beach

Gloucester house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$655

Bohemia RETREAT Studio

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$258

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$160

Responds fast! avg. 1 hour 4 minutes

Price per night from

$118

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.

Price per night from

$316

Test Property- TA Test

Gloucester cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$14

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

Gloucester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,032

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

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$328

Waterfront Woodsy 3BR Cottage

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$401

Responds fast! avg. 1 hour 4 minutes

Price per night from

$118

Great rentals within 20 miles that match your search

Back Beach

Rockport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$492

BEACHFRONT - Directly on Long Beach Rockport MA

Rockport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 28 minutes

Price per night from

$688

Large Furnished room for rent, quiet location

Lynn apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

Price per night from

$29

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Price per night from

$281

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

Price per night from

$338

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

Rockport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$304

Beach & King Street Inn / Beach House Rental

Rockport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$950

“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

Price per night from

$167

Gap Cove at The Seaward

Rockport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$350

The Little Red House with Prize Ocean View

Rockport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$196

Oceanfront Penthouse at Salisbury Beach

Salisbury condo

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$573

Cozy bedroom apartment in a heart of

Beverly apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$192

Downtown Beverly's hidden gem

Beverly house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$189

Beach Front Luxe: Italian vibes & coastal glam in Rockport!

Rockport house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 44 minutes

Price per night from

$745

ROCKPORT MA OLD GARDEN BEACH RENTAL !

Rockport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$459

Big New England Family Home; walk to beach, shops

Rockport house

  • 9 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$1,032

Sunshine House steps from Beach

Seabrook house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$802

Price per night from

$161

Luxurious 3 Story Beachfront Home! Newly Furnished & Captivating Views!

Plum Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$659

Crow Haven Corner Presents Lorelei's Witch House

Salem house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$659

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$189

Exclusive Lifestyle near the Ocean

Marblehead house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$917

Salisbury Coastal Retreat

Salisbury studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$195

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

Salem apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$287

Modern Oceanfront Home Swampscott

Swampscott house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Price per night from

$700

Price per night from

$184

The Harborfront, Beverly/Salem, Boston North Shore

Beverly apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$516

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.

Top Destination reviews

Romantic SUMMERWIND COTTAGE- Scenic Harbor View
Romantic Summerwind Cottage lives up to its name

We thoroughly enjoyed our stay in "Summerwind". It is a truly beautiful house. Linda and Hank, you did a wonderful job in remodeling and decorating the place. The color scheme and artwork reflect the lovely area and the lifestyle of Gloucester and we truly enjoyed the ambiance here. We felt very comfortable and welcomed in the house which was spotlessly clean and furnished with everything one could possibly need for their stay. We loved the area of East Gloucester. Good Harbor beach was a very enjoyable walk from the house. Rocky Neck and the Eastern Point Lighthouse were also very near and Rockport is only a short drive away. Our favorite restaurants were "My place by the Sea" in Rockport, "7th Wave " also in Rockport and "The Rudder" in Rocky Neck. We also enjoyed the beer at the Cape ann Brewing Company in Gloucester. And best of all was a barbecue on our veranda overlooking the Gloucester harbor. This was also where we enjoyed breakfast each morning watching the activity below. Linda, your exceptional taste and attention to detail made us choose Summerwind Cottage and we were not disappointed - it surpassed our expectations. A big thank you from Mira, Dominic and family (Ireland).see more

Also consider