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$220

3 BR / 2 BA / Sleeps 6

Captains Watch: 1 block to waterfront Boulevard & downtown.  3 beds/1.5 baths - Gloucester vacation rentals
1 / 21

$220

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Captains Watch: 1 block to waterfront Boulevard & downtown. 3 beds/1.5 baths

Gloucester house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Located just a lane away from Gloucester's iconic Stacey Boulevard, this 3 bedroom/1.5 bath gem is steps away from the harbor, two beaches, glorious Stage Fort Park and the vibrant downtown with a huge array of restaurants, galleries, shops, museums and historic places of worship. Located on a tiny lane just off of …
  • Internet Access
  • Patio
  • Grill
  • Linens Provided
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$325

5 BR / 3 BA / Sleeps 12

2 Reviews

$325

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The Pratt House on the Boulevard

Gloucester house
5 BR / 3 BA / Sleeps 12 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Spacious 5 Bedroom Brick Colonial Home located on the Historic Stacey Boulevard with picturesque views of Gloucester's Harbor and the Atlantic Ocean. Look out at the stunning views of local schooners, the light houses, fishing vessels and feel the cool sea breeze that provides refreshment from the warm summer days. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(2)

Can't say enough about how wonderful Pratt House is!

Left on Aug 25, 2014 for a stay in August 2014

We had such a wonderful stay here! We came with our five kids, ages 11-24, for a last hurrah together before 2 of our older kids left home for college and living abroad. We were trying to figure out on the first night why we felt so "at home"--the girls pointed out that the house was so well furnished and had everything we needed; it didn't feel like a rental, it felt like a friend had lent us …

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$200

2 BR / 1 BA / Sleeps 5

10 Reviews

$200

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Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage
2 BR / 1 BA / Sleeps 5 | Quick view
Excellent10 Reviews

Details

Reviews

(10)

Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large private deck overlooking the harbor, separate dining…
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(10)

Perfect little getaway In Gloucester!

Left on Feb 07, 2012 for a stay in November 2011

I love, love, love this apartment! Spent a week there in the fall of 2011. The weather was perfect and I enjoyed many a sunset on the balcony with a great view of Gloucester Harbor.

The kitchen is modern and just right for one or two. We had everything we needed. Nicely decorated and well furnished, this is a great little hideaway. Easy to find, parking is right outside the door. The bed was …

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$220

3 BR / 1 BA / Sleeps 6

Annie's Place: Just 0.2 miles to beautiful Plum Cove Beach - Gloucester vacation rentals
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$220

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Annie's Place: Just 0.2 miles to beautiful Plum Cove Beach

Gloucester house
3 BR / 1 BA / Sleeps 6 | Quick view

Details

A delightful home situated in Gloucester's charming Bay View neighborhood, Annies Place radiates an aura of sun and warmth. Only an 8 minute walk to lovely Plum Cove Beach, Annies Place lets you spend your summer vacation relaxing, discovering local fauna such as hermit crabs, and swimming to your hearts content! In …
  • Internet Access
  • Porch
  • Grill
  • Linens Provided
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

4 BR / 2 BA / Sleeps 12

10 Reviews

$215

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Vacation Home/Spectacular Ocean Views and Sunsets

Gloucester house
4 BR / 2 BA / Sleeps 12 | Quick view
Excellent10 Reviews

Details

Reviews

(10)

This oceanfront year round home was recently constructed to maximize spectacular ocean views and sunsets. Enjoy the views of the water outside while sitting on the glassed in balcony just off of the master bedrooms , the screen/glass windows across the front or on the stone patio or dock. Inside, there is an expanse …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(10)

Relaxation and Wonderful Seascapes

Left on Jul 26, 2010 for a stay in August 2009

We came from Ireland to visit with the american branch of the family and this was an ideal location. The accommodation is spacious and bright with excellent bathroom facilities, comfortable bedrooms and lots of living space for either socialising or spending quiet time -reading - lots of books provided - or chilling out on the private dock. The bedroom balcony area is terrific for a quiet cup …

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$500

5 BR / 3 BA / Sleeps 11

Dragonfly - Gloucester vacation rentals
1 / 13

$500

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Dragonfly

Gloucester house
5 BR / 3 BA / Sleeps 11 | Quick view

Details

Turn of the century home located two blocks from Atlantic shoreline and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat. Large modern fully equipped kitchen with double oven, 6 burner stove, dishwasher, washer, dryer. Three fireplaces, large garden area, …
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area

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$314

4 BR / 1 BA / Sleeps 6

1 / 6

$314

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Ocean Front Cottage

Gloucester cottage
4 BR / 1 BA / Sleeps 6 | Quick view

Details

Updated seasonal waterfront cottage ideal for swimming or kayaking right from the property. It is located on the Northeast shore of Cape Ann, affording sweeping views of Ipswich Bay, with gorgeous summer sunsets over the water. It is nestled in among three other waterfornt cottages in a quiet oceanfront residential …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$390

3 BR / 2 BA / Sleeps 8

1 / 21

$390

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Good Harbor Beach Escape: AC, Gas Fireplace & Walk to Beach

Gloucester house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

Walk to Gloucester's best beach - Good Harbor, located just 0.2 miles from this wonderful duplex, which offers three air conditioned bedrooms and two full custom tile baths with showers. Enter into the open concept living, dining and kitchen areas complete with parquet floors, which make the ideal setting for …
  • Internet Access
  • Fireplace
  • Patio
  • Books
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$429

5 BR / 2 BA / Sleeps 13

1 / 19

$429

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Beachside at Good Harbor

Gloucester house
5 BR / 2 BA / Sleeps 13 | Quick view

Details

**There is a possibility that construction will ongoing next door during the summer of 2015** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two separate living spaces as well as two full kitchens and a…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Balcony or terrace
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$150

1 BR / 1 BA / Sleeps 2

1 / 5

$150

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"Le Beauport", Gloucester, Ma.

Gloucester condo
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Sitting directly on the the beautiful port of Gloucester Harbor, this light and airy 3 room apartment offers full private bath, fully applianced kitchen, queen bed and wonderful sitting porch. Walk or bike to local restaurants, museums, theatre and beach, and enjoy all that is Gloucester. The trolly and MBTA train …
  • Waterfront
  • Ocean or water views
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$350

3 BR / 2 BA / Sleeps 8

1 / 23

$350

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Harbor Watch: 3 br gem right on Stacey Boulevard

Gloucester condo
3 BR / 2 BA / Sleeps 8 | Quick view

Details

This well appointed 3 bedroom/ 2 bath pied a'terre is perched above the picturesque waterfront Stacey Boulevard which is one of the most scenic spots on all of Cape Ann- best known for the iconic Man-at-the-Wheel sculpture of the Gloucester Fisherman facing the elements of the sea depicting "Those that go down to the …
  • Ocean or water views
  • Internet Access
  • Books
  • Linens Provided
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$210

2 BR / 1 BA / Sleeps 4

1 / 12

$210

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Garden by the Sea: Relax and enjoy the wonderful coastal views in Gloucester!

Gloucester condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom apartment. Both the living room and the master bedroom have sliding doors that open onto a spacious, private, sun-kissed deck complete with gorgeous water …
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$279

3 BR / 1 BA / Sleeps 6

1 / 9

$279

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Beautiful Bayshore Cottage

Gloucester cottage
3 BR / 1 BA / Sleeps 6 | Quick view

Details

The cottage is an updating of the original Coggeshall artist camp overlooking a grassy acre of land leading to its own point of land jutting into Ipswich Bay. With prevailing calm water the shorefront is usable for swimming and boating (boat launch 1/2 mile at Lane's Cove). The cottage is at the end of the built-up …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$285

4 BR / 2 BA / Sleeps 7

1 Reviews

$285

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Annisquam's Buoy 23: 4BR Waterfront w/Dock

Gloucester house
4 BR / 2 BA / Sleeps 7 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

NEW IN 2013: Addition of new windows, insulation, Heat & Central Air Conditioning now extends our season March 1 – December 31.This newly renovated and updated waterfront gem has four bedrooms and 1.5 baths, a deep-water dock (accommodates up to a 20 foot boat) and a wrap-around screened porch where one can sit and …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

This is the place to relax with or without family

Left on Feb 03, 2015 for a stay in June 2014

We try to stay here every year because we love the comfortable quality of a vacation home that's been in the family since 1929. The roomy screened in porch wraps around 3 sides of this comfy cottage overlooking the Anisquam and the changing tides and boats going by make for constant entertainment. The Kingsleys stock everything you might need and the furniture is all sturdy and comfortable…

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$125

4 BR / 8 BA / Sleeps 8

4 Reviews

$125

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"Misselthwaite Manor" By The Sea, Eastern Point

Gloucester house
4 BR / 8 BA / Sleeps 8 | Quick view
Very Good4 Reviews

Details

Reviews

(4)

English Manor Home reminiscent of the Cottswolds, "Misselthwaite Manor" is a a quiet respite in a busy world, yet in the middle of everything Historic Gloucester has to offer. Currently booking for July and August at special rates for two week blocks. Located in the heart of the private peninsula of Eastern Point, …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

A wonderful place to stay!!!

Left on May 10, 2014 for a stay in May 2014

My wife and I spent the weekend of May 2-3, 2014 at the Misselthwaite Manor. We had a wonderful time!! The room was quite big and very comfortable. The king size bed was great to sleep on. The house was very quiet. Lois, the owner, was very easy to deal with. She was friendly and helpful. She made me very comfortable within minutes of entering the manor. Lois provided good breakfasts on both …

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$322

2 BR / 2 BA / Sleeps 4

1 / 18

$322

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Waterfront Vacation House w/ Dock

Gloucester house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So surrounded by water, it feels…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children

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$12

1 BR / 1 BA / Sleeps 2

1 / 4

$12

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Test Property- TA Test

Gloucester cottage
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Title Travelers see this first while they are browsing properties, so be sure your title stands out. Description Give travelers an idea of what to expect from a stay in your rental. What is the space like? What's nearby? What makes it special? Give travelers an idea of what to expect from a stay in your rental. What …
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$336

3 BR / 1 BA / Sleeps 6

1 / 43

$336

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Amazing View Hilltop Cottage Private Beach

Gloucester cottage
3 BR / 1 BA / Sleeps 6 | Quick view

Details

Lovely cottage set high up on a hill overlooking the private section of Wingaersheek Beach, this lovingly restored 3 bedroom home has been in the same family for over 55 years. The cottage boasts one of the most spectacular hilltop views on the entire beach with meticulously maintained lawn and gardens. The layout is …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

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$175

2 BR / 1 BA / Sleeps 4

1 / 16

$175

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Waterfront Harbor Summer weeks still available

Gloucester condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around harbor by boat is all within reach. Purchase …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

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$235

2 BR / 2 BA / Sleeps 4

1 / 27

$235

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Treehouse - 2 beds/ 1.5 baths and walk to town and beach

Gloucester house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacey Boulevard is home to the iconic "Gloucester Fisherman at the Wheel" sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets, painters, and movie …
  • Ocean or water views
  • Internet Access
  • Deck
  • Books
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,050

4 BR / 3 BA / Sleeps 8

1 / 50

$1,050

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Cool Cove: Wingaersheek Beach plus your own private beach & all those views!

Gloucester house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Sun when you want it. Shade when you need it. Cool Cove has it all. Jutting high above Wingaersheek Beach on a promontory from which it seems that you can see forever: Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, Walk from this four bedroom house, across a verdant lawn edged with Rosa Rugosa …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,714

5 BR / 3 BA / Sleeps 12

1 / 51

$1,714

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PRIVATE SPECTACULAR WINGAERSHEEK OCEANFRONT ESTATE

Gloucester house
5 BR / 3 BA / Sleeps 12 | Quick view

Details

LUXURY OCEANFRONT ESTATE CLOSE TO BOSTON This truly unique, breathtaking oceanfront circa 1890 estate has been painstakingly renovated and modernized by its current owner. The property consist of close to 4 acres of direct oceanfront access with a 4,000 sf stone house that boasts an attached first and second …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$90

1 BR / 1 BA / Sleeps 2

1 Reviews

$90

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Adorable One Bedrm Cottage in East Gloucester

Gloucester cottage
1 BR / 1 BA / Sleeps 2 | Quick view
Very Good1 Reviews

Details

Reviews

(1)

Enjoy all that Gloucester has to offer in this charming 1BD cottage by the harbor in East Gloucester. Located on main street so busy during the day, but close to everything by foot or bicycle. Sunny, furnished, adorable 1BD. Living Room/Kitchenette downstairs, Bedroom/Bath upstairs. Nestled among yacht yards, …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask

Details

Reviews

(1)

Quaint, clean cottage in convenient area.

Left on Aug 15, 2014 for a stay in July 2014

Recommend it to couples only, quaint, very clean cottage in a busy area. Take caution pulling out of driveway. Bathroom upstairs a little small not much head room for those over 5'8". Enjoyed our stay, the owners very nice and helpful.

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$380

3 BR / 3 BA / Sleeps 8

1 / 32

$380

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Water's Edge: Direct waterfront on picturesque Goose Cove

Gloucester house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

Direct waterfront on picturesque Goose Cove, this immaculate property provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and living areas and a big …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Clothes Dryer
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$420

5 BR / 2 BA / Sleeps 9

1 / 36

$420

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Beachmont: 0.2 miles from Cressy Beach

Gloucester house
5 BR / 2 BA / Sleeps 9 | Quick view

Details

Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian house has been in the same family since the 1880's. From the side entrance on a quiet lane, you will step into a bright back hall with full bath and separate laundry…
  • Internet Access
  • Fireplace
  • Porch
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,100

5 BR / 3 BA / Sleeps 9

1 / 29

$1,100

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Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach

Gloucester house
5 BR / 3 BA / Sleeps 9 | Quick view

Details

DIRECT WATERFRONT on Good Harbor Beach, Gloucester's finest stretch of sand, is literally steps away from this gracious and beloved, family friendly five bedroom summer cottage on picturesque Brier Neck. Sit on the waterfront terrace/patio and enjoy the summer breezes and unobstructed views of the glittering tides …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Fireplace
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$200

2 BR / 2 BA / Sleeps 6

1 / 17

$200

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Water's Edge Too: Direct waterfront on the banks of picturesque Goose Cove

Gloucester cottage
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Featuring a waterfront location, 2 bedrooms, 2 baths, and the option to rent the adjacent 3 bedroom, 3 bath home, Water’s Edge Too makes for the perfect family getaway. (If you have a large number in your party, you should note that both homes combined can easily sleep a total of 14 individuals.) As you sit out on …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Porch
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$780

6 BR / 6 BA / Sleeps 16

1 / 44

$780

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Bell View: Plenty of room for everyone

Gloucester house
6 BR / 6 BA / Sleeps 16 | Quick view

Details

This spacious and gracious center stair colonial offers incredible versatility to suit your specific vacation needs. The house can accommodate just your family of 5 or your extended family of up to 16+ depending upon the make up of your group, making it the perfect getaway for smaller or larger groups as their home …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

2 BR / 1 BA / Sleeps 3

1 / 12

$150

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Griffin's Getaway: Sweet 2 bedroom apartment with views of Ipswich Bay!

Gloucester condo
2 BR / 1 BA / Sleeps 3 | Quick view

Details

This sweet two bedroom apartment has views of Ipswich Bay from its second floor vantage point. It has an open plan living/dining room/kitchen and spacious tiled bathroom. One bedroom has a queen bed and a single; the second bedroom has a single. There is a large fenced-in yard for your use and parking for two cars at …
  • Ocean or water views
  • Internet Access
  • Grill
  • Linens Provided
  • Freezer
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,572

3 BR / 4 BA / Sleeps 6

1 / 35

$1,572

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Rosemarc House: Private beach, 180-degree views & a baby grand piano.

Gloucester house
3 BR / 4 BA / Sleeps 6 | Quick view

Details

This is one of the few properties that has stairs that take you directly onto the private portion of Good Harbor Beach. This immaculate 3 bedroom, 3.5 bath contemporary home is the ultimate beach getaway. Incredible 180 degree views of the whole length of the beach, Salt Island and north up the coast, the inside of …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$650

3 BR / 3 BA / Sleeps 10

1 / 31

$650

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Long Beach Condo -Steps from the white sand and surf, sleeps 10+,central A/C

Gloucester condo
3 BR / 3 BA / Sleeps 10 | Quick view

Details

Just 10 yards from the white sands and lively surf of Long Beach, this condo sleeps 10+ in centrally air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named beach is one mile long spanning both the community of Gloucester and Rockport - take your pick! This unit has …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

1 BR / 1 BA / Sleeps 3

1 / 16

$198

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Beach Walk: Good Harbor Beach footbridge just steps away!

Gloucester condo
1 BR / 1 BA / Sleeps 3 | Quick view

Details

Good Harbor Beach! Friday to Friday rental! Step out the door, walk over the Good Harbor Beach footbridge and you are on one of Gloucester’s most highly rated beaches enjoying the sun, sand, and surf. Leave your car in the driveway and enjoy the best of summer; run home for refreshments & come back to the beach. …
  • Ocean or water views
  • Internet Access
  • Patio
  • Books
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$943

3 BR / 5 BA / Sleeps 8

1 / 35

$943

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Ocean Whisper House: Water views abound from this amazing 3+ bed/4.5 bath.

Gloucester house
3 BR / 5 BA / Sleeps 8 | Quick view

Details

RENTING FOR AUGUST 2015. Ocean Whisper House is the high end, waterfront, air conditioned home you have been waiting for. The house has everything you could wish for with 3 ensuite bedrooms and 4.5 baths, AND it comes with a parking pass to park on Beach Street at Good Harbor Beach. Or if you like a smaller, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$500

2 BR / 3 BA / Sleeps 4

1 / 46

$500

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Paradise Point: Direct Waterfront with deepwater dock & sunsets

Gloucester house
2 BR / 3 BA / Sleeps 4 | Quick view

Details

Direct waterfront with a deep water dock perfect for boating, swimming or just relaxing while waving to the passing boats or drinking in the glorious sunsets. Two bedrooms and 2.5 bath home perched at the edge of the sparkling waters of the tidal Annisquam River, the house is great for entertaining and enjoying the …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$300

3 BR / 2 BA / Sleeps 8

1 / 15

$300

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Lighthouse Way: Walk 0.2 miles to the beach from this cozy, renovated home!

Gloucester house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

This completely renovated 3 bedroom, 1.5 bath is a tastefully and comfortably decorated family home that is on a quiet dead end street which is about 100 yards from the sands of Niles Beach. A short walk to the Art colony of Rocky Neck with its galleries and restaurants, you will have plenty to keep you busy, if you …
  • Internet Access
  • Porch
  • Grill
  • Linens Provided
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$440

4 BR / 3 BA / Sleeps 8

1 / 37

$440

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Sea Fox: Walk to private Coffins Beach

Gloucester house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

This bright and open contemporary home was custom designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all is kept cool with central air conditioning. Enjoy your access …
  • Private Beach
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Books
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$400

3 BR / 4 BA / Sleeps 7

1 / 12

$400

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River Breezes: Direct Waterfront with sunsets!

Gloucester cottage
3 BR / 4 BA / Sleeps 7 | Quick view

Details

Enjoy the views of the sparkling waters of the Annisquam River and Ipswich Bay beyond as well as Wingarsheek Beach and the Annisqaum Yacht Club just across the river. Don't forget the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath gem which efficiently and effectively packs a surprising …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Porch
  • Books
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$400

4 BR / 2 BA / Sleeps 8

1 / 17

$400

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Skippers Sunset House: Vista views & easy walk to Coffins Beach

Gloucester house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

Just 2/10 of a mile from the white sands and surf of Coffins Beach making this immaculate 4 bedroom/2 bath home the perfect beach getaway for you. The house is perched above it all with vista views of the ocean, beach, neighboring pond and surrounding hills and you can enjoy these views from just about any window in …
  • Ocean or water views
  • Internet Access
  • Deck
  • Books
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$134

1 BR / 1 BA / Sleeps 2

1 / 41

$134

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Art Haven: Direct waterfront with large deck and dock! One month minimum.

Gloucester condo
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Located in Gloucester’s Rocky Neck Cultural District, this charming one bedroom waterfront retreat is perfect for aspiring artists, photographers, or anybody who appreciates the captivating beauty of the ocean! Sit on the deck and breathe in the salty air as you overlook Smith Cove, or fish off the nearby dock as …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Deck
  • Books
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$786

4 BR / 3 BA / Sleeps 10

1 / 30

$786

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Seaside House: Walk 0.2 mi to Good Harbor Beach / Waterviews 4 beds 2.5 baths

Gloucester house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

Location, location, location! Waterviews & walk to Good Harbor Beach. This four bedroom/2.5 bath home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so close to Cape Ann's most popular beach and also has water views of …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Porch
  • Books
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$565

4 BR / 2 BA / Sleeps 10

1 / 31

$565

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Sand Song: Just 1 block to Good Harbor Beach

Gloucester house
4 BR / 2 BA / Sleeps 10 | Quick view

Details

This delightful and charming home is ideally situated just one block from Good Harbor Beach overlooking the sand and the surf. Four bedrooms and two full baths, the house is well laid out and has fantastic views of the beach. Enter into the center stair foyer and on your left is a large living room with a fireplace…
  • Ocean or water views
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$286

3 BR / 2 BA / Sleeps 6

1 / 23

$286

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Victorian House: Gorgeous home on Rocky Neck and just 0.2 miles to beach.

Gloucester house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Tastefully renovated, Victorian House on Rocky Neck, Gloucester’s fabled artist colony has three bedrooms and a gorgeous front porch overlooking the water. From the porch, step into the home’s front hall and formal living room, complete with a custom delicately-tiled fireplace. Open the nearby French doors to …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Patio
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$325

3 BR / 2 BA / Sleeps 6

1 / 9

$325

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East gloucester house amazing view!!!

Gloucester house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Awesome East Gloucester house with picture perfect view! Sip cocktails and watch the boats go by. Walk to Rocky Neck for great dining, art galleries, and more. Enjoy the music from the Neck while sitting on your own deck. A short walk to Niles Beach, bring your bikes or running shoes and run or bike the 5 mile famous …
  • Ocean or water views
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$93

4 BR / 2 BA / Sleeps 8

1 / 7

$93

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Gloucester - Good Harbor Beach View Home

Gloucester house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

One acre up on quiet bluff, with new view deck and windows overlooking the best beach north of Boston, is our four bedroom, two bath house with lots of parking and just 1500 yards from the ocean. Come and stay with your family or friends and enjoy Good Harbor Beach and all of historic and original Gloucester, Mass. …
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

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