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Gloucester Massachusetts Vacation Rentals - Home
1 / 52

Gloucester Home
4 Bedrooms / 1.5 Bathrooms / Sleeps 7
Home / 4 Bedrooms / Sleeps 7

(3)“ Excellent ”3 Reviews

from

$285

/ night

Email Owner
Bedrooms:4
Bathrooms:1.5
Sleeps:7
Type:Home
Per night:$285 - $428
Per week:$1,995 - $2,995
Pets allowed:Yes
Internet:Yes

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-...

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Richard July 2014 vacation

“ Excellent ”
July 27, 2014
Staying at Buoy 23 is awesome. All you need to bring is you and your bathing suit everything else is provided down to a bar of soap. The kitchen itself has everything you could ask for. Linens and towels are provided as well. The only thing I could think of to make it that much better is maybe having something out side to store the cushions in for the out door chairs but other than that it was a fabulous vacation. Thank you for the use of your home Scott.
Lisa Richard, South Windsor, CT

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Cottage from the shore
1 / 6

Gloucester Cottage
4 Bedrooms / 1 Bathroom / Sleeps 6
Cottage / 4 Bedrooms / Sleeps 6

from

$315

/ night

Email Owner
Bedrooms:4
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$315
Per week:$2,200
Pets allowed:No
Internet:Yes

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...

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Front of Tuppeny Tower
1 / 51

Gloucester Home
5 Bedrooms / 3 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

Bedrooms:5
Bathrooms:3
Sleeps:12
Type:Home
Per night:$1,715 - $2,429
Per week:$12,000 - $17,000
Pets allowed:No
Internet:Yes

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 ...

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Gloucester Massachusetts Vacation Rentals - Cottage
1 / 9

Gloucester Cottage
3 Bedrooms / 1 Bathroom / Sleeps 6
Cottage / 3 Bedrooms / Sleeps 6

from

$279

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$279
Per week:$1,950
Pets allowed:No
Internet:Yes

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...

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aerial view
1 / 44

Gloucester Home
6 Bedrooms / 6 Bathrooms / Sleeps 16
Home / 6 Bedrooms / Sleeps 16

from

$825

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:16
Type:Home
Per night:$825 - $1,100
Per week:$4,125 - $5,658
Pets allowed:No
Internet:Yes

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...

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View of Good Harbor Beach from the house.
1 / 29

Gloucester Home
4 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$500

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$500 - $584
Per week:$3,500 - $4,088
Pets allowed:No
Internet:Yes

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 ...

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Aerial View of house with Good Harbor Beach in the upper right
1 / 32

Gloucester Home
4 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$735

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$735
Per week:$5,142
Pets allowed:No
Internet:Yes

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...

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1 / 29

Gloucester Home
5 Bedrooms / 3 Bathrooms / Sleeps 9
Home / 5 Bedrooms / Sleeps 9

Bedrooms:5
Bathrooms:3
Sleeps:9
Type:Home
Per night:$1,100 - $1,400
Per week:$5,150 - $6,900
Pets allowed:No
Internet:Yes

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...

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Lighthouse Way exterior.
1 / 20

Gloucester Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$294

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$294
Per week:$2,058
Pets allowed:Yes
Internet:Yes

This 3 bedroom, 1. 5 bath home on a quiet Gloucester cul de sac is about 100 yards from the sands of Niles Beach and just a short walk to the f Rocky Neck Art Colony with its galleries and restaurants. The Gloucester Stage Company is also in the neighborhood offering a top rated ...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 37

Gloucester Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$450

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$450 - $715
Per week:$2,325 - $3,232
Pets allowed:No
Internet:Yes

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...

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View from Master Bedroom porch
1 / 35

Gloucester Home
3 Bedrooms / 5 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

Bedrooms:3
Bathrooms:5
Sleeps:8
Type:Home
Per night:$1,200
Per month:$36,000
Pets allowed:No
Internet:Yes

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 ...

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Gloucester Massachusetts Vacation Rentals - Cottage
1 / 19

Gloucester Cottage
3 Bedrooms / 4 Bathrooms / Sleeps 7
Cottage / 3 Bedrooms / Sleeps 7

from

$450

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:7
Type:Cottage
Per night:$450 - $660
Per week:$2,100 - $2,920
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Cottage
1 / 17

Gloucester Cottage
2 Bedrooms / 2 Bathrooms / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

from

$303

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$303
Per week:$1,407
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 43

Gloucester Home
3 Bedrooms / 4 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$1,470
Per week:$10,286
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Apartment
1 / 41

Gloucester Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

from

$164

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$164 - $179
Per week:$1,148 - $1,250
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 17

Gloucester Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$425

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$425 - $605
Per week:$2,100 - $2,920
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 39

Gloucester Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$286

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$286 - $404
Per week:$2,000 - $2,828
Pets allowed:No
Internet:Yes

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....

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Gloucester Massachusetts Vacation Rentals - Apartment
1 / 13

Gloucester Apartment
1 Bedroom / 1 Bathroom / Sleeps 3
Apartment / 1 Bedroom / Sleeps 3

from

$190

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$190
Per week:$1,330
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 36

Gloucester Home
5 Bedrooms / 2 Bathrooms / Sleeps 9
Home / 5 Bedrooms / Sleeps 9

from

$450

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:9
Type:Home
Per night:$450 - $645
Per week:$2,200 - $3,034
Pets allowed:No
Internet:Yes

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 ...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 32

Gloucester Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$400 - $605
Per week:$2,000 - $2,763
Pets allowed:Yes
Internet:Yes

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, ...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 20

Gloucester Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,100 - $1,500
Per week:$5,500 - $7,560
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Cottage
1 / 16

Gloucester Cottage
5 Bedrooms / 2 Bathrooms / Sleeps 9
Cottage / 5 Bedrooms / Sleeps 9

from

$525

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:9
Type:Cottage
Per night:$525 - $770
Per week:$2,625 - $3,650
Pets allowed:No
Internet:Yes

WALK TO GOOD HARBOR BEACH from this perfect beach goer’s destination, Somersette. A classic 5 bedroom, 2 bath summer cottage located in the exclusive private beach community of Brier Neck, which is just 0. 1 miles from the sands of Good Harbor Beach, and offers stunning views...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 34

Gloucester Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$600

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$600 - $800
Per week:$3,000 - $4,062
Pets allowed:No
Internet:Yes

This immaculate home has it all: prime Good Harbor Beach location, views, historic charm and modern comfort and style. The original cottage was built as a stone carriage house to a neighboring estate. A wonderful octagonal addition has created a three bedroom/two full bath home ...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 20

Gloucester Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$146

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$146 - $154
Per week:$1,021 - $1,072
Pets allowed:No
Internet:Yes

Welcome, cher ami ("dear friend"), to this gleaming and immaculate, second floor remodeled two plus bedroom unit which is also available as a seasonal rental. If you would like to come for at least two weeks to enjoy the multitude of delights that Cape Ann has to offer, this could...

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Gloucester Massachusetts Vacation Rentals - Apartment
1 / 11

Gloucester Apartment
2 Bedrooms / 1 Bathroom / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$225 - $330
Per week:$1,050 - $1,513
Pets allowed:No
Internet:Yes

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-...

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Living area, kitchen and spiral stairs to second floor
1 / 27

Gloucester Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$235

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$235 - $385
Per week:$1,300 - $1,721
Pets allowed:Yes
Internet:Yes

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 ...

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Gloucester Massachusetts Vacation Rentals - Apartment
1 / 23

Gloucester Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 8
Apartment / 3 Bedrooms / Sleeps 8

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Apartment
Per night:$350 - $450
Per week:$1,650 - $2,294
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 17

Gloucester Home
3 Bedrooms / 1 Bathroom / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Home
Per night:$250 - $358
Per week:$1,150 - $1,617
Pets allowed:Yes
Internet:Yes

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, ...

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Gloucester Massachusetts Vacation Rentals - Apartment
1 / 31

Gloucester Apartment
3 Bedrooms / 3 Bathrooms / Sleeps 10
Apartment / 3 Bedrooms / Sleeps 10

from

$650

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:10
Type:Apartment
Per night:$650
Per week:$2,450 - $3,342
Pets allowed:No
Internet:Yes

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...

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About Gloucester

Gloucester, MA Travel Tips

Located on Cape Ann on the North Shore of Massachusetts is the city of Gloucester. This picturesque seaport city is a popular destination for people who vacation in MA. It is an attractive city with much of its appeal in its historic charm. A great way to immerse one’s family in the culture and history of the city is to stay in a Gloucester rental. At Vacation Home Rentals, we list an assortment of Gloucester, MA, rentals on our site. Our for-rent-by-owner homes are some of the best properties that are available online. Rentals listed on our site are well-maintained and affordable. As a result, a rental will save tourists money and do away with the frustration that can come with staying in a hotel. To also help reduce frustration, parents will want to create an itinerary for their trip. An itinerary will ensure that there are always activities for everyone, regardless of age. Transportation is another area that requires some advance thought. If driving, take the cost of parking at various attractions into consideration. Alternative transportation can be a solution during your stay. Some people who stay in Gloucester, MA, vacation rentals may consider walking to be a viable option in some cases. Other transportation options include the Water Shuttle or the Gloucester Trolley Shuttle.

Attractions

The activities and attractions in the city are a part of the allure for vacationing families. Following a good night’s rest in their Gloucester vacation rentals, tourists have plenty to see and do. Beaches in Gloucester are some of the most popular and enticing attractions for tourists. Beaches that you and your family can enjoy include Cressey’s Beach and Wingaersheek Beach. Lighthouses are also a popular attraction for visitors who stay in vacation rentals. Gloucester, MA, lighthouses include Annisquam Harbor Light Station, Eastern Point Light Station, and Ten Pound Island Light. Also while in Gloucester, families won’t want to miss the whales. There are many tour companies that offer whale-watching tours and boat charters. Another historic and unforgettable attraction is the eight-foot Gloucester Fisherman’s Memorial. The memorial is in memory of fishermen who lost their lives to the sea. Also in Gloucester, visit the Cape Ann Museum and Beauport. The Hammond Castle Museum, another popular attraction, is open to the public and allows self-guided tours.

Events

It isn’t only the ...

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