Gloucester Vacation Rentals, Homes, & More

1-40 of 40 Gloucester Rentals

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Gloucester Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 7

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Townhouse
Per night:$400
Per month:$12,000
Pets allowed:No
Internet:No

Walk to Gloucester's best beach - Good Harbor just 2/10 mile from this wonderful duplex offering 3 air conditioned bedrooms and two full custom tile baths with showers. Enter into the open concept living, dining and kitchen areas with parquet floors which is the perfect place for...

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1 / 9

Gloucester Cottage
3 Bedrooms / 1 Bathroom / Sleeps 6

Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Cottage
No rental rates available - please contact the owner
 
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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Gloucester Massachusetts Vacation Rentals - Home
1 / 52

Gloucester Home
4 Bedrooms / 1.5 Bathrooms / Sleeps 7

“ 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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Front Left
1 / 14

Gloucester Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”4 Reviews

from

$465

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$465
Per week:$3,250
Pets allowed:No
Internet:Yes

Located in the Private Section of Wingaersheek Beach (Coffin's Beach)and just a 3 minute walk to to the beach. Enjoy this totally renovated 4 bedroom ranch house with all the comforts of home! Central air, washer/dryer, fully equipped kitchen with sliders leading to a deck with...

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Retraction

“ Excellent ”
July 14, 2014
I recently reported I received no response from the owner. She did in fact try to make contact with me. For some reason her email didn't go through. So I retract my previous poor review!I didn't stay there but I know the property and the beach-- both lovely!Tim
Tim Murphy, Boston

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Cottage from the shore
1 / 6

Gloucester Cottage
4 Bedrooms / 1 Bathroom / 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

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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Front of the Colonial house.
1 / 8
Bedrooms:4
Bathrooms:2
Sleeps:12
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

7 Minutes walk to Downtown or train to Boston. Ideal quiet location & just minutes walk to 2 beaches. Weekly & Monthly Rentals Only Must Be Booked Months In Advance Of Arrival Date. I never do Daily rentals 4 Bedrooms, 3 with King sized beds. 2 Full Tub/Shower bathrooms. ...

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july rental

“ Excellent ”
July 22, 2013
We had a family wedding I'm Gloucester and planned sn extended stay. This home was ideally located to restaurants- beaches and the downtown area. The home was clean and wad able to accomadate 12 people easily. The owner was a pleasureto work with. We had a well stocked refrigerator and all linens and towels were provided. The neighborhood was very quiet and a short walk to the water and good local restaurants. Highly recommend this home.
Gerald Siegal, Berlin Ct

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Living area, kitchen and spiral stairs to second floor
1 / 24

Gloucester Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$235

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$235 - $259
Per week:$1,300 - $1,792
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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aerial view
1 / 44

Gloucester Home
6 Bedrooms / 6 Bathrooms / Sleeps 16

from

$700

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:16
Type:Home
Per night:$700 - $908
Per week:$3,750 - $6,510
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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Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Home
Per night:$300 - $375
Per week:$2,100 - $3,150
Pets allowed:No
Internet:Yes

This large, comfortable family home is just steps from the white sands of Long Beach- - a perfect summer location! Although we don't brag about its view, the location is superb! Built in the early 1900's, much of its early charm still remains but is augmented with an updated ...

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Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$510 - $605
Per week:$2,700 - $4,270
Pets allowed:Yes
Internet:Yes

Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2. 5 bath home situated in Gloucester’s cultural district known as Rocky Neck, will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious sunrises, the views...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 33

Gloucester Home
6 Bedrooms / 4 Bathrooms / Sleeps 10

from

$858

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:10
Type:Home
Per night:$858 - $1,195
Per week:$6,000 - $8,360
Pets allowed:No
Internet:Yes

Astounding views! This 6 bedroom/4 bath home has nothing "cottagey" about it and it is situated on the highest point of Brier Neck with views from every angle and a 5 minute walk (on quiet side streets) will take you to the surf and sands of Good Harbor OR Long Beaches, arguably...

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Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$786
Per week:$5,500
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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Gloucester Massachusetts Vacation Rentals - Home
1 / 31

Gloucester Home
4 Bedrooms / 2 Bathrooms / Sleeps 10

from

$565

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$565
Per week:$3,500 - $4,725
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 is completely furnished with high quality and attractive furnishings. Enter into the center...

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Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
5 Bedrooms / 2 Bathrooms / Sleeps 9

from

$420

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:9
Type:Home
Per night:$420 - $495
Per week:$2,200 - $3,500
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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Bedrooms:5
Bathrooms:3
Sleeps:9
Type:Home
Per night:$1,100
Per week:$5,150 - $6,900
Pets allowed:No
Internet:No

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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Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$375

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$375 - $440
Per week:$1,875 - $3,150
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 / 17
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$400 - $425
Per week:$2,100 - $3,325
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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Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$300
Per week:$1,500 - $2,200
Pets allowed:Yes
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Apartment
1 / 23

Gloucester Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Apartment
Per night:$350 - $450
Per week:$1,650 - $2,420
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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Bedrooms:3
Bathrooms:5
Sleeps:8
Type:Home
Per night:$943
Per week:$6,600
Pets allowed:No
Internet:Yes

RENTING FOR AUGUST 2015. Ocean Whisper House is the high end, waterfront, air conditioned beauty 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 - Home
1 / 12

Gloucester Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$390

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$390
Per month:$11,700
Pets allowed:No
Internet:Yes

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,...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 37

Gloucester Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$440

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$440 - $450
Per week:$2,325 - $3,675
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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Gloucester Massachusetts Vacation Rentals - Home
1 / 38

Gloucester Home
5 Bedrooms / 3 Bathrooms / Sleeps 8

from

$621

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:8
Type:Home
Per night:$621
Per week:$4,342
Pets allowed:No
Internet:Yes

This is your beachfront July getaway! Take your private path directly onto the white sands of Coffins Beach with 5 bedrooms and 2. 5 baths. This comfortable family home has tons of space both inside and out. Enter the house into the updated kitchen with stainless appliances including...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,050 - $1,210
Per week:$5,500 - $8,750
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 / 12

Gloucester Cottage
2 Bedrooms / 4 Bathrooms / Sleeps 7

from

$400

/ night

Email Owner
Bedrooms:2
Bathrooms:4
Sleeps:7
Type:Cottage
Per night:$400 - $500
Per week:$1,800 - $3,360
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
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$200
Per month:$6,000
Pets allowed:Yes
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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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$307
Per week:$2,145
Pets allowed:No
Internet:Yes

This lovely three bedroom/ two bath Victorian brings you back to an era when life was more serene and relaxed. In this idyllic and private area with woods on two sides, one can sit on the wraparound farmer's porch or on the screened porch, overlooking a glimmering lily pond, and...

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$286
Per week:$2,000 - $3,025
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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Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$1,572
Per week:$11,000
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 - Home
1 / 17

from

$220

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Home
Per night:$220 - $275
Per week:$1,150 - $1,855
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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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$600 - $770
Per week:$3,000 - $4,345
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 - Cottage
1 / 28
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$215 - $299
Per week:$1,500 - $2,090
Pets allowed:No
Internet:Yes

This sweet and comfortable waterfront cottage with spectacular sunset views over the Annisquam River offers a wonderful New England retreat. Swim and kayak from the property or even fish off the deepwater dock, which can accommodate boats up to 18' and has a ladder on the side to...

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Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$210 - $248
Per week:$1,050 - $1,750
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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Gloucester Massachusetts Vacation Rentals - Home
1 / 44
Bedrooms:2
Bathrooms:3
Sleeps:4
Type:Home
Per night:$500 - $550
Per week:$2,500 - $4,130
Pets allowed:No
Internet:Yes

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...

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Bedrooms:3
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$150 - $165
Per week:$850 - $1,365
Pets allowed:Yes
Internet:Yes

Bring your boat (or use the kayak provided) or swim from the dock of this sweet little cottage. 3 Bedrooms comfortably sleep 4. Water views, ingenious use of space and cozy décor combine to give the feel of floating in a well- fitted vessel. A former fisherman's cottage on Walker...

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Gloucester Massachusetts Vacation Rentals - Apartment
1 / 16

Gloucester Apartment
1 Bedroom / 1 Bathroom / Sleeps 3

from

$198

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$198
Per week:$1,384
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 - Apartment
1 / 12
Bedrooms:2
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$150 - $165
Per week:$600 - $661
Pets allowed:No
Internet:Yes

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...

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Gloucester Massachusetts Vacation Rentals - Home
1 / 9

Gloucester Home
1 Bedroom / 2 Bathrooms / Sleeps 2

from

$157

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$157
Per week:$1,100 - $1,375
Pets allowed:No
Internet:No

Tucked away behind the owner's home, this attached East Gloucester cottage is a perfect retreat after a day of lounging on Good Harbor Beach, less than 1/4 mile away. A separate driveway, perennial gardens, and lawn provide shade and privacy. The property is self- contained with...

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Gloucester Massachusetts Vacation Rentals - Apartment
1 / 41
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$134 - $179
Per week:$933 - $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, 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 atmosphere and year-round attractions that draw people to Gloucester. Tourists often come and stay in Gloucester rentals when there is an event taking place. The city sees many events throughout the year. When visiting in July, families won’t want to miss the Fishtown Horribles Parade. The Gloucester Blues Festival and the Gloucester Waterfront Festival take place in August. Another August event not to miss is the annual Gloucester Schooner Festival. During this festival, the entire family will enjoy seeing various schooners. If staying in a Gloucester rental in mid-September, a fun event to take part in is the Downtown Gloucester Block Party. Also in September, bike racing enthusiasts staying in Gloucester, MA, vacation rentals won’t want to miss the two-day Gran Prix of Gloucester.
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