Gloucester Vacation Rentals, Homes, & More

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Gloucester Massachusetts Vacation Rentals - Home
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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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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Gloucester Massachusetts Vacation Rentals - Home
1 / 16

Gloucester Home
3 Bedrooms / 1.5 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$315

/ night

Email Owner
Bedrooms:3
Bathrooms:1.5
Sleeps:8
Type:Home
Per night:$315
Per week:$2,200
Pets allowed:No
Internet:Yes

Ours is a wonderful home. It's on a hill and 3- acres of woods and lawns overlooking Lobster Cover. Gloucester and Rockport are nearby and lovely places to stroll, dine and enjoy music. Boston's an easy train ride away and the highway's nearby as well. The 100- year old...

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peace

“ Excellent ”
September 1, 2014
Visited daughter in Massachusetts and my Mom joined me. Beautiful VRBO on 3 acres. Lots of scrabble and a local theatre company in Gloucester.
Les Haldane, hi

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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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Gloucester Massachusetts Vacation Rentals - Home
1 / 8

Gloucester Home
4 Bedrooms / 2 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:12
Type:Home
Per night:$358
Per week:$2,500
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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Gloucester Massachusetts Vacation Rentals - Cottage
1 / 4

Gloucester Cottage
5 Bedrooms / 1 Bathroom / Sleeps 6

from

$279

/ night

Email Owner
Bedrooms:5
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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Gloucester Massachusetts Vacation Rentals - Townhouse
1 / 11

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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Gloucester Massachusetts Vacation Rentals - Cottage
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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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
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, sandbars Walk from this four bedroom house, ...

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Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$235 - $259
Per week:$1,300 - $1,900
Pets allowed:Yes
Internet:Yes

Enjoy the views, breezes and smell of the sea from this lofty perch overlooking Gloucester's famed waterfront Stacey Boulevard which is centered by the iconic "Gloucester Fisherman at the Wheel" sculpture - a symbol of the fishing port's rich history, both as a working waterfront...

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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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