Gloucester Vacation Rentals

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4BR / 2BA - Sleeps 8 - Gloucester Home

Located in the Private Section of Wingaersheek Beach (Coffin's Beach)and just a 3 minute walk to to the...

$465 / nt

4 Reviews
Front of our home
Ed

3BR / 1.5BA - Sleeps 8 - Gloucester Home

Ours is a wonderful home. It's on a hill and 3- acres of woods and lawns overlooking Lobster Cover. Gloucester...

$315 / nt

1 Review
Gloucester Massachusetts Vacation Rentals - Townhouse

3BR / 2BA - Sleeps 7 - Gloucester Townhouse

Walk to Gloucester's best beach - Good Harbor just 2/10 mile from this wonderful duplex offering 3 air...

$400 / nt

5BR / 1BA - Sleeps 6 - Gloucester Cottage

The cottage is an updating of the original Coggeshall artist camp overlooking a grassy acre of land leading...

$279 / nt

Cottage from the shore
Bruce

4BR / 1BA - Sleeps 6 - Gloucester Cottage

Updated seasonal waterfront cottage ideal for swimming or kayaking right from the property. It is located...

$315 / nt

Gloucester Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 8 - Gloucester Home

Direct waterfront on picturesque Goose Cove, this immaculate property provides endless delights, both...

1 Review
Gloucester Massachusetts Vacation Rentals - Home

1BR / 2BA - Sleeps 2 - Gloucester Home

Tucked away behind the owner's home, this attached East Gloucester cottage is a perfect retreat after...

Gloucester Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 10 - Gloucester Home

This delightful and charming home is ideally situated just one block from Good Harbor Beach overlooking...

Gloucester Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 10 - Gloucester Home

This stately home perched on the dramatic coast of East Gloucester, known locally as “Bass Rocks”,...

Gloucester Massachusetts Vacation Rentals - Home

5BR / 2BA - Sleeps 9 - Gloucester Home

Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this...

Gloucester Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Gloucester Home

NEW! Just 2/10 of a mile from the white sands and surf of Coffins Beach making this immaculate 4 bedroom/2...

Gloucester Massachusetts Vacation Rentals - Apartment

5BR / 2BA - Sleeps 8 - Gloucester Apartment

This well appointed 3 bedroom/ 2 bath pied a'terre is perched above the picturesque waterfront Stacey...

Gloucester Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Gloucester Home

This delightful 3 bedroom, 1. 5 bath Queen Anne style home is bright and cheery and just waiting for...

Gloucester Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Gloucester Home

"Simply gorgeous! " You’ll think as you step into this pristine home. Immediately upon entering,...

Gloucester Massachusetts Vacation Rentals - Cottage

2BR / 2BA - Sleeps 6 - Gloucester Cottage

Featuring a waterfront location, 2 bedrooms, 2 baths, and the option to rent the adjacent 3 bedroom,...

Gloucester Massachusetts Vacation Rentals - Cottage

3BR / 2BA - Sleeps 6 - Gloucester Cottage

This sweet and comfortable waterfront cottage with spectacular sunset views over the Annisquam River...

Gloucester Massachusetts Vacation Rentals - Home

3BR / 1BA - Sleeps 6 - Gloucester Home

A delightful home situated in Gloucester's charming Bay View neighborhood, Annie’s Place radiates...

Gloucester Massachusetts Vacation Rentals - Home

2BR / 2BA - Sleeps 4 - Gloucester Home

This charming cottage is located on a quiet side street in Gloucester's fabled artist colony of Rocky...

Gloucester Massachusetts Vacation Rentals - Apartment

1BR / 1BA - Sleeps 3 - Gloucester Apartment

Good Harbor Beach! Friday to Friday rental! Step out the door, walk over the Good Harbor Beach footbridge...

Gloucester Massachusetts Vacation Rentals - Apartment

1BR / 1BA - Sleeps 2 - Gloucester Apartment

Located in Gloucester’s Rocky Neck Cultural District, this charming one bedroom waterfront retreat...

Gloucester Massachusetts Vacation Rentals - Cottage

6BR / 4BA - Sleeps 10 - Gloucester Cottage

NEW! This 6 bedroom/4 bath home has nothing "cottagey" about it and it is situated on the highest point...

Gloucester Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Gloucester Home

Walk to Gloucester's best beach - Good Harbor, located just 0. 2 miles from this wonderful duplex,...

Gloucester Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Gloucester Home

NEW! This bright and open contemporary home was custom designed and built by the architect owner and...

Gloucester Massachusetts Vacation Rentals - Home

5BR / 3BA - Sleeps 8 - Gloucester Home

This is your beachfront July getaway! Take your private path directly onto the white sands of Coffins...

Gloucester Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Gloucester Home

THREE MONTH MINIMUM RENTAL. Make this immaculate 3 bedroom/2. 5 bath town home your home for this summer...

Gloucester Massachusetts Vacation Rentals - Cottage

3BR / 3BA - Sleeps 5 - Gloucester Cottage

WINTER RENTAL - 3 bedrooms and 2. 5 baths available 9/15- 5/31. Enjoy the water views from this delightful...

Gloucester Massachusetts Vacation Rentals - Home

2BR / 3BA - Sleeps 4 - Gloucester Home

NEW! Direct waterfront with a deep water dock perfect for boating, swimming or just relaxing while...

Gloucester Massachusetts Vacation Rentals - Home

2BR / 2BA - Sleeps 4 - Gloucester Home

Enjoy the views, breezes and smell of the sea from this lofty perch overlooking Gloucester's famed waterfront...

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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