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Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
4 BR / 1.5 BA / Sleeps 7 4 7 Min stay varies
Home / 4 Bedrooms / Sleeps 7
4 bedrooms 1.5 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
Addition of new windows, insulation, Heat & Central Air Conditioning now extends our season March 1 to December 31. This newly renovated and updated waterfront gem has four bedrooms and 1. 5 baths, a deep- water dock ...
(4) Excellent (4 reviews)
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Gloucester Cottage
3 BR / 1 BA / Sleeps 7 3 7 7 night min stay
Cottage / 3 Bedrooms / Sleeps 7
3 bedrooms 1 bathroom Sleeps 7
High Speed Internet • Microwave • Washer/Dryer
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 swimm...
(1) Excellent (1 review)
Cottage from the shore
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Gloucester Cottage
4 BR / 1 BA / Sleeps 6 4 6 7 night min stay
Cottage / 4 Bedrooms / Sleeps 6
4 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
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 t...
Exterior View
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Gloucester Home
4 BR / 3 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Sun when you want it. Shade when you need it. Cool Cove is a beach house that has it all. Jutting high above Wingaersheek Beach on a promontory from which it seems that you can see forever: Annisquam Lighthouse, Ipswich...
House exterior.
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Gloucester Home
5 BR / 3 BA / Sleeps 10 5 10 7 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This large, comfortable family- oriented vacation home is just steps from the white sands of Long Beach- - a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented w...
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Gloucester Home
3 BR / 1 BA / Sleeps 5 3 5 Min stay varies
Home / 3 Bedrooms / Sleeps 5
3 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Microwave • Washer/Dryer
Enjoy this comfortable recently renovated 3 bedroom, 1 bath vacation home conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort ...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
2 BR / 1 BA / Sleeps 4 2 4 14 night min stay
Home / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
Welcome, cher ami ("dear friend"), to this gleaming and immaculate, second floor vacation rental. Cher Ami is available as a summer rental and an off- season rental, with a minimum 2- week rental period. Comprising t...
Gloucester Massachusetts Vacation Rentals - Cottage
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Gloucester Cottage
7 BR / 4 BA / Sleeps 12 7 12 7 night min stay
Cottage / 7 Bedrooms / Sleeps 12
7 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Golden Sands is the quintessential turn of the century Gloucester beach "cottage. " With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, ...
View of Salt Island and Good Harbor Beach
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Gloucester Home
3 BR / 4 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 4 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This immaculate 3 bedroom, 3. 5 bath luxury vacation rental home is the ultimate beach getaway. Incredible 180 degree views...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
4 BR / 3 BA / Sleeps 10 4 10 3 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Microwave • TV (Antenna)
New in 2016! Your family will love this extraordinary waterfront 4 bedroom/3 full bath vacation rental home with spectacular views set on a bluff over picturesque Strawberry Cove and the open Atlantic. Views abound from...
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Gloucester Home
6 BR / 5 BA / Sleeps 10 6 10 Min stay varies
Home / 6 Bedrooms / Sleeps 10
6 bedrooms 5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This luxurious vacation rental home is situated on the highest point of Brier Neck with astounding ocean views from every angle. Ascend the outside steps of this Tudor- style home and observe the rolling lawn on one side...
Rear view with yard and deck.
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Gloucester Home
6 BR / 6 BA / Sleeps 16 6 16 7 night min stay
Home / 6 Bedrooms / Sleeps 16
6 bedrooms 6 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
This spacious and gracious vacation rental home offers incredible versatility to suit your specific vacation needs. The house can accommodate just your family or your extended group of up to 16, making it the perfect su...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
3 BR / 2 BA / Sleeps 7 3 7 Min stay varies
Home / 3 Bedrooms / Sleeps 7
3 bedrooms 2 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
This delightful 3 bedroom, 1. 5 bath Queen Anne- style vacation rental home is bright and cheery and just waiting for you! Enter the house into the kitchen from the verdant and sizable back yard (or choose one of the o...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
3 BR / 2 BA / Sleeps 6 3 6 3 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This immaculate beach house 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 wonderfu...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
4 BR / 3 BA / Sleeps 10 4 10 7 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2. 5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point t...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
4 BR / 3 BA / Sleeps 7 4 7 3 night min stay
Home / 4 Bedrooms / Sleeps 7
4 bedrooms 3 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
New in 2016! Enjoy views of Gloucester's outer harbor, and the private sandy beach, across the quiet private road from almost every room in this fantastic vacation rental home. There are two glorious slate patios that...
Gloucester Massachusetts Vacation Rentals - Cottage
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Gloucester Cottage
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Cottage / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Microwave • TV (Antenna)
Featuring a waterfront location, 2 bedrooms, and 2 baths, Water’s Edge Too makes for the perfect family getaway. As you sit out on the screen porch, peacefully gazing out over gorgeous Goose Cove, you will sense t...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
New in 2016! Ideally situated between two of Cape Ann's most beautiful beaches, this immaculate and newly renovated vacation rental home is a mere 3 minute walk to Long Beach and an 8 minute walk to Good Harbor. After ...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
11 BR / 10 BA / Sleeps 20 11 20 7 night min stay
Home / 11 Bedrooms / Sleeps 20
11 bedrooms 10 bathrooms Sleeps 20
High Speed Internet • Microwave • TV (Antenna)
From the instant one enters StoneAcre through its massive, intricately carved and electronically controlled outer gates, the estate evokes the romance and luxury of an opulent, bygone era while offering virtually ever...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
3 BR / 2 BA / Sleeps 6 3 6 3 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
New in 2016! You can have it all with Ships Bell House, as this immaculate 3 bedroom/ 2 full bath vacation rental home enjoys amazing water views, including fantastic sunsets. The home has the added bonus of a pass to...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
3 BR / 3 BA / Sleeps 6 3 6 90 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Make this immaculate 3 bedroom/2. 5 bath town home your vacation home for the summer! This home is a 3- month minimum rental. The main floor has gleaming hardwood throughout the formal foyer and open floor plan kitchen,...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
4 BR / 2 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Air Conditioning
New in 2016! Your Point of View will be forever changed, for the better, once you have had the opportunity to stay in this magnificently situated beachfront vacation rental home. This contemporary, fully air- conditi...
Gloucester Massachusetts Vacation Rentals - Home
1 / 32

Gloucester Home
4 BR / 3 BA / Sleeps 10 4 10 Min stay varies
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Location, location, location! Waterviews & a short walk to Good Harbor Beach. This four bedroom/2. 5 bath vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The ...
Gloucester Massachusetts Vacation Rentals - Cottage
1 / 19

Gloucester Cottage
3 BR / 4 BA / Sleeps 7 3 7 Min stay varies
Cottage / 3 Bedrooms / Sleeps 7
3 bedrooms 4 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
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 ev...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
5 BR / 2 BA / Sleeps 9 5 9 Min stay varies
Home / 5 Bedrooms / Sleeps 9
5 bedrooms 2 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian vacation rental home has been in the same family since the 1880's. Fro...
Gloucester Massachusetts Vacation Rentals - Home
1 / 32

Gloucester Home
5 BR / 2 BA / Sleeps 10 5 10 3 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
New in 2016! Enjoy the best sunsets on the East Coast from this classic riverfront Victorian summer retreat. Annisquam Singing Pines offers everything you could want in a vacation rental home, with five bedrooms, two ...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
1 BR / 1 BA / Sleeps 4 1 4 Min stay varies
Home / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
Walk to Good Harbor in 7 minutes from this NEW one bedroom apartment. Completed in July of 2015, this vacation home is pristine and waiting just for you. Enter through your own entrance into the bright granite kitchen w...
Gloucester Massachusetts Vacation Rentals - Home
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Gloucester Home
3 BR / 1 BA / Sleeps 6 3 6 3 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
A delightful vacation home situated in Gloucester's charming Bay View neighborhood, Annie's Place radiates an aura of sun and warmth. Only an 8 minute walk to lovely Plum Cove Beach, Annie's Place lets you spend your s...
Gloucester Massachusetts Vacation Rentals - Apartment
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Gloucester Apartment
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Apartment / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • TV (Antenna)
Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2. 5 baths. The aptly na...
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About Gloucester

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 Massachusetts, especially during the summer. Gloucester bursts with historic charm, and a great way to immerse oneself in the area’s culture and history is to stay in one of the many appealing, well-preserved Gloucester vacation rentals. 

Climate

Like most cities in Massachusetts, Gloucester experiences all four seasons and sees warm summers and cold, snowy winters. July is typically the warmest month with temperatures in the 70s, while January is usually the coldest with temperatures that can dip into the 20s. To make the most of a vacation in this part of Massachusetts, choose Gloucester vacation rentals that are available during the summer for the most pleasant stay. 

Transit

Transportation for getting around Gloucester does require some advance thought before your arrival. Driving is the easiest way to get around the area, but keep in mind the cost of parking at various attractions, such as the local beaches. To save money, park for free at Stage Fort Park and then take the Trolley Shuttle, which runs on weekends from June 15 through Labor Day. The Gloucester Water Shuttle is another great way to get as it connects Gloucester’s two Cultural Districts, Harbortown and Rocky Neck. The shuttle is only $10 to ride all day.   

Things to do

Gloucester boasts a variety of activities and attractions that are part of the allure for vacationing families in this area. The city’s beaches are some of the most popular in New England and include Good Harbor Beach, Cressey’s Beach and Wingaersheek Beach. Swimming, surfing, sunbathing, and shelling are all popular activities at Gloucester’s pristine, white-sand beaches and secluded coves. The shoreline also is home to numerous lighthouses, which are popular attractions for those staying in Gloucester vacation rentals. Some area lighthouses include Annisquam Harbor Light Station, Eastern Point Light Station, and Ten Pound Island Light.

For history buffs, the eight-foot Gloucester Fisherman’s Memorial Monument is a poignant reminder of how dangerous fishing was and it was built in memory of fishermen who lost their lives to the sea. Other historic attractions worth visiting are the Cape Ann Museum, Beauport, and the Sargent House Museum, which is located in the heart of the downtown area and pays tribute to Gloucester’s historic past. On a rainy day, take a self-guided tour through the medieval Hammond Castle. 

Events

It isn’t only the atmosphere and local attractions that draw vacationers to Gloucester. People often come and stay in Gloucester vacation rentals to experience some of the city’s unique annual events. When visiting in July, families won’t want to miss the Fishtown Horribles Parade. The parade is an enduring tradition that features costumes and skits made up by individuals to have fun. The following month brings the Gloucester Schooner Festival during which families will enjoy seeing various schooners gliding through the coastal waters. The Gloucester Blues Festival and the Gloucester Waterfront Festival also take place in August. If staying in the area through September, take part in the Downtown Gloucester Block Party or watch bike racing enthusiasts during the two-day Gran Prix of Gloucester.

From sandy beaches and picturesque lighthouses to historic attractions and lively events, Gloucester is an ideal New England vacation destination. Come here to enjoy the slower pace of life and unique attractions that have been thriving for years in this beautiful setting.