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Gloucester Apartments & Vacation Rentals - 59 Rentals Available

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59 Vacation rentals

1 / 31

Gloucester Cottage

  • 7
  • 12
  • 3 nights min
  • Ask about children

$1,723.00

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from $1,723.00 / night

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1 / 16

Gloucester Apartment

  • 2
  • 4
  • 6 nights min
  • Ask about children

$361.00

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from $361.00 / night

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1 / 20

Gloucester House

  • 3
  • 8
  • 7 nights min
  • Child friendly

$769.00

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from $769.00 / night

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1 / 44

Gloucester House

  • 4
  • 10
  • 6 nights min
  • Child friendly

$894.00

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from $894.00 / night

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1 / 49

Gloucester House

  • 5
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,369.00

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from $1,369.00 / night

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1 / 33

Gloucester House

  • 4
  • 7
  • 3 nights min
  • Child friendly

$1,021.00

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from $1,021.00 / night

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1 / 29

Gloucester Cottage

  • 3
  • 6
  • 3 nights min
  • Child friendly

$627.00

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from $627.00 / night

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1 / 49

Gloucester House

  • 4
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$1,104.00

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from $1,104.00 / night

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1 / 22

Gloucester House

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Pet friendly

$495.00

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from $495.00 / night

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1 / 20

Gloucester House

  • 5
  • 10
  • 6 nights min
  • Child friendly
  • Pet friendly

$710.00

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from $710.00 / night

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1 / 36

Gloucester House

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning

$763.00

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from $763.00 / night

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1 / 28

Gloucester House

  • 3
  • 8
  • 3 nights min
  • Child friendly
  • Air conditioning

$982.00

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from $982.00 / night

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1 / 33

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Pet friendly

$982.00

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from $982.00 / night

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1 / 53

Gloucester House

  • 6
  • 16
  • 3 nights min
  • Child friendly

$1,694.00

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from $1,694.00 / night

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1 / 23

Gloucester House

  • 3
  • 8
  • 6 nights min
  • Child friendly

$643.00

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from $643.00 / night

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1 / 14

Gloucester House

  • 3
  • 9
  • 3 nights min
  • Ask about children
  • Pet friendly

$668.00

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from $668.00 / night

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1 / 23

Gloucester House

  • 3
  • 7
  • 3 nights min
  • Child friendly
  • Pet friendly

$563.00

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from $563.00 / night

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1 / 16

Gloucester Apartment

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Air conditioning

$497.00

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from $497.00 / night

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1 / 35

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning

$814.00

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from $814.00 / night

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1 / 40

Gloucester House

  • 3
  • 8
  • 3 nights min
  • Child friendly
  • Air conditioning

$899.00

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from $899.00 / night

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1 / 12

Gloucester Apartment

  • 1
  • 3
  • 6 nights min
  • Ask about children

$292.00

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from $292.00 / night

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1 / 39

Gloucester House

  • 4
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,169.00

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from $1,169.00 / night

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1 / 44

Gloucester House

  • 6
  • 14
  • 3 nights min
  • Child friendly
  • Pet friendly

$1,422.00

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from $1,422.00 / night

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1 / 35

Gloucester House

  • 3
  • 6
  • 6 nights min
  • Child friendly
  • Air conditioning

$610.00

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from $610.00 / night

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1 / 17

Gloucester House

  • 4
  • 8
  • 3 nights min
  • Ask about children

$1,283.00

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from $1,283.00 / night

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(1)

1 / 27

Gloucester House

  • 2
  • 5
  • 3 nights min
  • Ask about children

$493.00

Excellent (1 reviews)

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from $493.00 / night

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1 / 37

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Air conditioning

$739.00

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from $739.00 / night

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1 / 30

Gloucester House

  • 3
  • 4
  • 31 nights min
  • Ask about children

$243.00

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from $243.00 / night

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1 / 33

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Pet friendly

$571.00

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from $571.00 / night

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1 / 30

Gloucester House

  • 4
  • 8
  • 3 nights min
  • Ask about children
  • Air conditioning

$992.00

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from $992.00 / night

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1 / 15

Gloucester Cottage

  • 3
  • 5
  • 3 nights min
  • Ask about children
  • Pet friendly

$524.00

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from $524.00 / night

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1 / 27

Gloucester House

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Pet friendly

$687.00

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from $687.00 / night

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Your search has been expanded 5.7 miles to include more rentals

(4)

1 / 46

Rockport House - 3.1 miles away

  • 4
  • 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“The house was beautiful, well kept, maintained and in a terrific location!!! It had everything a vacationer would need and want for a relaxing time. My family and I look forward to making this home an annual vacation spot...”
- Review left on 08/29/2016

$687.00

Excellent (4 reviews)

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from $687.00 / night

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(8)

1 / 35

Rockport Cottage - 3.1 miles away

  • 4
  • 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“This is a home that provides all you need for a wonderful vacation seaside. It has a peaceful and serene quality to it by virtue of its location and decor. Bedrooms are spacious and modern and the living space is open and comfortable. Most necessary...”
- Review left on 06/15/2016

$516.00

Excellent (8 reviews)

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from $516.00 / night

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1 / 21

Rockport House - 4 miles away

  • 7
  • 14
  • 7 nights min
  • Child friendly

$729.00

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from $729.00 / night

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1 / 17

Rockport Cottage - 4.3 miles away

  • 1
  • 4
  • 3 nights min
  • Ask about children

$401.00

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from $401.00 / night

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1 / 21

Rockport House - 4 miles away

  • 2
  • 4
  • 3 nights min
  • Ask about children
  • Pet friendly

$563.00

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from $563.00 / night

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(1)

1 / 22

Rockport House - 3.5 miles away

  • 2
  • 4
  • 3 nights min
  • Ask about children

$459.00

Excellent (1 reviews)

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from $459.00 / night

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1 / 23

Manchester-by-the-Sea House - 5.7 miles away

  • 4
  • 8
  • 6 nights min
  • Ask about children
  • Pet friendly

$880.00

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from $880.00 / night

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1 / 34

Rockport House - 3.9 miles away

  • 4
  • 7
  • 3 nights min
  • Child friendly
  • Pet friendly

$609.00

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from $609.00 / night

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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. 

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