Gloucester Apartments & Vacation Rentals - 59 Rentals Available
59 Vacation rentals

Golden Sands at Good Harbor: Across the street from the beach
Gloucester Cottage
- 7 bedrooms 7
- 3 bathrooms
- sleeps 12 12
- 3 nights min
- Ask about children
$1,724.00
from $1,724.00 / night

Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 6 nights min
- Ask about children
$361.00
from $361.00 / night

Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Child friendly
$769.00
from $769.00 / night

Seaside House: Good Harbor Beach and the Back Shore right outside your door.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 6 nights min
- Child friendly
$894.00
from $894.00 / night

Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
$1,369.00
from $1,369.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$1,021.00
from $1,021.00 / night
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
$627.00
from $627.00 / night
Magnolia Tides: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$1,167.00
from $1,167.00 / night
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
$495.00
from $495.00 / night
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 6 nights min
- Child friendly
- Pet friendly
$710.00
from $710.00 / night
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$763.00
from $763.00 / night
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$982.00
from $982.00 / night
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$982.00
from $982.00 / night
Bell View: Private tennis court and an in-law suite.
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 16 16
- 3 nights min
- Child friendly
$1,694.00
from $1,694.00 / night
Two Beaches: Walk to Long Beach or Good Harbor!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- 6 nights min
- Child friendly
$643.00
from $643.00 / night
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 3 nights min
- Ask about children
- Pet friendly
$668.00
from $668.00 / night
Helena House: European flair, close to Plum Cove Beach.
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Child friendly
- Pet friendly
$563.00
from $563.00 / night
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Air conditioning
$497.00
from $497.00 / night
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$814.00
from $814.00 / night
Plaisance - Enjoy the best of Gloucester living.
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$899.00
from $899.00 / night
Beach Walk: Good Harbor Beach footbridge just steps away!
Gloucester Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 6 nights min
- Ask about children
$294.00
from $294.00 / night
Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
$1,169.00
from $1,169.00 / night
Cedar Ledge Annisquam: Ocean views & traditional New England charm.
Gloucester House
- 6 bedrooms 6
- 2 bathrooms
- sleeps 14 14
- 3 nights min
- Child friendly
- Pet friendly
$1,422.00
from $1,422.00 / night
Terra Nova Cottage
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 6 nights min
- Child friendly
- Air conditioning
$658.00
from $658.00 / night
Chester Square: Waterfront home in historic Annisquam Village.
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
$1,283.00
from $1,283.00 / night
Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
$493.00
from $493.00 / night
The Mount: Walk to Niles Beach & Rocky Neck from this elegant home.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Air conditioning
$739.00
from $739.00 / night
River's Edge: A charming 2BR riverfront home in Gloucester.
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 4 4
- 31 nights min
- Ask about children
$250.00
from $250.00 / night
River Watch: Waterfront rental home with views and private dock.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$571.00
from $571.00 / night
Sea Fox: Custom-designed home with rights to private Coffins Beach
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
- Air conditioning
$991.00
from $991.00 / night
Bray Cottage: A charming cottage close to Wingaersheek Beach.
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
- Pet friendly
$524.00
from $524.00 / night
Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$687.00
from $687.00 / night
Your search has been expanded 12.9 miles to include more rentals
Ocean Front Cottage on Scenic Long Beach
Rockport Cottage - 3.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$516.00
from $516.00 / night
Directly on Long Beach Rockport MA
Rockport House - 3.1 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 14 14
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$687.00
from $687.00 / night
Happy Days Cottage: Charming Folly Cove house with waterfront deck
Rockport Cottage - 5.1 miles away
- 4 bedrooms 4
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Ask about children
- Pet friendly
$550.00
from $550.00 / night
Bearskin Nest: Contemporary living in the heart of coastal charm.
Rockport Apartment - 4.1 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 3 nights min
- Ask about children
$385.00
from $385.00 / night
Clamshell Landing: Bring your game to its squash & tennis courts!
Essex House - 5.3 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 14 14
- 3 nights min
- Ask about children
- Air conditioning
$2,423.00
from $2,423.00 / night
Beach Bungalow: The perfect getaway to two of Rockport's finest beaches!
Rockport Cottage - 3.2 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Child friendly
$493.00
from $493.00 / night
Classic Victorian home with views of the ocean and twin light houses.
Rockport House - 4 miles away
- 7 bedrooms 7
- 2 bathrooms
- sleeps 14 14
- 7 nights min
- Child friendly
$1,091.00
from $1,091.00 / night
Ryal Side Hideaway Cove: A hidden gem with river views in Beverly.
Beverly House - 12.9 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
- Pet friendly
$497.00
from $497.00 / night
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.
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.