Gloucester Vacation Rentals

Compare 697 available properties from 17 providers
Gloucester
Save up to 29%

Best Vacation Home Deals in Gloucester

-29%
e.g. 11/24 - 12/1
House ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $125 $178
HomeAway
4.9
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-17%
e.g. 9/15 - 9/22
House ∙ 4 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $246 $296
VRBO
4.3
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-22%
e.g. 10/27 - 11/3
Apartment ∙ 4 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $250 $321
HomeAway
4.9
View deal

Compare and find a vacation rental fitting your expectations among the 697 fantastic properties from different vacation rental websites in Gloucester. The website HomeToGo immediately sorts all of these offers so you can save up to 29%!

Recommended Vacation Rentals in Gloucester

Rent a vacation accommodation in Gloucester: from $74 per night

Apartment ∙ 2 guests
Gloucester, Essex County, Massachusetts, United States
from $165
VRBO
5.0
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House ∙ 4 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $204
HomeAway
4.8
View deal
House ∙ 4 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $246
VRBO
4.3
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House ∙ 6 guests ∙ 3 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $280
VRBO
5.0
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House ∙ 4 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $240
VRBO
5.0
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $205
VRBO
4.8
View deal
House ∙ 7 guests ∙ 3 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $379
VRBO
4.5
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House ∙ 6 guests ∙ 3 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $263
HomeAway
4.5
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Vacation Homes With Fishing Spots Nearby

Fishing
Private room ∙ 4 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $174
VRBO
4.8
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Fishing
House ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $125
HomeAway
5.0
View deal
Fishing
House ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $125
HomeAway
4.9
View deal
Fishing
Apartment ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $158
HomeAway
4.9
View deal
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Vacation Rentals With a Fireplace

Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $312
HomeAway
5.0
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Fireplace
Apartment ∙ 8 guests ∙ 3 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $390
VRBO
4.2
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Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $415
HomeAway
4.7
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $305
Wimdu
5.0
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Apartments With a Balcony or Patio

Balcony/Patio
House ∙ 5 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $261
HomeAway
5.0
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Balcony/Patio
Apartment ∙ 4 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $250
HomeAway
4.9
View deal
Balcony/Patio
Apartment ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts, United States
from $92
VRBO
4.8
View deal
Balcony/Patio
Apartment ∙ 3 guests ∙ 2 bedrooms
Gloucester, Essex County, Massachusetts, United States
from $94
Wimdu
5.0
View deal
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Popular Rental Amenities in Gloucester

  • Internet (550)
  • TV (530)
  • Parking (506)
  • Kitchen (495)
  • No smoking (477)
  • Microwave (448)
  • AC (411)
  • Grill (389)
  • Washer (368)
  • Dishwasher (315)
  • No pets (304)
  • Fishing (281)
Accommodations can be narrowed down based on various criteria. Above, you will find the number of rentals that provide a specific feature in Gloucester. In Gloucester, 490 accommodations offer "internet". Consequently, if you can't imagine a vacation without internet, use the internet filter to compare these rentals. Not as many rentals in Gloucester are available if you're dreaming of days spent poolside or if you enjoy soaking in the hot tub as "Jacuzzis" and "pools" are not often available in Gloucester.

Price and Availability Index Gloucester

Vacation Rental Price Information in Gloucester

This graph displays the average prices for the next twelve months in Gloucester. Gloucester is more expensive in July (7/21 - 7/28), where prices are on average $384 a night. Opt for a getaway in November (11/17 - 11/24) for optimal savings when heading to Gloucester.

Rental Availability Information in Gloucester

Check how busy Gloucester is with our availability graph. The most challenging week to find a rental in the next twelve months is in July (7/21 - 7/28). More accommodations are available in a week of June (6/15 - 6/22) as the booking rate is only 22%.

The Weather in Gloucester

37°
21°
37°
21°
45°
28°
57°
39°
68°
48°
75°
55°
82°
64°
81°
63°
73°
54°
63°
45°
50°
34°
43°
28°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above are the weather conditions for Gloucester. During July, maximum temperatures go up to more than 82° January is the coolest month, with average minimal temperature reaching 21°. December is the wettest month.

Vacationers who are hoping to find house rentals in Gloucester will have a lot of choices, as they are the most typical vacation accommodation type in this destination. In addition, these accommodations have a median size of 2,300 ft² as well as a median price of $432 a night. Furthermore, this category of property is great for large groups, as the majority of house rentals can accommodate groups of 7. If you would prefer to book another accommodation type, you could consider apartment rentals, which are the second most typical type of accommodation in Gloucester. The average size of apartment rentals in Gloucester is 880 ft², and the average price is $220 per night.

Enjoy a thrilling North Shore trip with a Gloucester vacation rental

Gloucester is one of the oldest English settlements in the United States, and it offers a wealth of experiences for travelers to dig into. Start with a vacation rental near Wingaersheek Beach and wake up to a beautiful morning on the beach every day of your stay. Or try a 4-bedroom colonial house set in a quiet location with a private yard and easy access to the water.

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Food & Drinks

Delight your palate

If you want to enjoy large portions of Italian-inspired pasta, meat entrées, and seafood, the Causeway Restaurant is the place to go, or you can opt to join locals at the Gloucester House Restaurant, serving locally caught seafood in a historic spot. Get your freshly prepared burger or pizza plus other surf 'n' turf menu options at Seaport Grille, which also offers signature drinks to accompany your hearty meal.

Art & Culture

Museums & local history

Take a tour of the Hammond Castle to enjoy its medieval design, or visit Beauport, the Sleeper-McCann House, for a tour through the lovingly furnished home of Henry Sleeper, a trailblazer of interior design. For fine art & maritime collections and a library about Cape Ann, stop at Cape Ann Museum, which also highlights the history of Gloucester as a fishing and trading spot.

Family Activities

Appreciate the wonderful outdoors

Start your day at Stage Fort Park, which features two beautiful beaches, a dog park, baseball fields, picnic benches, a large playground and plenty of space for gatherings. Ravenswood Park is another relaxing spot to explore miles of trails, old carriage roads, and hemlock groves.

When it gets hot, head to the Good Harbor Beach to enjoy a swim in the pristine water. From this serene New England beach, you can even walk out to an island at low tide. Meanwhile, Wingaersheek Beach is an excellent spot for the whole family to relax while the kids wade in the shallow water and explore rock formations.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Gloucester VRBO Vacation Rentals in Gloucester HomeAway Vacation Rentals in Gloucester TripAdvisor Vacation Rentals in Gloucester VacationRentals.com Vacation Rentals in Gloucester HouseTrip Vacation Rentals in Gloucester FlipKey Vacation Rentals in Gloucester Wimdu Vacation Rentals in Gloucester 9flats.com Vacation Rentals in Gloucester VaycayHero Vacation Rentals in Gloucester PerfectPlaces.com Vacation Rentals in Gloucester Homestay.com Vacation Rentals in Gloucester only-apartments Vacation Rentals in Gloucester Interhome Vacation Rentals in Gloucester Bedycasa Vacation Rentals in Gloucester Novasol Vacation Rentals in Gloucester HomeEscape Vacation Rentals in Gloucester

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