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Gloucester Vacation Rentals

Find 661 available offers from 5 partners
Gloucester
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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed & Breakfast
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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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Save up to 72%

Best Vacation Home Deals in Gloucester

Apartment Gloucester
Apr 8 - Apr 15
-72%
$540
$150 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Rockport with Electric Fireplace + House View
5.0
"Excellent" (126 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Jun 1 - Jun 8
-27%
$650
$475 per night
House ∙ 4 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Easy Parking + Incredible Views
5.0
"Excellent" (62 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Feb 10 - Feb 17
-65%
$1,075
$381 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Rockport with Yard & Grill
5.0
"Excellent" (35 ratings)
Gloucester, Essex County, Massachusetts, United States
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Compare and find a vacation rental fitting your expectations among the 661 fantastic properties from different vacation rental websites in Gloucester. The website HomeToGo immediately sorts all of these offers so you can save up to 52%!

Book Vacation Rental Offers with the Highest User Rating

Top-Rated Rentals and Accommodations in Gloucester

Cottage Gloucester
Mar 26 - Apr 2
-51%
$475
$231 per night
Cottage ∙ 8 guests ∙ 4 bedrooms
Cottage in Gloucester with Grill & Yard
5.0
"Excellent" (186 ratings)
Gloucester, Essex County, Massachusetts, United States
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Apartment Gloucester
May 22 - May 29
-21%
$200
$158 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Lovely Apartment in Gloucester with Private Balcony
5.0
"Excellent" (110 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Dec 9 - Dec 16
-52%
$549
$263 per night
House ∙ 12 guests ∙ 4 bedrooms
Nice Vacation Home in Gloucester with Yard & Grill + Water Views + Next to Beach
5.0
"Excellent" (80 ratings)
Gloucester, Essex County, Massachusetts, United States
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Recommended Vacation Rentals in Gloucester

Find your perfect vacation rental in Gloucester: from $117 per night

House Gloucester
May 20 - May 27
-23%
$492
$380 per night
House ∙ 4 guests ∙ 3 bedrooms
House in Rockport with Yard & Grill
4.9
"Excellent" (132 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Sep 23 - Sep 30
-23%
$650
$497 per night
House ∙ 4 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Easy Parking + Incredible Views
5.0
"Excellent" (62 ratings)
Gloucester, Essex County, Massachusetts, United States
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Apartment Gloucester
May 24 - May 31
-21%
$200
$200 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Lovely Apartment in Gloucester with Private Balcony
5.0
"Excellent" (110 ratings)
Gloucester, Essex County, Massachusetts, United States
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Cottage Gloucester
Nov 25 - Dec 2
-18%
$240
$188 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Rockport with Grill & Yard
4.9
"Excellent" (139 ratings)
Gloucester, Essex County, Massachusetts, United States
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Cottage Gloucester
Mar 27 - Apr 3
-43%
$475
$297 per night
Cottage ∙ 8 guests ∙ 4 bedrooms
Cottage in Gloucester with Grill & Yard
5.0
"Excellent" (187 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Mar 16 - Mar 23
$323 per night
House ∙ 6 guests ∙ 4 bedrooms
Beautiful Vacation Home in Gloucester with Pool, Yard & Grill
5.0
"Excellent" (183 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Dec 9 - Dec 16
-52%
$366
$262 per night
House ∙ 12 guests ∙ 4 bedrooms
Nice Vacation Home in Gloucester with Yard & Grill + Water Views + Next to Beach
5.0
"Excellent" (80 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Jun 24 - Jul 1
$300 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Gloucester with Yard & Grill + Harbor View
5.0
"Excellent" (101 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Apr 28 - May 5
$497 per night
House ∙ 12 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Grill
Gloucester, Essex County, Massachusetts, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Gloucester

Cottage Gloucester
Nov 25 - Dec 2
-21%
$240
$189 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Rockport with Grill & Yard
4.9
"Excellent" (140 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
May 20 - May 27
-24%
$495
$379 per night
House ∙ 4 guests ∙ 3 bedrooms
House in Rockport with Yard & Grill
4.9
"Excellent" (132 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Mar 31 - Apr 7
$323 per night
House ∙ 6 guests ∙ 4 bedrooms
Beautiful Vacation Home in Gloucester with Pool, Yard & Grill
5.0
"Excellent" (184 ratings)
Gloucester, Essex County, Massachusetts, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Gloucester and book a vacation rental with air conditioning.

House Air conditioning Gloucester
May 20 - May 27
-23%
$495
$380 per night
House ∙ 4 guests ∙ 3 bedrooms
House in Rockport with Yard & Grill
4.9
"Excellent" (132 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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House Air conditioning Gloucester
Jun 1 - Jun 8
-27%
$650
$475 per night
House ∙ 4 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Easy Parking + Incredible Views
5.0
"Excellent" (62 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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Apartment Air conditioning Gloucester
May 24 - May 31
-21%
$200
$158 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Lovely Apartment in Gloucester with Private Balcony
5.0
"Excellent" (110 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Gloucester accommodation with high-speed internet.

Cottage Internet Gloucester
Nov 25 - Dec 2
-18%
$230
$188 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Rockport with Grill & Yard
4.9
"Excellent" (139 ratings)
Gloucester, Essex County, Massachusetts, United States
Internet
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House Internet Gloucester
Mar 31 - Apr 7
$322 per night
House ∙ 6 guests ∙ 4 bedrooms
Beautiful Vacation Home in Gloucester with Pool, Yard & Grill
5.0
"Excellent" (183 ratings)
Gloucester, Essex County, Massachusetts, United States
Internet
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Cottage Internet Gloucester
Mar 27 - Apr 3
-44%
$473
$267 per night
Cottage ∙ 8 guests ∙ 4 bedrooms
Cottage in Gloucester with Grill & Yard
5.0
"Excellent" (187 ratings)
Gloucester, Essex County, Massachusetts, United States
Internet
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Vacation homes and rentals with a yard

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Gloucester with private yards.

House Yard Gloucester
Apr 7 - Apr 14
-78%
$391
$85 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Grill & Yard
Gloucester, Essex County, Massachusetts, United States
Yard
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House Yard Gloucester
Apr 1 - Apr 8
-40%
$995
$597 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Rockport with Granite Fireplace + Gorgeous Views
5.0
"Excellent" (38 ratings)
Gloucester, Essex County, Massachusetts, United States
Yard
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House Yard Gloucester
Apr 22 - Apr 29
-57%
$796
$344 per night
House ∙ 7 guests ∙ 3 bedrooms
Family Friendly House in Gloucester with Private Parking + Ocean Views
5.0
"Excellent" (31 ratings)
Gloucester, Essex County, Massachusetts, United States
Yard
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Popular Rental Amenities in Gloucester

  • Internet (597)
  • TV (568)
  • Air conditioning (525)
  • No smoking (479)
  • Microwave (438)
  • Kitchen (406)
  • No pets (397)
  • Yard (346)
  • Grill (317)
  • Washer (302)
  • Dishwasher (268)
  • Fireplace (178)

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, 597 accommodations offer "Internet". Consequently, if you need internet access during your vacation, use the Internet filter to compare these rentals. Not as many rentals in Gloucester are available if you want a rental with a pool or if you need a crib for your baby as "Fenced" and "Wheelchair accessible" are not often available in Gloucester.

The Weather in Gloucester

max.
Min.
37°
21°
13 days 13
max.
Min.
37°
21°
15 days 15
max.
Min.
45°
28°
14 days 14
max.
Min.
57°
39°
14 days 14
max.
Min.
68°
48°
14 days 14
max.
Min.
75°
55°
12 days 12
max.
Min.
82°
64°
11 days 11
max.
Min.
81°
63°
9 days 9
max.
Min.
73°
54°
8 days 8
max.
Min.
63°
45°
12 days 12
max.
Min.
50°
34°
10 days 10
max.
Min.
43°
28°
16 days 16
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. In July maximum temperatures go higher than 82°. On the other hand, you could have temperatures dropping under 21° in January. The rainiest month is December while the driest month is September.

7-Day Weather Forecast in Gloucester

Sun, 26 Mar
46°
41°

15%

6 h

18 mi/h

Mon, 27 Mar
46°
35°

0%

8 h

8 mi/h

Tue, 28 Mar
39°
37°

15%

0 h

3 mi/h

Wed, 29 Mar
44°
33°

5%

7 h

16 mi/h

Thu, 30 Mar
37°
32°

15%

0 h

12 mi/h

Fri, 31 Mar
39°
35°

15%

0 h

10 mi/h

Sat, 1 Apr
48°
37°

15%

4 h

15 mi/h

Accommodations for your vacation in Gloucester

Vacationers who are hoping to find house rental 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 164 m² as well as a median price of $648 a night. Furthermore, this category of property is great for large groups, as the majority of house rental can accommodate groups of 7. If you would prefer to book another accommodation type, you could consider apartment rental, which are the second most typical type of accommodation in Gloucester. The average size of apartment rental in Gloucester is 81 m², and the average price is $369 per night.
Where to find the best food in Gloucester?

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.

What are the best places to discover the arts and culture of Gloucester?

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.

What are the best activities for families in Gloucester?

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.

Information about vacation rentals in Gloucester

🏡 Vacation rentals 661 properties
💳 Possible discounts up to 52%
🌙 Nightly prices starting at $85
⭐ Popular amenities Internet, TV and Air conditioning
🐾 Pet friendly accommodations 99 properties
🏊 Vacation rentals with pools 103 properties

Frequently Asked Questions

What is the typical price per night for a vacation rental in Gloucester?

The nightly price of accommodations in Gloucester starts at $85. If you are looking for a house rental, the nightly price is $648 on average. A apartment rental Gloucester will cost $369 per night on average.

How many vacation rentals are available to book in Gloucester?

There are currently 661 vacation homes from 5 different providers in Gloucester.

What are the most popular amenities for vacation rentals in Gloucester?

If you're looking to book a vacation rental in Gloucester, others search for homes with these amenities: TV, Internet and Air conditioning.

How many vacation rentals with pools are there in Gloucester?

Gloucester offers 103 Hotel room and Motel room options on offer to rent.

Are pets allowed in vacation homes in Gloucester?

In case if you are traveling with a pet in Gloucester - 15% of vacation rentals allow pets.

What are the best months to travel to Gloucester?

If choosing a vacation home in Gloucester, consider that rainy season is usually in December or February, with September often being the driest.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Gloucester TripAdvisor Vacation Rentals in Gloucester Vrbo Vacation Rentals in Gloucester VacationRentals.com Vacation Rentals in Gloucester HouseTrip Vacation Rentals in Gloucester FlipKey Vacation Rentals in Gloucester Homestay.com Vacation Rentals in Gloucester Only-apartments Vacation Rentals in Gloucester Interhome Vacation Rentals in Gloucester Novasol Vacation Rentals in Gloucester HomeEscape Vacation Rentals in Gloucester

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