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Gloucester Vacation Rentals

Find 543 available offers from 7 partners
Gloucester
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
House
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
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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Best Vacation Home Deals in Gloucester

Save up to 86%

House Gloucester
Apr 13 - Apr 20
-26%
$475
$353 per night
House ∙ 9 guests ∙ 3 bedrooms
House in Rockport with Yard & Grill
4.9
Outstanding (129 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Feb 3 - Feb 10
-86%
$815
$113 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Gloucester with Grill & Yard
5.0
Outstanding (25 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Dec 9 - Dec 16
-64%
$336
$122 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Free Parking
5.0
Outstanding (6 ratings)
Gloucester, Essex County, Massachusetts, United States
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Compare and find a vacation rental fitting your expectations among the 543 fantastic properties from different vacation rental websites in Gloucester. The website HomeToGo immediately sorts all of these offers so you can save up to 86%!

Top-Rated Rentals and Accommodations in Gloucester

Book Vacation Rental Offers with the Highest User Rating

Apartment Gloucester
Dec 2 - Dec 9
$173 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment in Gloucester with Grill
5.0
Outstanding (54 ratings)
Gloucester, Essex County, Massachusetts, United States
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Apartment Gloucester
Nov 21 - Nov 28
$104 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Nice Apartment in Gloucester with Yard & Grill
4.7
Excellent (45 ratings)
Gloucester, Essex County, Massachusetts, United States
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Cottage Gloucester
Jun 7 - Jun 14
$179 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Cottage in Rockport with Grill
5.0
Outstanding (27 ratings)
Gloucester, Essex County, Massachusetts, United States
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Recommended Vacation Rentals in Gloucester

Find your perfect vacation rental in Gloucester: from $85 per night

Cottage Gloucester
Nov 11 - Nov 18
-45%
$549
$300 per night
Cottage ∙ 8 guests ∙ 4 bedrooms
Cottage in Gloucester with Grill & Yard
5.0
Outstanding (202 ratings)
Gloucester, Essex County, Massachusetts, United States
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Cottage Gloucester
Dec 16 - Dec 23
$179 per night
Cottage ∙ 3 guests ∙ 1 bedroom
Cottage in Rockport with Yard
4.9
Outstanding (56 ratings)
Gloucester, Essex County, Massachusetts, United States
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Apartment Gloucester
May 4 - May 11
-19%
$134
$109 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Rockport + Ocean Views
5.0
Outstanding (6 ratings)
Gloucester, Essex County, Massachusetts, United States
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Cottage Gloucester
Nov 18 - Nov 25
-66%
$524
$180 per night
Cottage ∙ 7 guests ∙ 2 bedrooms
Wonderful Cottage in Rockport with Grill
5.0
Outstanding (3 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Jul 20 - Jul 27
$556 per night
House ∙ 10 guests ∙ 6 bedrooms
House in Gloucester with Grill + Scenic Views
4.9
Outstanding (67 ratings)
Gloucester, Essex County, Massachusetts, United States
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Apartment Gloucester
Mar 23 - Mar 30
$185 per night
Apartment ∙ 5 guests ∙ 1 bedroom
Rental Apartment in Gloucester with Grill & Yard + Water Views
4.9
Outstanding (53 ratings)
Gloucester, Essex County, Massachusetts, United States
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Condo Gloucester
Jan 5 - Jan 12
$220 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Rockport + Ocean Views + Next to Beach
4.9
Outstanding (44 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
May 4 - May 11
-29%
$638
$456 per night
House ∙ 6 guests ∙ 3 bedrooms
Nice Vacation Home in Gloucester with Second Fireplace + Fantastic Views
5.0
Outstanding (1 rating)
Gloucester, Essex County, Massachusetts, United States
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Cottage Gloucester
Jan 13 - Jan 20
-65%
$600
$208 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
Lovely Cottage in Gloucester with Yard & Grill
4.9
Outstanding (34 ratings)
Gloucester, Essex County, Massachusetts, United States
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Budget-friendly Vacation Rentals in Gloucester

Find Fantastic yet Inexpensive Offers

House Gloucester
Apr 20 - Apr 27
$711 per night
House ∙ 16 guests ∙ 8 bedrooms
House in Gloucester with Exterior Patio + Ocean Views + Close to Beach
4.6
Excellent (65 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Oct 14 - Oct 21
-18%
$425
$350 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Gloucester with Grill & Yard + Gorgeous Views
5.0
Outstanding (36 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Jan 13 - Jan 20
$494 per night
House ∙ 12 guests ∙ 5 bedrooms
House in Gloucester with Yard & Grill + Beach Nearby
4.9
Outstanding (64 ratings)
Gloucester, Essex County, Massachusetts, United States
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Vacation rentals with Wi-Fi

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

Apartment  Gloucester
Dec 9 - Dec 16
-18%
$499
$409 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Rockport
5.0
Outstanding (92 ratings)
Gloucester, Essex County, Massachusetts, United States
Internet
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House  Gloucester
Nov 11 - Nov 18
-30%
$422
$297 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Gloucester with Grill & Yard + Marsh Views
4.8
Outstanding (74 ratings)
Gloucester, Essex County, Massachusetts, United States
Internet
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House  Gloucester
Jan 13 - Jan 20
-43%
$473
$270 per night
House ∙ 8 guests ∙ 4 bedrooms
Charming Vacation Home in Gloucester with Ample Parking
4.9
Outstanding (36 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  Gloucester
Nov 3 - Nov 10
$347 per night
House ∙ 9 guests ∙ 4 bedrooms
Beautiful House in Rockport with Grill + Ocean Views
5.0
Outstanding (13 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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Cottage  Gloucester
Aug 3 - Aug 10
$150 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Nice Cottage in Rockport with Yard & Grill + Close to Beach
4.9
Outstanding (86 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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Apartment  Gloucester
Nov 3 - Nov 10
-69%
$511
$161 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Rental Apartment in Gloucester
5.0
Outstanding (6 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Gloucester rental with full kitchen.

Apartment  Gloucester
Dec 9 - Dec 16
$85 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Rockport with Grill & Yard
5.0
Outstanding (9 ratings)
Gloucester, Essex County, Massachusetts, United States
Kitchen
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Apartment  Gloucester
Dec 9 - Dec 16
-42%
$195
$113 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Rockport + Ocean Views
5.0
Outstanding (5 ratings)
Gloucester, Essex County, Massachusetts, United States
Kitchen
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House  Gloucester
Dec 16 - Dec 23
-33%
$826
$558 per night
House ∙ 14 guests ∙ 5 bedrooms
House in Rockport with Yard & Grill + Water Views
4.2
Very good (5 ratings)
Gloucester, Essex County, Massachusetts, United States
Kitchen
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Popular Rental Amenities in Gloucester

  • Pet-friendly (76)
  • Air conditioning (484)
  • Kitchen (345)
  • WiFi (550)
  • Pool (92)
  • Parking (25)
  • TV (508)
  • Washing machine (261)
  • Balcony/patio (175)
  • Microwave (388)
  • No smoking (405)
  • Grill (270)

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, 76 accommodations offer "Pets allowed". Consequently, if you bring your pet everywhere, use the Pets allowed filter to compare these rentals. Not as many rentals in Gloucester are available if you need wheelchair access or if you need a crib for your baby as "Crib" and "Wheelchair accessible" are not often available in Gloucester.

Price and Availability Index in Gloucester

Click on any bar to see price and availability information

Vacation Rental Price Information in Gloucester

This graph displays the average prices for the next twelve months in Gloucester. Gloucester is more expensive in August (8/31 - 9/7), where prices are on average $563 a night. Opt for a getaway in March (3/9 - 3/16) 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 August (8/31 - 9/7). More accommodations are available in a week of October (10/28 - 11/4) as the booking rate is only 34%.

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.
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68°
48°
14 days 14
max.
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75°
55°
12 days 12
max.
Min.
82°
64°
11 days 11
max.
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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

Wed, 27 Sep
60°
53°

0%

11 h

3 mi/h

Thu, 28 Sep
60°
53°

10%

11 h

5 mi/h

Fri, 29 Sep
60°
55°

0%

5 h

5 mi/h

Sat, 30 Sep
60°
57°

0%

6 h

4 mi/h

Sun, 1 Oct
66°
57°

0%

11 h

7 mi/h

Mon, 2 Oct
60°
50°

0%

11 h

5 mi/h

Tue, 3 Oct
59°
55°

10%

7 h

6 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 173 m² as well as a median price of $609 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 77 m², and the average price is $339 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 available 543 homes
💳 Possible discounts up to 86%
🌙 Nightly prices starting at $85
⭐ Popular amenities Pets allowed, Air conditioning and Kitchen
🐾 Pet friendly homes 72 homes
🏊 Vacation rentals with pools 92 homes

Frequently Asked Questions

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

The nightly price of accommodations in Gloucester starts at $85. If you would like to stay in a house rental, the average price is $609 per night. A apartment rental Gloucester will cost on average $339 per night.

How many vacation rentals are available for booking in Gloucester?

There are currently 543 rentals from 7 different providers in Gloucester.

What amenities are most popular for vacation rentals in Gloucester?

Three most popular amenities for home rentals in Gloucester include accommodations that have: Air conditioning, Pets allowed, and Kitchen.

How many vacation homes with pools are in Gloucester?

Check out 92 vacation rentals available in Gloucester.

Are pets allowed in vacation homes in Gloucester?

If traveling with a dog in Gloucester, 13% of vacation rentals are pet-friendly.

When is it better to travel to Gloucester?

Gloucester has its warmest time of year around July and August, with average prices of $85 per night.

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