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Gloucester Vacation Rentals

Find 563 available offers from 7 partners
Gloucester
Anytime
Guests
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+

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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Vacation rentals with Wi-Fi

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

Cottage  Gloucester
Jun 1 - Jun 8
$127 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage in Rockport with Patio + Ocean View

4.7
Excellent (93 ratings)
Gloucester, Essex County, Massachusetts, United States
Internet
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House  Gloucester
May 3 - May 10
-38%
$650
$400 per night
House ∙ 11 guests ∙ 5 bedrooms

Vacation Home in Gloucester with Yard, Grill & Patio + Water Views

5.0
Outstanding (22 ratings)
Gloucester, Essex County, Massachusetts, United States
Internet
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Cottage  Gloucester
Mar 2 - Mar 9
$153 per night
Cottage ∙ 3 guests ∙ 1 bedroom

Cottage in Rockport with Yard & Patio

5.0
Outstanding (66 ratings)
Gloucester, Essex County, Massachusetts, United States
Internet
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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.

Cottage  Gloucester
Mar 2 - Mar 9
$93 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Pleasant Cottage in Gloucester with Yard, Grill & Patio + Ocean Views

4.7
Excellent (24 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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Apartment  Gloucester
Mar 2 - Mar 9
-33%
$200
$135 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Rental Apartment in Gloucester with Yard, Patio & Grill

4.9
Outstanding (84 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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House  Gloucester
May 3 - May 10
$357 per night
House ∙ 9 guests ∙ 3 bedrooms

House in Rockport with Yard, Patio & Grill

4.9
Outstanding (138 ratings)
Gloucester, Essex County, Massachusetts, United States
Air conditioning
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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  Gloucester
Feb 15 - Feb 22
-24%
$358
$271 per night
House ∙ 4 guests ∙ 1 bedroom

House in Gloucester with Free Parking

4.9
Outstanding (69 ratings)
Gloucester, Essex County, Massachusetts, United States
Yard
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House  Gloucester
Nov 16 - Nov 23
$454 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Gloucester with Yard, Grill & Patio

4.9
Outstanding (19 ratings)
Gloucester, Essex County, Massachusetts, United States
Yard
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House  Gloucester
May 4 - May 11
$206 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Gloucester with Patio, Grill & Yard + Marsh Views

4.8
Outstanding (78 ratings)
Gloucester, Essex County, Massachusetts, United States
Yard
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Best Vacation Home Deals in Gloucester

Save up to 72%

House Gloucester
May 25 - Jun 1
-18%
$850
$700 per night
House ∙ 10 guests ∙ 5 bedrooms

Whole Vacation Home in Gloucester with Private Parking + Ocean View

5.0
Outstanding (41 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Mar 2 - Mar 9
-72%
$356
$100 per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in Gloucester with Free Parking

5.0
Outstanding (20 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
May 25 - Jun 1
-34%
$518
$343 per night
House ∙ 5 guests ∙ 3 bedrooms

House in Gloucester with Grill, Patio & Yard

5.0
Outstanding (13 ratings)
Gloucester, Essex County, Massachusetts, United States
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Compare and find a vacation rental fitting your expectations among the 563 fantastic properties from different vacation rental websites in Gloucester. The website HomeToGo immediately sorts all of these offers so you can save up to 22%!

Recommended Vacation Rentals in Gloucester

Find your perfect vacation rental in Gloucester: from $93 per night

Apartment Gloucester
Mar 2 - Mar 9
$105 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Nice Rental Apartment in Gloucester with Yard & Grill

5.0
Outstanding (4 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Sep 21 - Sep 28
$425 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Gloucester with Grill, Yard & Patio + Gorgeous Views

5.0
Outstanding (37 ratings)
Gloucester, Essex County, Massachusetts, United States
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Apartment Gloucester
Nov 9 - Nov 16
$175 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Gloucester with Private Patio + Ocean Views

5.0
Outstanding (115 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
May 4 - May 11
$414 per night
House ∙ 9 guests ∙ 4 bedrooms

Beautiful House in Rockport with Grill & Patio + Ocean Views

5.0
Outstanding (27 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Aug 24 - Aug 31
$315 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Gloucester with Private Parking

5.0
Outstanding (36 ratings)
Gloucester, Essex County, Massachusetts, United States
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Cottage Gloucester
Nov 2 - Nov 9
$180 per night
Cottage ∙ 7 guests ∙ 2 bedrooms

Wonderful Cottage in Rockport with Grill & Patio

5.0
Outstanding (4 ratings)
Gloucester, Essex County, Massachusetts, United States
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Apartment Gloucester
Aug 24 - Aug 31
$103 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Nice Apartment in Gloucester with Yard & Grill

4.8
Outstanding (52 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Mar 2 - Mar 9
$500 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Rockport with Patio, Yard & Grill + Ocean Views + Beach Nearby

4.9
Outstanding (64 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Apr 6 - Apr 13
$256 per night
House ∙ 7 guests ∙ 3 bedrooms

Wonderful Vacation Home in Rockport with Yard, Patio & Grill + Close to Beach

4.9
Outstanding (69 ratings)
Gloucester, Essex County, Massachusetts, United States
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Budget-friendly Vacation Rentals in Gloucester

Find Fantastic yet Inexpensive Offers

House Gloucester
Jun 15 - Jun 22
$151 per night
House ∙ 3 guests ∙ 1 bedroom

Beautiful Vacation Home in Gloucester with Private Parking + Water Views

4.9
Outstanding (86 ratings)
Gloucester, Essex County, Massachusetts, United States
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Cottage Gloucester
May 11 - May 18
$274 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Gloucester with Yard, Grill & Patio

5.0
Outstanding (8 ratings)
Gloucester, Essex County, Massachusetts, United States
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Apartment Gloucester
Apr 27 - May 4
$175 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment in Gloucester with Patio & Grill

5.0
Outstanding (60 ratings)
Gloucester, Essex County, Massachusetts, United States
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Top-Rated Rentals and Accommodations in Gloucester

Book Vacation Rental Offers with the Highest User Rating

House Gloucester
Mar 2 - Mar 9
-21%
$975
$775 per night
House ∙ 15 guests ∙ 6 bedrooms

Vacation Home in Gloucester with Patio, Yard & Grill

4.6
Excellent (60 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Mar 2 - Mar 9
-53%
$425
$200 per night
House ∙ 7 guests ∙ 3 bedrooms

Charming Vacation Home in Gloucester with Grill, Patio & Yard

4.5
Excellent (12 ratings)
Gloucester, Essex County, Massachusetts, United States
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House Gloucester
Mar 2 - Mar 9
$575 per night
House ∙ 12 guests ∙ 5 bedrooms

House in Gloucester with Patio, Yard & Grill + Beach Nearby

4.9
Outstanding (66 ratings)
Gloucester, Essex County, Massachusetts, United States
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Popular Rental Amenities in Gloucester

  • Pet-friendly (91)
  • Air conditioning (561)
  • Kitchen (391)
  • WiFi (609)
  • Pool (108)
  • Parking (25)
  • TV (576)
  • Washing machine (301)
  • Balcony/patio (388)
  • Microwave (433)
  • No smoking (587)
  • Grill (315)

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, 93 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 a wheelchair accessible vacation rental or if you want a rental providing a crib as "Crib" 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

Mon, 26 Feb
46°
42°

0%

6 h

9 mi/h

Tue, 27 Feb
46°
41°

50%

1 h

10 mi/h

Wed, 28 Feb
50°
50°

15%

0 h

25 mi/h

Thu, 29 Feb
32°
30°

15%

5 h

17 mi/h

Fri, 1 Mar
44°
44°

10%

5 h

16 mi/h

Sat, 2 Mar
42°
42°

10%

6 h

4 mi/h

Sun, 3 Mar
42°
42°

0%

6 h

11 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 $638 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 85 m², and the average price is $383 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 563 rentals
💳 Possible discounts up to 22%
🌙 Nightly prices starting at $93
⭐ Popular amenities Pets allowed, Air conditioning and Kitchen
🐾 Pet friendly homes 86 homes
🏊 Vacation rentals with pools 94 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 $93. If you would like to stay in a house rental, the average price is $638 per night. A apartment rental Gloucester will cost on average $383 per night.

How many vacation rentals are available for booking in Gloucester?

There are currently 563 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 94 vacation rentals available in Gloucester.

Are pets allowed in vacation homes in Gloucester?

If traveling with a dog in Gloucester, 15% 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 $93 per night.

Find the perfect Gloucester home to match your style

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