Gloucester Vacation Rentals

See all 649 deals in Gloucester

Our Favorite Vacation Rentals in Gloucester

  • Good Harbor Haven
     Country House
    Booking.com
    From
    $171
  • Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown
     3br Home/Apartment
    HolidayLettings
    From
    $307
  • Annetti's Watch
     Country House
    Booking.com
    From
    $337
  • Charming 2 bedroom Rockport Carriage House
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $366
  • Vintage Rockport Escape
    ExcellentCountry House
    Booking.com
    From
    $150
  • Loft Apartment A at Cedar Hill Farm B&B
     Home/Apartment
    HolidayLettings
    From
    $220
  • Olde New House
     Home/Apartment
    Booking.com
    From
    $132
  • Charming cottage near the ocean w/beach access & near Gloucester!
     2br Cottage
    HolidayLettings
    From
    $317

Check prices for these upcoming dates

Gloucester Vacation Rentals with Wi-Fi

  • Fishnet Cottage
    ExcellentCottage
    Airbnb
    From
    $153
  • Walk to Good Harbor Beach
    ExcellentHome/Apartment
    Airbnb
    From
    $198
  • Stunning Penthouse Apartment overlooking the sea!
    ExcellentHome/Apartment
    Airbnb
    From
    $333
  • Gloucester getaway ocean escape
    Good3br Home/Apartment
    Airbnb
    From
    $226

Gloucester Pet-Friendly Vacation Rentals

  • Dog-friendly apartment in a prime location - walk to town beaches!
     Home/Apartment
    HolidayLettings
    From
    $240
  • The Little Red House with Prize Ocean View
     2br Home/Apartment
    HolidayLettings
    From
    $183
  • Wingaersheek Beach House (Private)
    Excellent6br Home/Apartment
    Airbnb
    From
    $2,189
  • New Listing - Summer Retreat in the Trees
    Excellent2br Home/Apartment
    Airbnb
    From
    $311

Gloucester Travel Guide

Gloucester is the oldest seaport in the United States and it has also become a summer vacation destination for family fun. As part of the Massachusetts’ North Shore, this city boasts lots of stunning beaches and a picturesque harbor, with lots of opportunity for boating, swimming, and fishing. The Main Street in Gloucester is home to boutiques and local stores, as well as restaurants to enjoy in the evening. In particular, waterfront dining is popular, with beautiful views of the harbor with a fine dining experience. Local and fresh seafood is always top of the menu in Gloucester.

Things to Do in Gloucester

Gloucester is home to some fantastic beaches to explore. This includes Wingaersheek Beach, which is a popular place to paddle and go beachcombing. The water is clean and the sand is pristine. Good Harbor Beach is another favorite spot for locals and visitors alike, with beautiful white sand and blue sea. This is where to go when the sun is shining. For stunning harbor views, head to Stage Fort Park and Beach. To view a historic home in Gloucester, head to the Sleeper-McCann House. This is a stunning mansion and visitors can tour the rooms of this designer. The Cape Ann Museum is also a place to learn about the area’s past and the roles of fishing and shipping in town.

Best Time to Visit Gloucester

The summer is the most popular time to vacation in Gloucester.

Price and Availability in Gloucester

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Gloucester tends to be Sunday, while the most expensive day tends to be Thursday. Vacation homes in Gloucester tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Gloucester is in August, while the cheapest month is in April. The most popular time to book a vacation rental in Gloucester is in the high season in August. Gloucester has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Gloucester

Rainy days
93 º45
6
83 º25
5
69 º12
10
62 º15
3
62 º-4
2
76 º7
4
62 º13
5
69 º24
5
89 º37
2
88 º48
3
96 º52
3
94 º53
5
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Gloucester. The hottest month in Gloucester is June, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to -4 ˚F. The wettest month in Gloucester is February with 10.2 inches of rain, while the driest month is August with 1.73 inches of rain.

What Expert Travelers Think

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  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
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  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
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