Gloucester Vacation Rentals

Our Favorite Vacation Rentals in Gloucester

  • Serenity
     Country House
    Booking.com
    From
    $159
  • Waterfront 2 Bedroom !
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $352
  • Vintage Rockport Escape
     Country House
    Booking.com
    From
    $131
  • Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean
     3br Home/Apartment
    HolidayLettings
    From
    $310
  • Annetti's Watch
     Country House
    Booking.com
    From
    $314
  • Close to Half Moon Bay
    ExcellentHome/Apartment
    HolidayLettings
    From
    $211
  • Manchester by the sea
     Family Stay
    Booking.com
    From
    $100
  • Good Harbor Beach House - Walk to Shops
     3br Home/Apartment
    HolidayLettings
    From
    $230

Check prices for these upcoming dates

Gloucester Vacation Rentals with Wi-Fi

  • Fishnet Cottage
    ExcellentCottage
    Airbnb
    From
    $119
  • Prime location to Beauport Hotel & Beach, Glo Apt
    Excellent2br Home/Apartment
    Airbnb
    From
    $226
  • Gloucester getaway ocean escape
    Good3br Home/Apartment
    Airbnb
    From
    $226
  • Airy Beach Studio
    ExcellentHome/Apartment
    Airbnb
    From
    $167

Gloucester Pet-Friendly Vacation Rentals

  • One Bedroom Loft Apartment B at Cedar Hill Farm B & B
    ExcellentHome/Apartment
    HolidayLettings
    From
    $220
  • Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown
     3br Home/Apartment
    HolidayLettings
    From
    $255
  • Stunning classic family home that has central AC & Outdoor patio W/ kitchen & TV
     4br Home/Apartment
    HolidayLettings
    From
    $297
  • Hotel Quality & Cozy, Near R128 & Trains, Sleeps 6
    Excellent2br Home/Apartment
    Airbnb
    From
    $137

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
64°
3
69°
3
76° 22°
6
86° 34°
3
84° 45°
5
95° 53°
4
92° 47°
3
89° 37°
1
78° 33°
6
71° 16°
4
61°
7
59°
3
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Gloucester. The hottest month in Gloucester is June, when temperatures peak at 95 ˚F. The coolest month is December, when temperatures drop to 2 ˚F. The wettest month in Gloucester is January with 6.6 inches of rain, while the driest month is April with 1.32 inches of rain.

What Expert Travelers Think

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    Whitney WearTravel Better Guide
  • — 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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