Gloucester Vacation Rentals

Our Favorite Vacation Rentals in Gloucester

  • Vintage Rockport Escape
     Country House
    Booking.com
    From
    $172
  • Waterfront 2 Bedroom !
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $352
  • Manchester by the sea
     Family Stay
    Booking.com
    From
    $100
  • Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean
     3br Home/Apartment
    HolidayLettings
    From
    $498
  • Cottage near the Sea
     Country House
    Booking.com
    From
    $294
  • Close to Half Moon Bay
    ExcellentHome/Apartment
    HolidayLettings
    From
    $205
  • Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet
    ExcellentCottage
    HolidayLettings
    From
    $195
  • Loft Apartment A at Cedar Hill Farm B&B
     Home/Apartment
    HolidayLettings
    From
    $220

Check prices for these upcoming dates

Gloucester Vacation Rentals with Wi-Fi

  • Fishnet Cottage
    ExcellentCottage
    Airbnb
    From
    $131
  • Downtown Gloucester Condominium
    Excellent2br Home/Apartment
    Airbnb
    From
    $283
  • Gloucester getaway ocean escape
    Good3br Home/Apartment
    Airbnb
    From
    $226
  • Airy Beach Studio
    ExcellentHome/Apartment
    Airbnb
    From
    $167

Gloucester Pet-Friendly Vacation Rentals

  • Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown
     3br Home/Apartment
    HolidayLettings
    From
    $324
  • Wingaersheek Beach House (Private)
    Excellent6br Home/Apartment
    Airbnb
    From
    $2,189
  • Beverly Farms Lovely Immaculate Home Best Location
    Good4br Home/Apartment
    Airbnb
    From
    $1,836
  • Walk to Good Harbor Beach
    ExcellentHome/Apartment
    Airbnb
    From
    $198

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
69° 12°
10
62° 15°
3
62° -4°
2
76°
4
62° 13°
5
69° 24°
5
89° 37°
2
88° 48°
3
96° 52°
3
94° 53°
5
93° 45°
6
83° 25°
5
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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

  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

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