Gloucester vacation rentals

We found 597 vacation rentals — enter your dates for availability

your current months are October, 2023 and November, 2023.
October 2023
SSundayMMondayTTuesdayWWednesdayTThursdayFFridaySSaturday
1
November 2023
SSundayMMondayTTuesdayWWednesdayTThursdayFFridaySSaturday
Discover a selection of 133 homes, 37 apartments, and other vacation rentals in Gloucester that are perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, such as WiFi and a pool. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

Houses

Houses
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

The historic area of Gloucester awaits your stay

Come and experience Gloucester and its monuments, history and art galleries. This city's seaside, beaches and whale watching draw many visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Gloucester

Are you searching for things to do in the city? Venture out of your cozy vacation rental and experience everything that Gloucester has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Salem Willows Park (11.8 mi / 19 km)
  • Bewitched in Salem (13.2 mi / 21.2 km)
  • CoCo Key Water Resort - Boston (15.6 mi / 25.2 km)
  • Appleton Farms Grass Rides (11.1 mi / 17.9 km)
  • Witch Mansion (13.3 mi / 21.4 km)
  • Mill River Winery (14.5 mi / 23.4 km)

Exploring the natural features in Gloucester

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Gloucester is a great spot to appreciate mother nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Half Moon Beach (0.9 mi / 1.4 km)
  • Stage Fort Park (0.9 mi / 1.4 km)
  • Good Harbor Beach (1.7 mi / 2.8 km)
  • Long Beach (2.7 mi / 4.3 km)
  • Wingaersheek Beach (2.9 mi / 4.7 km)
  • Pebble Beach (3.5 mi / 5.7 km)

Seasonal weather averages in Gloucester

If you're planning a vacation around the weather, August, July, September and June are the hottest months to visit, when temperatures average 68°F.

Traveling to and around Gloucester

The nearest airport is in Beverly, MA (BVY-Beverly Municipal), located 12.8 mi (20.6 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Lawrence, MA (LWM-Lawrence Municipal), which is 24.3 mi (39.1 km) away.

If you prefer train travel, make your way to Gloucester Station or West Gloucester Station to see more of the city.

Frequently asked questions

What is the best area to stay in Gloucester when booking a vacation rental?

If you're planning a vacation in Gloucester, Annisquam is among the most in-demand locations to stay. No matter your style of travel, Vrbo is sure to have a vacation property here that has everything you need.

How many vacation rentals are in Gloucester?

Our current selection of vacation rentals in Gloucester is ${propertiesCount}. It just takes a quick Vrbo property search to securely book your next house, condo, cabin or whatever kind of vacation home that suits you.

What is the most popular type of vacation rental accommodation in Gloucester?

Based on our data, houses are considered the most popular vacation rental type in Gloucester. But naturally, everyone's idea of the perfect trip isn't going to be the same. Vrbo has vacation homes of all shapes and sizes, and we'll help you to find your ideal fit.

How much does it cost to rent a vacation rental in Gloucester?

A range of things can determine how much you'll pay for a vacation rental in Gloucester, such as the season, length of stay and type of property. Still, all Vrbo homes have something in common — incredible value. Just add your travel dates to find your ideal escape.

How much does it cost to rent a beach house in Gloucester?

The average price for a vacation rental by the beach in Gloucester will depend on when you'll be there and the type and size of property you want. You can find prices quickly and easily on Vrbo by entering your travel dates. Then use the filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a pool.

Are there pet-friendly vacation rentals in Gloucester?

Happily, yes. You'll have a choice of 74 vacation rentals that welcome pets in Gloucester on Vrbo. Our cuddly best friends need a break too, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where your pooch can lap up the good times.

Can I rent a house with a pool in Gloucester?

Add another level of fun to your adventure by booking your group into one of the two houses with a private pool in Gloucester. Use our handy search filter to find the kind of property you want on Vrbo, and then spend your downtime splashing around in a swimming pool that's only for you.

What are popular rental amenities in Gloucester?

A nearby waterfront, an ocean view and a fireplace are the most popular rental amenities in Gloucester. Whether you plan to travel alone, with your spouse or a group of family members, Vrbo can help you find a vacation home that matches your tastes with all the features you'll enjoy.

Are there large group vacation rentals in Gloucester?

Gloucester has 13 vacation properties that can cater to 10 or more people. These stays come with the space you need to enjoy good times with family and friends.

Are there vacation rentals in Gloucester that welcome kids?

Bring the entire family together for fun-filled adventures in Gloucester at one of our 74 family-friendly vacation homes. Lots of these stays provide conveniences that are suitable for trips with the kids, like full kitchens, multiple bedrooms and entertainment units. Simply check the "Properties good for families" filter and choose your favorite option.

What are the top attractions for families in Gloucester?

Keep the kids amused at these fun family-friendly attractions in Gloucester:

  • Hammond Castle
  • Capt Bill & Sons Whale Watch
  • Maritime Gloucester

Are there one-bedroom vacation rentals in Gloucester?

Yes, you can take your pick from 11 one-bedroom rentals in Gloucester. Whether you're searching for a comfy cottage or a condo, our one-bedroom rentals are ideal if you don't need lots of room. One of the best parts about having your own pad? You won't ever have to share your adventure with strangers.

Explore destinations around Gloucester