Discover a selection of 500 vacation rentals in Gloucester, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including high chairs for kids and kitchens. Prices start at $130 per night, and houses and cottages are popular options for a stay in Gloucester. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Gloucester
Destination guide

Visit Gloucester, America’s oldest seaport

Gloucester’s combination of beautiful beaches, art, and culture make it one of the most incredible destinations on the East Coast. As the oldest seaport in the U.S.A, there is a rich history to discover, with fascinating attractions such as the historic Beauport and the Sleeper-McCann House, which take you on a fascinating journey through time. When you’ve finished lounging on the beach or indulging in the many activities on offer, there’s a wealth of shops and restaurants to explore, which are never far from Gloucester vacation rentals.

Things to do

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)

Enjoy Gloucester’s fantastic fishing

What better way to get into the spirit of this maritime town than by chartering a private fishing trip for you and your family. Out at sea, you can catch a variety of fish like cod or striped bass, or alternatively, you can fish from the pier and catch flounder. Why not venture beneath the waves to explore the stunning coastal sea life with a scuba diving trip? For those who prefer their feet to be on terra firma, check out the beautiful landscapes of Massachusetts on a hiking or biking trail in Dogwood; just don’t forget your camera.


Gloucester—a great destination, come rain or shine

Summer is the most popular time to book Gloucester vacation rentals, owing to the wonderful weather. Between June and August, temperatures average around 66-72°F—perfect for relaxing on the golden sands of Good Harbor Beach. The shoulder seasons of fall and spring are a good time to visit too, with mild weather that’s ideal for exploring the great outdoors. If you plan to spend most of your time indoors, the less crowded winter season might be your best bet. Temperatures drop as low as 18°F, though, so you’ll need to pack warm clothes!

Natural features

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)
How to get there

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.

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.

Explore destinations around Gloucester