Discover a selection of 497 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 swimming pools and air conditioning. Prices start at $105 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)
  • Sagamore Spring Golf Club (19.5 mi / 31.4 km)
  • Maritime Gloucester (0.2 mi / 0.4 km)
  • Appleton Farms Grass Rides (11.1 mi / 17.9 km)
  • Stowaway Sweets (13 mi / 21 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)
  • Front Beach (3.9 mi / 6.3 km)
How to get there

Traveling to and around Gloucester

The nearest airport is in Logan International Airport (BOS), located 24.8 mi (39.9 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 25.4 mi (40.9 km) away.

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

What are the top vacation rentals in or near Gloucester?

The heart wants what the heart wants, and right now that's a vacation. It's time to pack your bags and head for one of these top vacation rentals in or near Gloucester:

  • Make use of conveniences like an iron and ironing board and a barbecue grill at "Oceanfront Contemporary Home - Breathtaking Views". Located around 60 miles from Gloucester, this quality property has 3 bedrooms and good guest reviews.
  • Another great option is "Near Boston Historic Two - Bedroom With Modern Amenities", which is around 25 miles from Gloucester. Offering 2 bedrooms, a playground and a hair dryer, it has everything you need to keep you happy and comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Gloucester vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Gloucester?

Clock off on Friday and then forget about your worries. If you're craving some fun and relaxation, these properties in and around Gloucester promise an unforgettable weekend getaway:

  • Located 4 miles to the northeast of the center of Gloucester, "Periwinkle Cottage #1 - Open All Year" is a good match for adventurous types and nature lovers. Get out and explore nearby attractions, such as Winthrop Shore Reservation and Norman B. Leventhal Park. If you still have time, try some basketball or mountain biking.
  • Alternatively, find your home away from home at "Goosebump Views On The Beach Giant Decks Seen On Hgtv Xtra Clean Chefs Kitchen". Use it as a base to unwind, or be adventurous and try sledding and horse riding. When it's time to discover more of the area, check out Odiorne Point State Park and Back Beach. This sought-after vacation rental is around 19 miles northwest of Gloucester.

Can I find studio apartments for rent in and around Gloucester?

Studio apartments are hard to match when it comes to location, convenience and character. Get comfy in one of these studio apartments for rent in or near Gloucester and get a taste of the local culture and vibe:

  • Make "Historic Home At Freedom Trail" your home away from home. This top property comes with amenities including a nearby laundromat and a living room.
  • Another great option is "Periwinkle Cottage #1 - Open All Year". Make the most of a living room, nearby birdwatching activities and other convenient amenities during your getaway.

There are many attractions around Gloucester to put on your itinerary. Nourish your inner culture vulture by visiting Coolidge Corner Theatre and Busch Reisinger Museum.

Can I find short term rentals in or near Gloucester?

Just because you only have two or three days up your sleeve doesn't mean you have to spend it in a characterless hotel room. Go on vacation but still have the home comforts you love at one of these short-term rentals in or around Gloucester:

  • Nice and close to the heart of Gloucester, "Goosebump Views On The Beach Giant Decks Seen On Hgtv Xtra Clean Chefs Kitchen" is an ideal base for a mini break. While you're in the area, don't miss top sights like Walden Pond and Louisa May Alcott's Orchard House.
  • Leap out of bed, whip up some breakfast and then start planning what to explore around "Best Patio On Commercial" Steps To Everything Exclusive Tropical Gated Gardens". Old Manse and Concord Visitors Center should be on your radar if you choose to stay at this short-term vacation rental.

What are the best romantic weekend getaways in or near Gloucester?

Whether spent in a cabin, an apartment or a lodge, a romantic weekend getaway is an excellent way to add some fire to your relationship. Whisk your special someone away for a couple of leisurely days at one of these enticing escapes in or near Gloucester:

  • Put on some soft tunes and slow dance the nights away at "Near Boston Historic Two - Bedroom With Modern Amenities". Around 25 miles from Gloucester, this property has everything you could want for a romantic weekend away, including air conditioning and a dining table.
  • "Historic Home At Freedom Trail" is another wonderful option that'll impress. It's around 25 miles from Gloucester and comes with beauty services and a restaurant dining guide.

Are there mansions for rent in or near Gloucester?

We've got some lavish mansions for rent in and near Gloucester. If you want somewhere with lots of room as well as that extra wow factor, these architectural stunners will not disappoint:

  • Character, charm and style — "Historic Oceanfront Mansion" has it all in abundance. Around 19 miles northwest of Gloucester and offering a fireplace and a beach view, this lovely place is hard to beat.
  • With a fireplace, golf and lots of other awesome amenities, "Historic Brick Federal Period Mansion On Fabled Chestnut Street" will get your team's tick of approval. This opulent home is around 14 miles to the southwest of Gloucester.

What are the best large group vacation rentals in or near Gloucester?

Big groups mean big-time fun. They also mean finding a place that'll effortlessly fit your entire crew. Check out our large group vacation rentals in or around Gloucester and get your loved ones together under the one roof:

  • There's loads of space to spread out at "Stunning Views From Beachfront House In Manchester". Around 4 miles southwest of Gloucester, this welcoming retreat has 5 bedrooms that sleep up to 12 guests. Top amenities include a kitchen and a beach view.
  • Invite up to 12 of your dearest friends to "Elegant And Expansive Victorian Home" and fill its spaces with laughter and love. This option has 6 bedrooms and is around 4 miles to the north of Gloucester. It's crammed with features to keep your group happy and comfortable, including a beach view and an ocean view.

What are the best houses for rent with a pool in or near Gloucester?

Nothing says fun times like a pool does. Grab your inflatable flamingo and check out these rental houses in or near Gloucester that come with this vacation must-have:

  • Treat the gang to a memorable stay at "4 Bedroom Lux House/with Pool Next Door". There's a lot to love about this getaway besides its pool, such as coffee and tea making facilities and a barbecue grill.
  • "Good Harbor Beach House" is the type of place you go to escape the everyday and enjoy your surroundings, starting with its awesome pool. Nearby whale-watching activities and coffee and tea making facilities are also on hand to make your visit nice and comfy.

Gloucester has a humid continental climate, with average summertime temperatures fluctuating between 65 ºF and 70 ºF. But you don't have to wait until summer to visit. Check out the search bar at the top of the page and adjust the filters to find the perfect Gloucester vacation rental and plan your escape for whenever you like.

What are the best large family vacation rentals in or near Gloucester?

No matter if your idea of the perfect escape is out in the countryside or down by the sea, you'll have a lot more fun if you share it with loved ones. Stay in one of these large family vacation rentals in or near Gloucester and bring the entire crew along:

  • Get your nearest and dearest together at "Goosebump Views On The Beach Giant Decks Seen On Hgtv Xtra Clean Chefs Kitchen", which has 3 bedrooms that sleep up to 8 guests. This getaway is located 19 miles to the northwest of Gloucester and comes with amenities such as nearby ecotour services and a TV.
  • Another great choice is "Good Harbor Beach House". This vacation rental is 2 miles northeast of Gloucester and features a DVD player, towels and more. With 4 bedrooms accommodating up to 8 people, you won't have to leave anyone off your guest list.

If you're looking for family-friendly attractions in the area, you're spoiled for choice. New England Aquarium, Newbury Street and CoCo Key Water Resort - Boston offer fun for all ages.

What are the best large houses to rent with indoor pools in or near Gloucester?

Nothing says "VIP getaway" like having an indoor pool. Pack your bikini and go for a dip in the privacy of one of these large vacation homes in or near Gloucester:

  • With 4 bedrooms that can sleep up to 14 guests, "Beach, Pool, Housekeeping And More Inquire First For Best Rate" is the perfect place to take a break with the people that matter most. Take advantage of this property's host of amenities, such as a swimming pool and a sauna.
  • Besides its awesome indoor pool, "Beach, Pool, Housekeeping And More Inquire First For Best Rate" comes with an ocean view and a water view. It has 4 bedrooms that can accommodate up to 14 people, so you can bring the whole crew along.

Want to see more options? Find your dream pad by using the search bar at the top of the page. Simply adjust the filters to find the Gloucester vacation rental that's perfect for you.

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