Gloucester, MA is a city packed with history dating back 400 years. Visitors can explore lighthouses, museums and the beaches. If you're planning a vacation to Gloucester, read through these suggestions for a fun-filled trip.

Top vacation rentals in Gloucester

Entrance to Good Harbor Beach just down the street!
5.0
Outstanding(167 Reviews)
Cottage
 in Gloucester
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
8 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

Discover the beauty of Gloucester with a stay at Good Harbor Beach House - walk to beach, close to restaurants and shopping!, a top rated Cottage with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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View from a bench on the property overlooking the harbor.
4.8
Outstanding(248 Reviews)
Condo
 in Gloucester
Prime Gloucester Property Overlooking Inner Harbor
6 guests · 2 bedrooms · 2 baths
Garden · Pool · Pets allowed

Indulge in a peaceful retreat at Prime Gloucester Property Overlooking Inner Harbor, our elegant Condo in Gloucester. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
3.5
Average(571 Reviews)
Motel
 in Gloucester
Captain's Lodge Motel
Pool · Kitchen / Kitchenette · Air conditioner

This Motel for $345 in Gloucester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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4.8
Outstanding(124 Reviews)
Bed and Breakfast
 in Rockport
Seafarer Inn
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Nestled in Gloucester, this Bed and Breakfast is perfect for your next vacation. Enjoy Seafarer Inn's top-rated amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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Vacation rentals with internet & wifi in Gloucester

Shari Blaukopf Canadian artist's rendition of the infamous Motif #1.
5.0
Outstanding(155 Reviews)
Condo
 in Rockport
'We can't wait to return to Four Winds'
4 guests · 2 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Gloucester, at $394 per night for your next great vacation.

$$$$
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Ocean view from apartment
5.0
Outstanding(146 Reviews)
Condo
 in Rockport
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
4 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Indulge in a peaceful retreat at Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE), our elegant Condo in Gloucester. Enjoy amenities including Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.

$$$$
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4.1
Excellent(960 Reviews)
Hotel
 in Rockport
3star
Rockport Inn and Suites
Pool · Pets allowed · Kitchen / Kitchenette

Indulge in a peaceful retreat at Rockport Inn and Suites, our elegant Hotel in Gloucester. Enjoy amenities including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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4.5
Excellent(161 Reviews)
Inn
 in Gloucester
Harborview Inn
Garden · Kitchen / Kitchenette · Air conditioner

This Inn in Gloucester, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Gloucester

Gloucester travel guide

Let us help you plan your perfect Gloucester vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Gloucester, and more.

Frequently asked questions

What is the price range for rentals in Gloucester?

Vacation rentals in Gloucester have a price range between $70-$1,571. The average price for rentals in Gloucester is $294 per night.

What do I need to know before visiting Gloucester, MA?

Before visiting Gloucester, MA, it is important to know a few things.

  • It is a popular beach town located on the North Shore of Massachusetts.
  • The town is home to several museums, galleries, restaurants, and shops.
  • It is also known for its fishing industry, art colony, and historic sites.

Visitors should also be prepared for the area's unpredictable weather, and be sure to bring appropriate clothing and footwear.

What are the top things to do in Gloucester, MA?

Gloucester, MA is a beautiful and historic city, located on the Atlantic Coast. There are many fun and interesting things to do in Gloucester, MA. Here are some of the top activities:

  • Visit the Rocky Neck Art Colony
  • Take a whale watching cruise
  • Explore the Cape Ann Museum
  • Hike the Halibut Point State Park
Gloucester is a great destination for outdoor enthusiasts, art lovers, and history buffs alike. Whether you're looking for a relaxing day outdoors or a fun, educational experience, Gloucester, MA has something to offer for everyone.

Where is Gloucester, MA?

Gloucester, MA is a historic fishing port located on the North Shore of Massachusetts, about 30 miles northeast of Boston. It is known for its rocky shoreline, historic architecture, and art galleries. Gloucester is also home to the famous Fisherman's Memorial, a tribute to the fishermen who have lost their lives at sea.

What are the popular shopping destinations in Gloucester, MA?

Gloucester, MA is a great destination for shopping. Here are some popular spots to check out:

  • Cape Ann Marketplace
  • Stage Fort Park
  • Gloucester Marine Railways

Is Gloucester, MA safe to travel to?

Gloucester, MA is generally safe to travel to. Here are some tips to keep in mind when visiting:

  • Be aware of your surroundings
  • Avoid walking alone at night
  • Be cautious of unfamiliar people

By following these safety tips, you can ensure a safe and enjoyable trip to Gloucester, MA.

What is the culture like in Gloucester, MA?

Gloucester, MA is a coastal city located in northeastern Massachusetts. It has a unique culture that is heavily influenced by its location on the coast and its rich history as a fishing port. Here are five key points that depict the culture of Gloucester:

  • The city is well-known for its seafood industry, with fishing being a major part of Gloucester’s economy and culture.
  • The city is home to several art galleries, museums, and festivals that celebrate the heritage of the city.
  • The city’s economy is heavily reliant on tourism, with many tourists visiting in the summer months for its sandy beaches and maritime activities.
  • The city is known for its close-knit community and friendly atmosphere.
  • Gloucester is home to many historic sites, such as the Eastern Point Lighthouse and Hammond Castle.

Where can I find affordable accommodation in Gloucester, MA?

Gloucester, MA has a variety of affordable accommodation options to choose from. Here are some of the top recommended choices:

  • Beauport Hotel Gloucester
  • Cape Ann's Marina Resort
  • Stage Fort Park Cabins
  • Essex River House Inn

Beauport Hotel Gloucester offers comfortable accommodations with amenities including a swimming pool and fitness center. Cape Ann's Marina Resort features modern rooms and a variety of boat slips for guests to enjoy. Stage Fort Park Cabins provides rustic accommodations with easy access to the beach. Essex River House Inn is a cozy bed and breakfast, located near Gloucester's downtown area.

How can I get around in Gloucester, MA?

You can get around Gloucester, MA in a few different ways:

  • By Car
  • By Public Transit
  • By Bicycle

The city offers two public bus routes, the Rockport and Gloucester Line, as well as bike paths and lanes throughout the area. You can also rent cars from several local rental services.

What are the must-visit tourist attractions in Gloucester, MA?

Gloucester, MA is a beautiful coastal town with a lot of interesting attractions for tourists to explore. Some of the must-visit tourist attractions in Gloucester, MA include:

  • Rockport Harbor
  • Cape Ann Museum
  • Gloucester Stage Company
  • Good Harbor Beach
From the historic Rockport Harbor to the Gloucester Stage Company, there is something for everyone to enjoy in Gloucester, MA. Whether you’re looking for a day at the beach or a cultural experience, Gloucester has it all.

About Gloucester

This waterfront city's history goes back to 1683 when it was first settled making it the oldest seaport in the U.S. The history provides lots of sightseeing opportunities for history buffs. The beaches allow beachcombers to enjoy the water.
  • Lighthouses: Gloucester has several lighthouses scattered in the area. Check out Eastern Point Lighthouse, Annisquam Harbor Light Station and Thatcher Island Twin Lights.
  • Beach Activities: There are several beaches for beach lovers to spend some time. Fish for cod, take a whale watching excursion, go snorkeling or paddle boarding.
  • Culture: Experience Gloucester's art culture at Rocky Neck, North America's oldest working art colony. The downtown features several outdoor historical statues that include Joan of Arc, a Fisherman's Memorial and a World War II statue.

What are the most popular vacation rental amenities in Gloucester?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Parking

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