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

See a medieval castle in Gloucester

As the oldest seaport in the U.S.A and a town with a rich maritime history, you should make time to visit Fishermen’s Memorial Monument. The monument—dedicated to the memory of fishermen lost at sea—is impressive in itself, but the beautiful surrounding gardens and panoramas across the ocean make it a must-see attraction. History buffs will love taking a tour of Hammond Castle, a beautiful home built in the 1920s in the style of a medieval castle. Cape Anne Museum provides a fascinating insight into the art and culture of the local area.

Activities

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.

Weather

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

Explore the beautiful Cape Anne with a trip to Gloucester

Gloucester is positioned on the coast of Cape Anne in Massachusetts. The Atlantic Ocean provides the opportunity to try many fantastic activities, from fishing to whale watching. Those looking to top up their tan will be pleased to learn there’s a choice of beaches that are never far from Gloucester vacation rentals—from the popular Good Harbor Beach to the smaller, more secluded Half Moon Beach. If you’re planning to hire a boat, be sure to visit nearby Ten Pound Island, where you can enjoy the most beautiful sunset.

How to get there

How to get 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're unable to find a flight that fits your schedule, you can also fly into Lawrence, MA (LWM-Lawrence Municipal), which is 24.3 mi (39.1 km) away.

If you'd rather travel by train, make your way to Gloucester Station or West Gloucester Station to see more of the city.

Where to stay around Gloucester?

Our 2019 property listings offer a large selection of 413 vacation rentals near Gloucester. From 225 Houses to 56 Cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Gloucester for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Gloucester?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Gloucester:

  • Annisquam: 25 vacation rentals
  • Hampton Beach: 201 vacation rentals
  • Seabrook Beach: 87 vacation rentals
  • South Boston: 785 vacation rentals
  • Essex: 520 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Gloucester?

HomeAway offers a large selection of vacation rentals near lovely places in Gloucester. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Wingaersheek Beach: 279 vacation rentals
  • Good Harbor Beach: 605 vacation rentals
  • Maritime Gloucester: 616 vacation rentals
  • Rocky Neck Art Colony: 610 vacation rentals
  • Plum Cove Beach: 841 vacation rentals

But there are many other points of interest around Gloucester listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Gloucester?

Yes, of course. HomeAway has 225 Houses in Gloucester. Our other popular types of vacation rentals in Gloucester include:

  • Cottages: 56 rentals available
  • Condos/Apartments: 95 rentals available
  • Bungalows: 56 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cabins and more.

Can I find a vacation rental with pool in Gloucester?

Yes, you can select your preferred vacation rental with pool among our 11 vacation rentals with pool available in Gloucester. Please use our search bar to access the selection of vacation rentals available.