Gloucester, MA, USA

Gloucester, MA, USA

We found 394 vacation rentals — enter your dates for availability


Find the best place to stay — Gloucester

Where to stay near Gloucester, MA?

Our 2018 property listings offer a large selection of 394 vacation rentals near Gloucester. From 221 houses to 60 apartments, 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.

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.

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.

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.

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!

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.