Discover a selection of 305 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 air conditioning and kitchens. Prices start at $97 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.
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.


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

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.

How many vacation rentals are available around Gloucester, MA?

Our 2020 property listings offer a large selection of 305 vacation rentals around Gloucester. From 172 house rentals to 48 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a seaside property in Gloucester?

Perhaps it's the magnificent sea views, or maybe it's the chance to chill out from sunrise to sunset. There's just something about a beach getaway that appeals to all of us. Vrbo has 133 beachside vacation homes to pick from. Want to try a different setting? See if any of our other properties float your boat. Our selection here includes:

  • 103 ocean-view vacation rentals.
  • 77 water-view vacation rentals.
  • 59 beach vacation rentals.

Can I rent a house in Gloucester?

Wave goodbye to standardized, cookie cutter chain-hotel rooms. Our house vacation rentals each have their own unique personalities — as well as all the space you could need! There are 150 houses currently available on Vrbo. Prices begin at $50 per night. If that doesn't agree with your crew's style, we've got a range of different rental options to select from, such as:

  • Apartment: 46 vacation homes. Prices start from $115 per night.
  • Cottage: 33 vacation homes. Prices start from $100 per night.
  • Condo: 16 vacation homes. Prices start from $110 per night.

Can I stay in Gloucester in a large group?

It can be tough finding time to meet up with friends and family members. A group vacation is a perfect opportunity to be reunited. If you were planning to kick back under the same roof, Vrbo has options to suit. House vacation homes are the favorite option for large groups of visitors, with 31 available here. If you're planning on traveling in a larger group, the vacation rental options that can cater to you include:

  • If yours is a squad of 6, we have 47 vacation homes just right for that size. Stay a night from just $164.
  • If you've got 8 in your squad, you'll be thrilled to hear that there are 38 vacation homes perfect. You can book one for as little as $180 per night.
  • Traveling with 7 guests? We have 26 vacation homes that will be ideal. Prices begin at just $160 per night.

You and all your besties will be well looked after when you book your Gloucester adventure through us!

Where are the cheapest rentals in Gloucester?

Teeny tiny hotel rooms are no place to spend those precious vacation moments! Uncover our value-packed rentals today and ensure everyone has enough room to spread out. When it comes to finding a great deal, the first place you look ought to be Ipswich. Here, Vrbo has 6 rentals at an average price of $124 per night. Prides Crossing is another place worth considering. We have 5 rentals here, and the average price is around $284 per night.