359+ Rental Villas and Private Getaways in Gloucester |
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Gloucester Villa Rentals

About Gloucester Vacation Rentals

Most visitors think of Boston when they plan a vacation in Massachusetts, but the seaside town of Gloucester is worth a visit too. This charming coastal community is home to some wonderful private villas and cottages, perfect for a relaxing getaway. If you're looking for some peace and quiet away from the hustle and bustle of city life, check out these idyllic Gloucester accommodations. With a variety of options to choose from, you're sure to find the perfect place to stay during your visit to this charming coastal town. From elegant estates with stunning ocean views to cozy cottages tucked away in the forest, there's something for everyone when it comes to private villas and cottages in Gloucester. So why not ditch the traditional hotel this time around and explore all that Gloucester has to offer?

There are more than 359 incredible getaway rentals that are available in Gloucester. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Gloucester.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Gloucester, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Gloucester. Places to stay near Gloucester are 973.67 ft² on average, with prices averaging CA $711 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Gloucester. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Gloucester

Type Count
Vacation Homes 240
Holiday Apartments 69
Cottages 23
Villas 3
B&B 1

Use these Quick Filters to Find a Vacation Rental in Gloucester

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Gloucester with BedroomVillas.

Weather in Gloucester, MA

View the weather forecast for Gloucester before booking your Gloucester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Gloucester's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Gloucester's Research Top Attractions For Your Vacation


Good Harbor Beach
Wingaersheek Beach
Hammond Castle
Maritime Gloucester
Stage Fort Park
Lucky 7 Arcade
Eastern Point Lighthouse
Niles Beach
The Gorton Theatre
Half Moon Beach
Mount Ann Park
Dogtown
Cape Ann Museum
Plum Cove Beach
Ravenswood Park
Sargent House Museum
Capt Bill & Sons Whale Watch
Fishermen's Memorial Monument
Cape Ann Historical Museum
Gloucester Unitarian Universalist Church

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Dogtown 543 Properties
Good Harbor Beach 458 Properties
Plum Cove Beach 323 Properties
Northeast Hospital Corporation - Addison Gilbert Campus 316 Properties
Annisquam 310 Properties
Cape Ann Museum 286 Properties
Cape Ann Historical Museum 284 Properties
Sargent House Museum 283 Properties
Schooner Adventure 282 Properties
Gloucester Unitarian Universalist Church 280 Properties
Lucky 7 Arcade 279 Properties
Magnolia 85 Properties

Frequently Asked Questions About Gloucester?

What are the top hotels or resorts in Gloucester?

We provide an array of great vacation destinations in Gloucester. If you are looking to stay in or around the Gloucester area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Gloucester:

How many vacation rentals have private pools in Gloucester?

We have 2 luxury villas and vacation rentals featuriung a private pool in and near Gloucester. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Gloucester is best for families?

Searching for a family-friendly getaway in Gloucester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Gloucester?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 359 in the Gloucester area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Gloucester. 

Nearby Neighborhood (1) 
Neighborhood Property Count
Annisquam Rental Villas and Private Getaways in Gloucester, Massachusetts 310

People Also Ask

There are 15 hotels in Gloucester and 312 rentals

Recently Booked Hotels, Resorts, or Rentals in Gloucester