Gloucester Holiday Rentals

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Compare Holiday Rentals, Villas & Resorts in Gloucester

409 villas and rentals
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About Casai's Private Villas and Holiday Rentals in Gloucester

Discover more than 409 vacation rentals available in Gloucester. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Gloucester.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Gloucester, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Gloucester. On average, places to stay near Gloucester offer 1058.39 ft², with nightly prices averaging US $608.

With Casai, finding and comparing holiday rentals in Gloucester is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Other Places to Stay in Gloucester, MA


Dogtown 543 Properties
Good Harbor Beach 458 Properties
Annisquam 346 Properties
Plum Cove Beach 323 Properties
Northeast Hospital Corporation - Addison Gilbert Campus 316 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 92 Properties

There are 409 Gloucester, MA Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Gloucester

Frequently Asked Questions About Gloucester?

What are the top holiday rentals in Gloucester?

With numerous options available in Gloucester, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Gloucester:

How many Casai.nz holiday rentals are available in Gloucester?

As of 2026, Casai boasts over 409 properties listed in the Gloucester area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Gloucester.

Nearby Neighborhood (1)

NeighborhoodProperty Count
Annisquam Vacation Rentals in Gloucester, Massachusetts 346