Gloucester Holiday Rentals

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Compare Villas, Resorts, & Rentals in Gloucester

412 villas and rentals
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Luxury Holiday Rentals in Gloucester

Over 403+ Luxury Holiday Rentals in or Near Gloucester
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Top-Rated Holiday Rentals with a Pool in Gloucester

Over 17+ The Best Private Villas and Holiday Rentals in Gloucester with a Pool
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Pet-Friendly Holiday Rentals in Gloucester

Over 102+ Pet-Friendly Holiday Rentals in or Near Gloucester
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Large Holiday Rentals and Private Villas in Gloucester

Over 74+ Large Holiday Rentals and Private Villas in or Near Gloucester
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Wheelchair Accessible Holiday Homes in Gloucester

Over 10+ Wheelchair Accessible Holiday Homes in or Near Gloucester
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Gloucester Private Villas and Holiday Homes Under $200

Over 23+ Gloucester Private Villas and Holiday Homes Under $200
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Instantly Bookable Holiday Homes in Gloucester

Over 190+ Instantly Bookable Holiday Homes in or Near Gloucester
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Book a Last Minute Place to Stay in Gloucester

About Casai's Private Villas and Holiday Rentals in Gloucester

Discover more than 412 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 1055.46 ft², with nightly prices averaging US $612.

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 near the Gloucester, MA


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Schooner Adventure 282 Properties
Gloucester Unitarian Universalist Church 280 Properties
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Magnolia 92 Properties

There are 412 Gloucester, MA Holiday Rentals

Recently Booked Holiday 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.com holiday rentals are available in Gloucester?

As of 2026, Casai boasts over 412 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