348+ Private Villas and Holiday Rentals in Gloucester |
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Gloucester Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Gloucester

Discover more than 348 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 984.49 ft², with nightly prices averaging US $533.

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.

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Top Accommodation Types in Gloucester

Type Count
Vacation Homes 230
Holiday Apartments 67
Cottages 22
Villas 3

Use these Quick Filters to Find a Holiday Rental in Gloucester

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Gloucester.

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

Top Attractions Around Gloucester, MA

Casai offers a large selection of top attractions around Gloucester . Research things to do on your vacation before you visit Gloucester.


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

Other Places to Stay in Gloucester, MA


Dogtown 473 Properties
Good Harbor Beach 406 Properties
Plum Cove Beach 294 Properties
Annisquam 270 Properties
Northeast Hospital Corporation - Addison Gilbert Campus 262 Properties
Sargent House Museum 244 Properties
Cape Ann Historical Museum 244 Properties
Cape Ann Museum 244 Properties
Gloucester Unitarian Universalist Church 243 Properties
Lucky 7 Arcade 239 Properties
Schooner Adventure 237 Properties
Magnolia 74 Properties

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 holiday rentals have private pools in Gloucester?

Discover a selection of holiday rentals with private pools near Gloucester with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Gloucester are best for families?

If you're searching for a family-friendly holiday home in Gloucester, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Gloucester:

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

As of 2025, Casai boasts over 348 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) 
Neighborhood Property Count
Annisquam Vacation Rentals in Gloucester, Massachusetts 270

People Also Ask

There are 348 Gloucester, MA Holiday Rentals

Recently Booked Holiday Rentals in Gloucester