93+ Private Villas and Holiday Rentals in Windham County |
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Windham County Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Windham County

Discover more than 93 vacation rentals available in Windham County. 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 Windham County.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windham County, 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 Windham County. On average, places to stay near Windham County offer 970.56 ft², with nightly prices averaging US $311.

With Casai, finding and comparing holiday rentals in Windham County 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 Windham County

Type Count
Vacation Homes 44
Holiday Apartments 10
Cottages 10
Villas 1

Use these Quick Filters to Find a Holiday Rental in Windham County

★ 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 Windham County.

Weather in Windham County, CT

View the weather forecast for Windham County before booking your Windham County 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 Windham County, CT

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


Brooklyn Golf Course
Bradley Playhouse
Eastern Connecticut State University
Canterbury Green
Chaplin Museum
Woodstock Golf Course
Killingly Shopping Center
Skydive Danielson
Thompson International Speedway
Brooklyn Country Club
Taylor Brooke Winery
Little River Plaza Shopping Center
Old Furnace State Park
New England Center for Contemporary Art at Brooklyn
Sharpe Hill Vineyard
Brooklyn Recreation Park
Martha's Herbary
Davis Park
Squaw Rock State Park
Rotary Park
Roseland Cottage
Brooklyn Common Shopping Center
Tinkerville Brook Reserve
Harrisville Golf Course
Nathaniel Lyon Memorial Park
Nickerson Park
Moosup Pond Beach
Roseland Park Golf Course
Killingly Pond State Park
Quaddick Reservoir

Other Places to Stay in Windham County, CT


Woodstock 155 Properties
Canterbury 138 Properties
Ashford 131 Properties
Plainfield 103 Properties
Hampton 96 Properties
Hampton Hill Historic District 95 Properties
Putnam 44 Properties
South Woodstock 42 Properties
Thompson 33 Properties
Pomfret 29 Properties
Killingly 28 Properties
Danielson 24 Properties

Frequently Asked Questions About Windham County?

What are the top holiday rentals in Windham County?

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

How many holiday rentals have private pools in Windham County?

Discover a selection of holiday rentals with private pools near Windham County 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 Windham County are best for families?

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

How many Casai.com holiday rentals are available in Windham County?

As of 2026, Casai boasts over 93 properties listed in the Windham County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windham County.


People Also Ask

There are 93 Windham County, CT Holiday Rentals

Recently Booked Holiday Rentals in Windham County