Windham County Vacation Rentals, Connecticut: house rentals & more

Discover a selection of 26 homes, 14 apartments, and other vacation rentals in Windham County that are perfect for your trip. Vacation homes provide the best amenities for your family, friends, or furry companion, like air conditioning and cable TV. At the end of the day, you'll find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Popular cities in Windham County

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Find the best place to stay - Windham County

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Sleeps 8 · 4 bedrooms · 2 bathrooms

Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Top rated rentals - Windham County

Great Place

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value

Choose a vacation rental for your Windham County getaway

Learn about the unique charm of Windham County with a stay in a private vacation home. There's no shortage of things to see and do in the area.Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Windham County

Do you want to find attractions to visit while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Windham County has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

Brooklyn Country Club (5.2 mi / 8.3 km)
Taylor Brooke Winery (8.3 mi / 13.3 km)
Mohegan Sun Golf Club (14.7 mi / 23.6 km)
Stafford Motor Speedway (19.1 mi / 30.7 km)
Leyden Farm Vineyards & Winery (19.3 mi / 31.1 km)
Buttonwood Farm & Ice Cream (19.8 mi / 31.8 km)

Exploring the natural landscape of Windham County

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Windham County is a great spot to appreciate mother nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

Nickerson Park (6.1 mi / 9.9 km)
Moosup Pond Beach (9.2 mi / 14.8 km)
Roger Lake (9.9 mi / 15.9 km)
Quaddick Reservoir (12.1 mi / 19.5 km)
Tinkerville Brook Reserve (13.1 mi / 21.1 km)
Buck Hill Management Area (14.6 mi / 23.5 km)

Frequently asked questions

What is the best area to stay in Windham County when booking a vacation rental?

One of the most in-demand neighborhoods for a Windham County vacation home is Ashford. When you book your vacation rental with Vrbo, you will have the whole place to yourself. So you won’t have to share it with anybody apart from your group.

What is the most popular type of vacation rental accommodation in Windham County?

Based on our data, houses are the most desirable type of vacation property in Windham County. But having said that, everyone’s idea of an epic trip can differ. Vrbo has vacation rentals of all sizes, shapes and budgets, and we’ll help you discover your perfect match.

How much does it cost to rent a vacation rental in Windham County?

Property type, season and length of stay are among the factors that can determine the price of a vacation home. Simply click on your dates of travel to find your ideal escape. From comfy cabins to sprawling villas, all Vrbo vacation rentals provide unbeatable value.

How much does it cost to rent a beach house in Windham County?

Prices for beach houses in Windham County can differ depending on the size and style of the property and when you plan to travel. Simply enter your travel dates into Vrbo and how many guests to view your vacation rental options and prices. From there you can use the filters to narrow your search by ratings, amenities, nearby activities and more.

What are popular rental amenities in Windham County?

Some of the most popular rental amenities people are searching for in Windham County are a barbecue grill, a fridge and a microwave oven. Whether you’re going on vacation with family, friends or even pets, Vrbo vacation properties feature the best amenities for fun and relaxation with the people that matter most.

Are there large group vacation rentals in Windham County?

You’ll find nine vacation homes in Windham County that can host a group of five or more guests. From family getaways to events like a friend’s birthday, these stays have enough room to kick back with your favorite people.

What are the top attractions for families in Windham County?

There are tons of awesome things to see and do with the family in Windham County, including:

Thompson International Speedway
Killingly Shopping Center
Moosup Pond Beach

Can I find two-bedroom vacation rentals in Windham County?

Windham County has five two-bedroom vacation rentals to select from. Go for a vacation home with all the comfort and privacy you’re looking for at a price that’s hard to resist on Vrbo.

Are there vacation rentals with WiFi in Windham County?

Windham County has 16 vacation rentals with WiFi, so you’ll be able to stay connected during your vacation. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with the family to checking emails, these Vrbo homes make it easy to get online.

How old do you have to be to rent a vacation rental in Windham County?

The minimum required age is typically 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your preferred Windham County vacation home before making a booking.

How long can I rent a vacation rental in Windham County for?

How long you can rent a vacation rental in Windham County varies according to the property. Just enter your selected travel dates to view a list of options offering extended stays. With tons of features such as full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to find somewhere perfect to call your home away from home in Windham County.