Windham County vacation rentals

We found 205 vacation rentals — enter your dates for availability

Discover a selection of 29 homes, 13 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.

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Find out more about Windham County

Why visit Windham County

  • Outdoor Adventures: Enjoy hiking, paddling, and exploring nature reserves that showcase Windham County's scenic beauty.
  • Charming Towns: Discover picturesque towns filled with friendly locals and rich history, perfect for leisurely strolls.
  • Diverse Accommodations: Choose from cozy cottages to modern apartments, catering to all vacation styles and budgets.
  • Eco-Friendly Activities: Engage in sustainable tourism with various outdoor experiences that promote environmental awareness.
  • Nearby Attractions: Venture to nearby Washington County for additional exciting experiences and attractions.

Popular types of accommodation in Windham County

Discover the charm of Windham County with a variety of vacation rentals tailored to your needs. From cozy cottages to spacious houses and modern apartments, you’ll find the perfect fit for your getaway. Explore our selection of new construction homes and custom options to enjoy the latest in comfort and style. Whether you're looking for a relaxing retreat or an adventure-filled escape, our transparent listings ensure you're well-informed every step of the way.

  • Cottages: The top choice for vacation rentals in Windham County, offering charming and cozy accommodations perfect for a relaxing getaway.
  • Houses: A popular option for larger groups or families, providing spacious and comfortable home-like settings.
  • Apartments: Ideal for solo travelers or couples, these rentals offer convenience and a taste of local life.
  • Cabins: Rustic retreats nestled in nature, perfect for those looking to escape and enjoy the outdoors.**

Top attractions in Windham County

Windham County, Connecticut, is perfect for outdoor enthusiasts and couples seeking a scenic getaway. With a variety of attractions, including nature reserves, lakes, and urban parks, visitors can immerse themselves in eco-friendly adventures. Whether you're looking to hike, paddle, or simply enjoy the natural beauty, Windham County offers a unique blend of outdoor experiences that cater to all types of travelers.

  • Eastern Connecticut State University: A vibrant campus that blends modern architecture with a lively atmosphere, Eastern Connecticut State University is perfect for those who appreciate educational environments and city vibes.
  • Brooklyn Recreation Park: This family-friendly park offers a range of outdoor activities amidst beautiful greenery, making it an ideal spot for eco-conscious visitors seeking relaxation and fun.
  • Moosup Pond Beach: A picturesque lake setting perfect for romantic getaways, Moosup Pond Beach provides stunning scenery and ample opportunities for outdoor recreation.

Things to do recommended for couples

For a memorable couple's getaway in Windham County, embark on an exhilarating skydive at Skydive Danielson, savor exquisite wines at Taylor Brooke Winery, and enjoy a romantic afternoon outdoors at Sharpe Hill Vineyard. Each experience offers a unique blend of adventure and romance, perfect for couples.

Things to do recommended for families

Families visiting Windham County can explore the beautiful trails at the Natchaug State Forest, enjoy a fun-filled day at the Willimantic Food Co-op, and discover hands-on exhibits at the Connecticut Science Center, making for an exciting and educational experience for all ages.

Things to do recommended for groups

Experience thrilling motor racing at Thompson International Speedway, enjoy shopping and entertainment at Killingly Shopping Center, and unwind with a round of golf at Roseland Park Golf Course. Windham County offers a perfect blend of adventure, leisure, and fun for your group getaway.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windham County

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences in your search. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Windham County with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group activities. The good news is that you can easily apply filters for all of these options and more on Vrbo.
  • Traveling to Windham County with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you might want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windham County: For many families, no trip feels whole without their furry companion by their side. If that resonates with you, take a look at Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with food bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windham County: If you're in search of vacation rentals offering discounts for stays of a month or longer, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking spot, a well-equipped kitchen, or a private pool in your search for the best fit.

Where to stay in Windham County

Windham County, Connecticut, offers a delightful blend of outdoor adventures and charming neighborhoods perfect for your vacation. Explore picturesque towns with friendly locals, enjoy scenic landscapes, and dive into the area’s rich history. Whether you're seeking budget-friendly options or romantic getaways, Windham County has something for everyone. Don’t forget to check out nearby Washington County for additional attractions and experiences that will make your trip unforgettable.

  • Plainfield: Nestled in the scenic landscape of Windham County, Plainfield is a charming city that offers a blend of urban excitement and outdoor adventure. Ideal for couples and nature enthusiasts, visitors can enjoy music concerts and unwind at local resorts or golf courses. The area is home to noteworthy attractions, including a historic college university and serene beaches, perfect for a romantic getaway or family outings. The city's event conference venue also hosts various gatherings, making it a vibrant hub for entertainment and leisure.
  • Willimantic: Known as the Thread City for its rich textile history, Willimantic is a cultural gem in Windham County. This city attracts travelers looking for a mix of cultural and romantic experiences. Educational institutions and modern colleges add to the vibrant atmosphere, where visitors can enjoy live music concerts and play a round of golf. Key landmarks include historic college universities and an event conference venue, offering insights into the area's educational heritage while providing ample opportunities for exploration and enjoyment.
  • Putnam: Putnam is a delightful city that invites visitors to experience its charming outdoor environment and lively urban scene. Known for its romantic ambiance, Putnam offers a variety of activities, from music concerts to thrilling motor racing events. The city is home to a stunning lake, a vibrant stadium, and an event conference venue, which provide both relaxation and entertainment options. Whether you're looking to enjoy the outdoors or explore local attractions, Putnam is a perfect stop on your Windham County adventure.

Booking with Vrbo is simple

Are you hoping to save some money on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your journey.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a convenient way to plan your journeys, pick up right where you left off, and manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • Taylor Brooke Winery (8.3 mi / 13.3 km)
  • Roseland Park Golf Course (9.6 mi / 15.4 km)
  • Mohegan Sun Golf Club (14.7 mi / 23.6 km)
  • Dudley Hill Golf Club at Nichols College (15.5 mi / 24.9 km)
  • Brown and Hopkins Country Store (17.3 mi / 27.9 km)
  • Stafford Motor Speedway (19.1 mi / 30.7 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:

  • Brooklyn Recreation Park (3.8 mi / 6.2 km)
  • Moosup Pond Beach (9.2 mi / 14.8 km)
  • Quaddick Reservoir (12.1 mi / 19.5 km)
  • Buck Hill Management Area (14.6 mi / 23.5 km)
  • Hopeville Pond State Park (15.8 mi / 25.5 km)
  • Lake Chaubunagungamaug (16.4 mi / 26.4 km)

Frequently asked questions

What is the best area to stay in Windham County when booking a vacation rental?
Ashford is one of the most popular neighborhoods for a Vrbo vacation home in Windham County. Take a look at our collection of relaxing properties and then go out and experience this destination like a local.
What is the most popular type of vacation rental accommodation in Windham County?
The most sought-after types of vacation rentals in Windham County are cottages. Prefer something different? Vrbo offers a variety of options to match the unique needs of our guests, so you'll see vacation homes in all sizes, and for all budgets. The ideal fit is waiting for you — lock in yours today.
How much does it cost to rent a vacation rental in Windham County?
Several factors can affect how much you pay for a vacation rental in Windham County, like the length of stay, type of property and season. Still, all of our vacation homes have something in common — unbeatable value. Simply add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Windham County?
The average price for a vacation home close to the beach in Windham County depends on when you're visiting the area and the type and size of property you're searching for. You can easily find prices on Vrbo by entering your travel dates and destination. Then use the filter tool to choose the number of bedrooms and amenities that you need, like air conditioning, WiFi and a pool.
Are there pet-friendly vacation rentals in Windham County?
With three vacation rentals that host pets, your furry little friend can join you on your Windham County break. Use our filter tool to browse our pet-friendly vacation rentals and find your pawfect vacation home on Vrbo.
Are there large group vacation rentals in Windham County?
You'll find four properties in Windham County that can sleep 10 or more people. Whether you're planning a family vacation or some kind of special event, there's plenty of room to get your group together under the same roof.
Are there one-bedroom vacation rentals in Windham County?
Yes, there are 9 one-bedroom properties in Windham County to select from. A one-bedroom vacation rental is a superb choice if it's only the two of you or if you're vacationing alone. Add in more convenience, privacy and space than a regular hotel, and you've got yourself a break to remember.
Can I find two-bedroom vacation rentals in Windham County?
Windham County has six two-bedroom vacation properties to choose from. Go for a vacation home with all the comfort and space you need at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Windham County?
You'll have a choice of 20 vacation rentals with WiFi in Windham County. If you'd like to disconnect from daily life during your break, but still want to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Windham County?
Decide on your travel dates and then use the filter tool to find vacation rentals with air conditioning in Windham County on Vrbo. With 26 air-conditioned properties to choose from here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a vacation rental in Windham County?
The minimum required age is usually 16, 18 or 21. It can vary across properties on Vrbo, so check the rules of your chosen Windham County stay before booking your trip.
How long can I rent a vacation rental in Windham County for?
The amount of time you can book a Windham County vacation rental for differs depending on the property. Just enter your travel dates to browse available options offering longer term stays. They include all you need to make your extended break more enjoyable and comfortable, like air conditioning and laundries. Some properties may also offer discounted weekly or monthly prices, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Windham County?
Whether you're interested in one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to score some fabulous bargains and discounts on Vrbo. From weekend trips to extended vacations, we've got you covered for your next Windham County escape.

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