Best Vacation Homes in Windham County
1200 ft²
8 Guests
3 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $458/Night
For 7 Nights AU $3,204
1506.95 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Spa
- Skiing
- Fireplace/Heating
AU $361/Night
For 7 Nights AU $2,530
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Breakfast
- Kitchen
AU $295/Night
For 7 Nights AU $2,068
800 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $280/Night
For 7 Nights AU $1,959
301.39 ft²
13 Guests
6 Bedrooms
5 Bathrooms
Free Cancellation
Bed & Breakfast
- Balcony/Terrace
- View
- Breakfast
AU $445/Night
For 7 Nights AU $3,111
340 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $250/Night
For 7 Nights AU $1,753
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Cottage
- Fireplace/Heating
- Pet Friendly
- Parking
AU $313/Night
For 7 Nights AU $2,193
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
AU $228/Night
For 7 Nights AU $1,598
Windham County Luxury Rentals
3600 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
AU $1,426/Night
For 7 Nights AU $9,986
10 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
- Child Friendly
- Security/Safety
AU $1,292/Night
For 7 Nights AU $9,046
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $1,150/Night
For 7 Nights AU $8,051
1300 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $965/Night
For 7 Nights AU $6,756
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $871/Night
For 7 Nights AU $6,093
2100 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
AU $867/Night
For 7 Nights AU $6,072
16 Guests
8 Bedrooms
4 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
AU $838/Night
For 7 Nights AU $5,869
5500.36 ft²
14 Guests
7 Bedrooms
7 Bathrooms
House
- Parking
- Internet
- Child Friendly
AU $820/Night
For 7 Nights AU $5,742
Windham County Pet Friendly Vacation Rentals
7 Guests
2 Bedrooms
1 Bathroom
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
AU $367/Night
For 7 Nights AU $2,570
344.45 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
AU $128/Night
For 7 Nights AU $895
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
AU $128/Night
For 7 Nights AU $893
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $344/Night
For 7 Nights AU $2,409
22604.21 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- View
- Pet Friendly
- Parking
AU $458/Night
For 7 Nights AU $3,205
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $463/Night
For 7 Nights AU $3,241
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $560/Night
For 7 Nights AU $3,918
2363 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $583/Night
For 7 Nights AU $4,085
Windham County Large Vacation Homes
12 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
AU $675/Night
For 7 Nights AU $4,722
2368.06 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
AU $467/Night
For 7 Nights AU $3,271
5294 ft²
14 Guests
7 Bedrooms
7 Bathrooms
Family Friendly
House
- Hot Tub
- Skiing
- Fireplace/Heating
AU $936/Night
For 7 Nights AU $6,548
2098.96 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- View
- Parking
AU $467/Night
For 7 Nights AU $3,271
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Balcony/Terrace
- Internet
- Child Friendly
AU $2,423/Night
For 7 Nights AU $16,961
10 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $203/Night
For 7 Nights AU $1,419
5500 ft²
14 Guests
7 Bedrooms
7 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
AU $959/Night
For 7 Nights AU $6,716
14 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- Kitchen
AU $701/Night
For 7 Nights AU $4,906
Why Choose Rent By Owner for your Windham County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windham County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience and help you make the most of your stay in this beautiful region by aligning your plans with the local seasons and climate.
Peak Season Highlights
Summer (June to August)
During the summer months, this area experiences warm weather, making it ideal for outdoor activities and exploring the natural beauty of the region. Expect lively local events and a vibrant atmosphere in your vacation rentals.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn is a peak season here, with stunning foliage attracting visitors seeking scenic views and outdoor excursions. Vacation rentals are perfect during this time to enjoy the colorful landscape and crisp air.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
This quieter period offers a peaceful ambiance, ideal if you prefer a more relaxed experience away from the crowds. Cozy up in your vacation rental as you enjoy the serene winter scenery.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Spring (March to May)
Early spring sees fewer visitors, providing a tranquil environment for exploring and relaxing. Enjoy the budding nature and mild temperatures while staying at your preferred vacation rental.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Windham County
How to Book Your Windham County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windham County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining on a spacious patio or deck with scenic views of the surrounding landscape.
- Take advantage of private gardens or lush lawns perfect for relaxing or outdoor activities.
- Make use of outdoor fire pits or fireplaces ideal for evening gatherings in the fresh air.
- Access private pools or hot tubs that provide a luxurious way to unwind after exploring the area.
- Explore nearby hiking or walking trails directly from your rental, embracing the natural beauty here.
- Use outdoor grills or barbecues for preparing delicious meals amid the tranquil setting.
- Benefit from ample parking space, making it convenient to explore the region's outdoor attractions.
Top Attractions Around Windham County
What attractions are nearby?
In this scenic region, you can explore outdoor activities such as hiking, fishing, and wildlife viewing, all just moments from your chosen vacation rentals in Windham County, Connecticut.
Family Activities
- Windham County Quest: Embark on a family-friendly outdoor adventure exploring scenic trails and nature preserves that highlight the area's natural beauty.
- Local History Museum Tour: Discover the region’s rich history through engaging exhibits and interactive displays perfect for curious young minds.
- Community Festivals and Events: Participate in seasonal festivals that offer entertainment, crafts, and local cuisine, creating lasting family memories.
- Recreational Parks and Playgrounds: Spend quality time at well-maintained parks with playgrounds, lakes for fishing, and picnic areas within the region for a relaxing family day out.
Adult Activities
- Hiking and Nature Walks: Explore scenic trails within the region that offer a peaceful escape into lush landscapes, perfect for outdoor enthusiasts staying in nearby vacation rentals.
- Visit Local Farms and Farmers' Markets: Discover fresh produce and artisan goods by visiting charming farms and markets that showcase the area's agricultural heritage.
- Historic Landmarks and Museums: Engage with the region’s rich history by touring historic sites and museums that provide insight into its cultural past.
- Wine Tasting Tours: Enjoy sampling local wines at nearby vineyards, making for a relaxing and flavorful experience during your stay here.
Other Places to Stay in Windham County, CT
Woodstock
Canterbury
Ashford
Plainfield
Hampton
Hampton Hill Historic District
Putnam
Dayville
Thompson
Killingly
Pomfret
Danielson
Windham County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar to align your stay with festivals or activities that showcase Windham County’s unique charm.
- Explore Outdoor Attractions: Take advantage of the region's scenic parks and hiking trails, making outdoor adventures a central part of your visit.
- Choose Your Location Wisely: Select a vacation rental in a convenient area to easily access local shops, dining, and natural landmarks here.
- Discover the Authentic Flavor: Sample local cuisine and visit nearby markets to immerse yourself in the regional culture during your stay.
Transportation Options
- Western Connecticut Airport: This regional airport offers convenient flights for travelers visiting the area and nearby destinations.
- Amtrak Service: The train station provides reliable rail connections, making it easy to explore Connecticut and beyond from here.
- Local Bus Services: Public transportation options are available within the region, offering an affordable way to navigate locally.
- Car Rentals: Numerous rental agencies are accessible in the area, giving you the flexibility to explore Windham County at your own pace.
Local Customs Options
- Local Craftsmanship: You will notice a rich tradition of handcrafted goods, reflecting the area's appreciation for artisanal skills and local materials.
- Community Festivals: Participate in seasonal festivals that celebrate regional history and foster a sense of togetherness among residents and visitors alike.
- Farm-to-Table Cuisine: Savor the region’s culinary offerings rooted in farm-fresh ingredients and traditional cooking methods unique to here.
- Historic Preservation: Respect for historic architecture and landmarks is evident, highlighting the community’s dedication to maintaining its heritage.
Frequently Asked Questions About Windham County?
1. What are the top vacation rentals in Windham County?
There are a lot of options in Windham County. If you plan on staying in the Windham County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windham County:
- Magical Waterfront Cottage! Pet friendly!
- The Watson Boutique Bed & Breakfast
- The Carriage House at Chaprae Hall
- Stunning Lakefront Escape! Book Your Dream Getaway!
- Beautiful lake front home. Amazing view!
- A fun filled,family friendly, farmhouse home, rural,but close to all amenities
- Killingly Barnyard Studio in Wine Country!
- Cozy 1-bedroom cottage with WiFi, AC in charming Windham
- Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
- Luxurious 5-BR home in peaceful 3+-acre setting with heated, salt-water pool!
2. How many vacation rentals have private pools in Windham County?
There are 1 vacation rentals with private pools near Windham County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windham County are best for families?
If you are looking for a family-friendly vacation home in Windham County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windham County:
4. How many Rentbyowner vacation rentals are available in Windham County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 94 in the Windham County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windham County.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it's important to review the specific listing details or contact the property owner directly to understand their terms and any applicable fees.
6. Are pets allowed in the vacation rentals I want to book?
Pet policies are set by individual hosts; please check the listing details or reach out to the owner to confirm if pets are permitted during your stay in the region.
7. How do I find the most suitable rental for my needs in this destination?
You can filter search results based on amenities, location, and price range to find a property that best fits your preferences, or contact the host for additional information.
8. What are the check-in and check-out procedures for vacation homes here?
Check-in and check-out times are specified in each listing; it’s advisable to communicate with the property owner for detailed instructions or any special requirements.
9. Is there a minimum stay requirement for booking a vacation rental in this area?
Many properties have minimum stay requirements that vary seasonally or by listing; please review each property's terms or contact the owner for clarification.
Windham County Top Rated Vacation Rentals
2800 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Other
- Fireplace/Heating
- Pool
- Ocean View
AU $646/Night
For 7 Nights AU $4,523
1000 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $246/Night
For 7 Nights AU $1,723
290.63 ft²
8 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Fireplace/Heating
- Pool
AU $163/Night
For 7 Nights AU $1,141
AU $129/Night
For 7 Nights AU $906
AU $209/Night
For 7 Nights AU $1,465
828.82 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pool
- Parking
AU $701/Night
For 7 Nights AU $4,906
AU $598/Night
For 7 Nights AU $4,183
8 Guests
3 Bedrooms
1 Bathroom
Ocean View
Cabin
- Oceanfront
- Fireplace/Heating
- Pool
AU $494/Night
For 7 Nights AU $3,457
