Windham County Winter Rental
Cottage
10.0(46 Reviews)
3 Bedrooms
1 Bath
8 Guests
1200 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $326/Night
7 Nights - US $2,281
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1506.95 ft²
Spa
Skiing- Fireplace/Heating
View
US $257/Night
7 Nights - US $1,801
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
Kitchen
US $426/Night
7 Nights - US $2,981
Cottage
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
Parking
Air Conditioner
US $168/Night
7 Nights - US $1,179
Apartment
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
2098.96 ft²
- Fireplace/Heating
- View
- Parking
Internet
US $333/Night
7 Nights - US $2,329
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
825 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $347/Night
7 Nights - US $2,429
Hotel
7.6(36 Reviews)
4 Baths
387.5 ft²
Hot Tub- Fireplace/Heating
- Parking
- Air Conditioner
US $126/Night
7 Nights - US $880
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $264/Night
7 Nights - US $1,848
Hotel
6.1(131 Reviews)
1 Bath
355.21 ft²
- Hot Tub
- Fireplace/Heating
Pool- Balcony/Terrace
US $149/Night
7 Nights - US $1,043
House
9.8(9 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
Child Friendly
US $176/Night
7 Nights - US $1,235
House
10.0(23 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $743/Night
7 Nights - US $5,203
House
10.0(10 Reviews)
5 Bedrooms
3 Baths
10 Guests
3600 ft²
Private Pool- Fireplace/Heating
- Pool
- Ocean View
US $1,130/Night
7 Nights - US $7,909
Why Choose Rent By Owner for your Windham County Winter Rental?
What makes our Winter Rental 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.
Weekly Weather Forecast for Windham County
How to Book Your Windham County Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. 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 Winter Rental Amenities
What amenities can you expect?
Our Winter Rental 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
Other Places to Stay in Windham County, CT
Woodstock
Canterbury
Ashford
Plainfield
Chaplin Historic District
Hampton
Hampton Hill Historic District
Putnam
Thompson
Killingly
Pomfret
Danielson
Windham County Winter Rental Frequently Asked Questions
1. What are the top Winter 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 Winter Rentals in Windham County:
- La Quinta Inn & Suites by Wyndham Norwich-Plainfield-Casino
- Enjoy fishing and kayaking from waterfront cabin retreat in charming Woodstock
- Charming Lakefront Cottage
- Tranquil Waterfront Retreat with Private Dock and Stunning Views-Close to UCONN
- Spacious and new deluxe cabin in family campground in Northeastern CT
- Adorable a-frame cabin on the water
- Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
- Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!
- Famous Estate and Mansion with unmatched amenities for our prized guests!
- Private Villa Behind Famous Featherhill Mansion!
2. How many Winter Rentals are available in Windham County?
Currently, the total number of properties listed by RBO in 2026 is over 42 in the Windham County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Windham County.
More Rentals You May Like Near Windham County
House
10.0(10 Reviews)
3 Bedrooms
1 Bath
4 Guests
1410 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $489/Night
7 Nights - US $3,421
House
10.0(8 Reviews)
5 Bedrooms
2 Baths
10 Guests
2363 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $492/Night
7 Nights - US $3,443
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $857/Night
7 Nights - US $5,997
House
10.0(2 Reviews)
6 Bedrooms
6 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $480/Night
7 Nights - US $3,362
House
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
- Child Friendly
Security/Safety
US $920/Night
7 Nights - US $6,440
House
9.8(84 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $623/Night
7 Nights - US $4,360
Cottage
9.6(39 Reviews)
3 Bedrooms
1 Bath
8 Guests
1502 ft²
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $381/Night
7 Nights - US $2,667
House
9.6(39 Reviews)
3 Bedrooms
1 Bath
4 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
US $246/Night
7 Nights - US $1,722
House
9.6(21 Reviews)
3 Bedrooms
2 Baths
6 Guests
2150 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $248/Night
7 Nights - US $1,739
Cabin
9.4(34 Reviews)
3 Bedrooms
1 Bath
6 Guests
850 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $285/Night
7 Nights - US $1,994
House
7.4(3 Reviews)
1 Bedroom
2 Baths
10 Guests
2100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $459/Night
7 Nights - US $3,212
Other
10.0(18 Reviews)
4 Bedrooms
2 Baths
8 Guests
2800 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $466/Night
7 Nights - US $3,260
