Windsor County Accommodations
House
10.0(244 Reviews)
2 Bedrooms
1 Bath
4 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $186/Night
7 Nights - US $1,299
Apartment
10.0(9 Reviews)
1 Bedroom
1 Bath
4 Guests
150.69 ft²
Skiing- Fireplace/Heating
Pool
Air Conditioner
US $175/Night
7 Nights - US $1,225
Bed & Breakfast
10.0(51 Reviews)
1 Bedroom
1 Bath
Spa- Pool
- Balcony/Terrace
Breakfast
US $422/Night
7 Nights - US $2,956
Apartment
10.0(69 Reviews)
1 Bedroom
1 Bath
4 Guests
1700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $386/Night
7 Nights - US $2,700
House
10.0(3 Reviews)
3 Bedrooms
4 Baths
8 Guests
2497.23 ft²
Hot Tub- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,012/Night
7 Nights - US $7,086
Cabin
10.0(69 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $194/Night
7 Nights - US $1,358
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
21.53 ft²
- Skiing
- Fireplace/Heating
View
Parking
US $360/Night
7 Nights - US $2,519
House
10.0(62 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $430/Night
7 Nights - US $3,011
Apartment
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
1657.64 ft²
- Skiing
- Fireplace/Heating
- Breakfast
- Pet Friendly
US $535/Night
7 Nights - US $3,743
Cabin
10.0(57 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $326/Night
7 Nights - US $2,284
House
10.0(2 Reviews)
5 Bedrooms
2 Baths
12 Guests
2002.09 ft²
Private Pool- Skiing
- Fireplace/Heating
- Pool
US $500/Night
7 Nights - US $3,500
Apartment
10.0(55 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $121/Night
7 Nights - US $849
Why Choose Rent By Owner for your Windsor County Accommodations?
What makes our Accommodations 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 Windsor County
How to Book Your Windsor County Accommodations
What's our booking process?
Our platform allows you to browse a curated selection of accommodations. 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 Windsor County
Common Accommodations Amenities
What amenities can you expect?
Our Accommodations 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 Windsor County, VT
Ludlow
Bridgewater Corners
West Windsor
West Bridgewater
Woodstock
Quechee
Plymouth
Cavendish
Chester
Chester Depot
Proctorsville
Weston
Frequently Asked Questions about Windsor County Accommodations
1. What are the top Accommodations in Windsor County?
There are a lot of options in Windsor County. If you plan on staying in the Windsor County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Windsor County:
- Luxurious, Secluded, Ski Chalet, w/Country Decor & Hot Tub Near Okemo
- GORGEOUS LAKEFRONT - Autumn Splendor - Private Setting - 5 Mins to Okemo!
- Quiet Vermont Winter Getaway
- "The Crooked House" with A/C and sauna on private wooded lot near Killington
- 11 BR, 7 Bth, 1/2 mile to Okemo, Hot Tub, on Ski Shuttle, King Bed, Walk to Town
- Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
- Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village
- Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
- Scenic South Woodstock, Vermont home
- Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
2. How many Accommodations are available in Windsor County?
Currently, the total number of properties listed by RBO in 2026 is over 1504 in the Windsor County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Windsor County.
More Rentals You May Like Near Windsor County
Apartment
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
2131.25 ft²
- Skiing
- Fireplace/Heating
- Pool
- View
US $458/Night
7 Nights - US $3,204
Cabin
10.0(53 Reviews)
2 Bedrooms
2 Baths
8 Guests
1574 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $540/Night
7 Nights - US $3,780
House
10.0(51 Reviews)
2 Bedrooms
1 Bath
8 Guests
1200 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $459/Night
7 Nights - US $3,214
Apartment
10.0(40 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $256/Night
7 Nights - US $1,791
House
10.0(31 Reviews)
2 Bedrooms
1 Bath
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $319/Night
7 Nights - US $2,230
Apartment
10.0(27 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $253/Night
7 Nights - US $1,772
Cabin
10.0(25 Reviews)
2 Bedrooms
2 Baths
6 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $393/Night
7 Nights - US $2,753
House
10.0(24 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $318/Night
7 Nights - US $2,227
Cabin
10.0(19 Reviews)
1 Bedroom
1 Bath
4 Guests
540 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $284/Night
7 Nights - US $1,987
Cabin
10.0(15 Reviews)
1 Bedroom
1 Bath
4 Guests
540 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $294/Night
7 Nights - US $2,058
House
10.0(13 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $260/Night
7 Nights - US $1,819
Apartment
10.0(12 Reviews)
1 Bedroom
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $260/Night
7 Nights - US $1,819
