Windsor County Accommodations
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $139/Night
For 7 Nights US $972
2497.23 ft²
8 Guests
3 Bedrooms
4 Bathrooms
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,015/Night
For 7 Nights US $7,105
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $295/Night
For 7 Nights US $2,067
900 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $189/Night
For 7 Nights US $1,321
1657.64 ft²
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
Apartment
- Skiing
- Fireplace/Heating
- Pet Friendly
US $535/Night
For 7 Nights US $3,743
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $229/Night
For 7 Nights US $1,605
2002.09 ft²
12 Guests
5 Bedrooms
2 Bathrooms
House
- Private Pool
- Skiing
- Fireplace/Heating
US $500/Night
For 7 Nights US $3,500
1700 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $291/Night
For 7 Nights US $2,037
2131.25 ft²
6 Guests
1 Bedroom
3 Bathrooms
Family Friendly
Apartment
- Skiing
- Fireplace/Heating
- Pool
US $450/Night
For 7 Nights US $3,150
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $185/Night
For 7 Nights US $1,294
1948.27 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $507/Night
For 7 Nights US $3,547
1100 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $396/Night
For 7 Nights US $2,771
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 Bridgewater
Woodstock
Cavendish
Quechee
Plymouth
Chester
Chester Depot
Proctorsville
Weston
West Windsor
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!
- Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"
- Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
- Quiet Vermont Winter Getaway
- "The Crooked House" with A/C and sauna on private wooded lot near Killington
- Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
- 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
2. How many Accommodations are available in Windsor County?
Currently, the total number of properties listed by RBO in 2026 is over 1470 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
904.17 ft²
7 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- Parking
- Internet
US $250/Night
For 7 Nights US $1,752
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $244/Night
For 7 Nights US $1,707
1574 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $466/Night
For 7 Nights US $3,261
800 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $124/Night
For 7 Nights US $870
1200 ft²
8 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $409/Night
For 7 Nights US $2,862
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $207/Night
For 7 Nights US $1,450
540 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $352/Night
For 7 Nights US $2,461
1085 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Hot Tub
- Spa
US $294/Night
For 7 Nights US $2,056
1500 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $275/Night
For 7 Nights US $1,928
1400 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $424/Night
For 7 Nights US $2,971
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $191/Night
For 7 Nights US $1,339
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $250/Night
For 7 Nights US $1,752
