- USA
- Vermont
- Windsor County
- Winter Rental
Windsor County Winter Rentals & Holiday Homes
Discover winter rentals Windsor County - We found 1968 exact matches
- Parking
- TV
- Security/Safety
- Security/Safety
- Sports/Activities
- Skiing
- Pool
- TV
- View
- Pet Friendly
- Security/Safety
- Bedding/Linens
- Pet Friendly
- Wheelchair Accessible
- Balcony/Terrace
- Parking
- Pet Friendly
- TV
- Pet Friendly
- View
- Private Beach
- TV
- Balcony/Terrace
- Security/Safety
- Pet Friendly
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Pet Friendly
- Security/Safety
- Sports/Activities
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Security/Safety
- Bedding/Linens
- Wellness Facilities
- Parking
- TV
- Balcony/Terrace
- Parking
- Pet Friendly
- TV
- Parking
- TV
- Security/Safety
- Pet Friendly
- TV
- Security/Safety
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
About Windsor County Winter Rental on Rent By Owner
Planning on a winter vacation in Windsor County? Discover 1968 places to stay in Windsor County, for those traveling with their family, friends, in groups, or for a wedding retreat.
At Rent By Owner, we have a wide range of listings for accommodations in Windsor County, VT that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. RBO winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Windsor County winter accommodation starts at AU $890, and the most popular properties in Windsor County are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, RBO will make your winter trip memorable.
Rent By Owner offers a great deal for travelers planning on renting a place in Windsor County, to enjoy these benefits and to book your winter vacation homes, go to RBO filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Windsor County and unlock even more amazing deals.
Frequently Asked Questions About Windsor County Winter Rentals
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 Winter Rentals in Windsor County:
- Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Luxurious, Secluded, Ski Chalet, w/Country Decor & Hot Tub Near Okemo
- Charming Log Cabin Apartment in Woodstock Village
- GORGEOUS LAKEFRONT - Autumn Splendor - Private Setting - 5 Mins to Okemo!
- Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"
- Quiet Vermont Winter Getaway
- Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
- "The Crooked House" with A/C and sauna on private wooded lot near Killington
- Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
- 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
- Central 4-Bedroom Mountain Escape–1 Minute drive to Slopes & Walk to Main St
- 375 Hawk Spur
- SKI In/SKI Out. 4 Bedrooms, A1- Walk to Pool/Gym, End unit with tons of sunlight
- 15 min to Killington & Okemo 4-bedroom Chalet w/Private Sauna & Hot Tub
See all pet-friendly vacation rentals in Windsor County on Rent By Owner
