Vacation Homes in Windsor County, VT
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Top cities with Vacation Homes to explore in Windsor County

Ludlow
Top Vacation Homes in Windsor County

Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
Find the Best Vacation Homes in Windsor County
Why book a vacation home in Windsor County?
Vacation homes in Windsor County make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Windsor County?
Private Windsor County rental homes range between $888 - $888 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Windsor County vacation home rentals. You might look for Windsor County rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Windsor County offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Windsor County?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Windsor County. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Windsor County hotels and vacation homes that best suit your stay. We also have deals for flights, and Windsor County car rentals. You’ll save even more when you bundle your items into a Windsor County vacation package!
How many vacation homes are available to book in Windsor County?
There are 444 rental homes in Windsor County. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Windsor County?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Windsor County Vacation Homes essential information
Accommodation | 444 Vacation Homes |
|---|---|
Lowest Price | $888 |
Highest Price | $888 |
Popular accommodation | Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Rustic home with a private hot tub, fireplace, cable, & washer/dryer, Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock, Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola, Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!, PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC., Lakefront house with skiing nearby, dock, and amazing views - dog-friendly, Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE, Walk to Trails & Village +Pets - Highland Cabin, New Ludlow Village Home with Stunning Okemo Mountain View |
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