
Vacation Rentals in Windsor County
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Top Cities in Windsor County

Ludlow
Our top choices for Windsor County vacation rentals

Addie's Place: A Quiet and Quirky Guesthouse
Addie's Place: A Quiet and Quirky Guesthouse
Treehouse at Wise Pines- NoBo
Treehouse at Wise Pines- NoBo
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Vermont Double Queen Suite | 10 Mins to Killington
Vermont Double Queen Suite | 10 Mins to Killington
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Ski-In/Out condo with patio, mountain views, washer/dryer, & cableFind vacation rentals that suit your style
Top Windsor County Hotel Reviews

Align Inn Vermont
Find out more about Windsor County
Discover your perfect Windsor County vacation rental with Expedia
How many vacation rentals are available in Windsor County?
Expedia has plenty of vacation rentals to choose from in and around Windsor County, so you’re guaranteed to find the right one for you.
How much is a vacation rental in Windsor County?
The selection of Windsor County vacation rentals we have selected for you start as low as $286 per night. Entering your travel dates in the search wizard you might find even better deals!
What type of vacation rental can I get in Windsor County?
Vacation rentals in Windsor County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Windsor County vacation rentals to suit everyone.
Why should I choose a vacation rental in Windsor County?
Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Windsor County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.
How do I find the best deal on a vacation rental in Windsor County?
Find vacation rentals in Windsor County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Windsor County.
What amenities are available in a vacation rental in Windsor County?
The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Windsor County vacation rentals designed to suit every budget and trip type.
When is the best time to stay in a vacation rental in Windsor County?
Everytime is a great time to head to Windsor County! Staying in a Windsor County vacation rentals you will always find lots going on to keep you entertained.
Why book a vacation rental with Expedia?
Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Windsor County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Windsor County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windsor County, you can save even more.
Can I cancel my vacation rental through Expedia?
Yes, you can cancel or change your Windsor County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.
Explore a world of travel with Expedia
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- Vacation Homes in Windsor County
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