Windsor Rentals
- From $225 per night (USD)
VRBO
Vermont cabin on 20 acres in open field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Long lasting Sunsets are what this cabin is all about. As well as swimming in the pond and nearby brook. Hiking mt. ascu ...
From $225 per night (USD)VRBO
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VRBO
Largest Colonial Revival Mansion less than 15 minutes to Woodstock
- Bedrooms:
- 15
- Bathrooms:
- 15
- Sleeps:
- 32
Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of ...
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VRBO
Private wing of the Largest Colonial Revival Mansion in the US
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of ...
Click For PricingVRBO
- From $3554 per night (USD)
VRBO
Totally Restored Grand Mansion & Estate overlooking the CT River
- Bedrooms:
- 19
- Bathrooms:
- 16
- Sleeps:
- 39
Perched atop Juniper Hill, the Windsor Mansion Inn spans over 14 acres in the historic hamlet of Windsor, Vermont, the t ...
From $3554 per night (USD)VRBO
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VRBO
Private Wing of largest Colonial Revival Mansion- Only 15 min to Woodstock
- Bedrooms:
- 0
- Bathrooms:
- 3
- Sleeps:
- 7
Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of ...
Click For PricingVRBO
- From $150 per night (USD)
Expedia
Child-friendly home near athletic courts & beach access - firepit, AC, and W\/D
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summit House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $150 per night (USD)Expedia
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VRBO
Kennedy’s House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Feel the relaxation of Vermont living within a few steps to Kennedy Pond; all of its amenities and beach. Don’t forget ...
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- From $235 per night (USD)
VRBO
Lovely Vermont Cabin on a quiet street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Private cabin with in the heart of Central Valley, close to State park, Connecticut River and a few ski resorts. Private ...
From $235 per night (USD)VRBO
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VRBO
Holiday Inn Club Vacation Resort, an IHG Property - 3BD\/3BA at Mount Ascutney
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
From the Mt. Ascutney resort, you are within driving distance of three well-known ski resorts - , Okemo (34 mins), and M ...
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- From $363 per night (USD)
VRBO
Log Cabin home with Mt Ascutney views and pool table
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
This home is located on the slopes of Mt. Ascutney, within walking distance from Mt. Ascutney Resort, the hotel, restaur ...
From $363 per night (USD)VRBO
- From $284 per night (USD)
VRBO
Villa Near Biking and Hiking Trails
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This villa is perfect for your group! Enjoy stunning views from the top of Mt. Ascutney State Park right outside your do ...
From $284 per night (USD)VRBO
- From $298 per night (USD)
VRBO
Villa with Pool + Fitness Center Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic loc ...
From $298 per night (USD)VRBO
- From $237 per night (USD)
VRBO
Vermont Villa Near the Trails
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in ...
From $237 per night (USD)VRBO
- From $284 per night (USD)
VRBO
Villa with a Fireplace Near the Trails
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Dreaming of a cozy villa with a fireplace? You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Pa ...
From $284 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Exquisite Log Home with views near Woodstock, Vermont
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This beautiful Vermont log home is for rent for all seasons. It contains 4 bedrooms, 3 bathrooms, a gourmet kitchen with ...
From $375 per night (USD)VRBO
- From $154 per night (USD)
Expedia
Dog-friendly, 2-story condo at the base of Ascutney with fireplace & balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Mountain's Edge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $154 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Inviting Vermont Cabin On Mount Ascutney!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Bundle up for alpine activities or curl up and get cozy at this 4-bedroom, 2-bath home. Situated just a short walk from ...
From $340 per night (USD)VRBO
- From $265 per night (USD)
Expedia
Private mountain setting w\/ open rooms, hiking, biking, skiing at your doorstep!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Enjoy our modern house with inspiring mountain views, large galley kitchen w/ dining area, 2 car attached garage, large ...
From $265 per night (USD)Expedia
- From $185 per night (USD)
VRBO
Ski-in\/out, dog-friendly condo with prime location for skiing & hiking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Ascutney Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $185 per night (USD)VRBO
- From $312 per night (USD)
Expedia
Secluded dog-friendly home near ski resorts with mtn views, fireplace, foosball
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Alpine Bliss Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $312 per night (USD)Expedia
- From $614 per night (USD)
VRBO
Luxury Vermont Vacation Rental: Private Hot Tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Your mountain escape awaits at this spacious vacation home in West Windsor, VT! Adorned with wood paneling, cathedral ce ...
From $614 per night (USD)VRBO
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VRBO
Romantic Getaway or Family winter adventures in 2BD w\/resort activities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: A Beautiful Mountainside Escape Vacationing in Vermont brings a lot of things to mind: apple picking, maple sy ...
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Expedia
Magnificent mountain cottage with deck, firepit, W\/D, wood stove, & water views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage Under The Mountain Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
Click For PricingExpedia
- From $329 per night (USD)
VRBO
4 Bedroom Home Convenient to the Upper Valley, Ski Resorts, and VAST Trails.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to The Hollow! This 4 bedroom/2 bathroom home is the perfect place to launch an adventure or to relax and gathe ...
From $329 per night (USD)VRBO
- From $260 per night (USD)
VRBO
Enjoy snowball fights or romantic nights in a 1BD vacation apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: A Beautiful Mountainside Escape Vacationing in Vermont brings a lot of things to mind: apple picking, maple sy ...
From $260 per night (USD)VRBO
- From $235 per night (USD)
VRBO
Lovely 2 Bedroom Townhouse on Ascutney Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a fun outdoor adventure at this at this centrally-located condo. Ascutney trails are just outside the door, with m ...
From $235 per night (USD)VRBO