West Windsor Rentals
From $521 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 $521 per night (USD)VRBO
From $318 per night (USD)VRBO
Meadow View- 35 Acres outside your door
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly renovated in 2025! Meadow View is your home away from home. 35 acres at your fingertips including 2 trout ponds an ...
From $318 per night (USD)VRBO
From $218 per night (USD)VRBO
Sunset Cabin - your private romantic hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; ...
From $218 per night (USD)VRBO
From $267 per night (USD)Expedia
Cozy Historic Hilltop Cottage with Mount Ascutney View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This exceedingly charming cottage on a wooded hilltop just outside of Brownsville has great views of Mt Ascutney and a b ...
From $267 per night (USD)Expedia
From $571 per night (USD)VRBO
Long Range Mountain Views in West Windsor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Thistle Hill, a beautiful private property on 17 acres. Home is located 12 miles from Woodstock in the heart ...
From $571 per night (USD)VRBO
From $155 per night (USD)VRBO
Enjoy snowball fights or romantic nights in a 1BD vacation apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Make some memories at this unique and family-friendly pA Beautiful Mountainside Escape Vacationing in Vermont brings a ...
From $155 per night (USD)VRBO
From $409 per night (USD)VRBO
Beautiful craftsman-built home with natural wood and large windows in every room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located on a quiet road approximately one mile from the center of Brownsville, the property is a short drive from Woodst ...
From $409 per night (USD)VRBO
From $283 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 $283 per night (USD)VRBO
From $290 per night (USD)VRBO
Villa with Games Room + 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 $290 per night (USD)VRBO
From $176 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 $176 per night (USD)VRBO
From $229 per night (USD)VRBO
2-Bedroom Villa w/ King, Queen & Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Set among the forested hills of southern Vermont, this two-bedroom villa is the perfect mountain escape for families and ...
From $229 per night (USD)VRBO
From $600 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 $600 per night (USD)VRBO
From $436 per night (USD)VRBO
Sweeping Vermont Views From A Private, Designer, Ascutney Cabin
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Combining views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom c ...
From $436 per night (USD)VRBO
From $643 per night (USD)Expedia
Inviting Vermont Home On Mount Ascutney!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Whether you're bundling up for alpine adventures or unwinding in style, this freshly updated 3-bed, 2-bath Windsor retre ...
From $643 per night (USD)Expedia
From $987 per night (USD)VRBO
Luxury Vermont Vacation Rental: Private Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Your mountain escape awaits at this spacious vacation home in West Windsor, VT! Adorned with wood paneling, cathedral ce ...
From $987 per night (USD)VRBO
From $347 per night (USD)Expedia
Rock Haven Sugar House on a Working Farm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Nestled in the serene beauty of Reading, Vermont, the Rock Haven Sugar House offers a unique blend of rustic c ...
From $347 per night (USD)Expedia
From $446 per night (USD)VRBO
Carriage House with Valley Views, Rock Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This stay is a true Vermont Gem, offering a perfect blend of luxury and natural beauty. Please see: Other T ...
From $446 per night (USD)VRBO
From $408 per night (USD)Expedia
Antique farmhouse with spectacular mountain view in a bucolic setting.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in West Windsor, this charming farmhouse, built in 1842 with some of the original floors, offers 4 spacious bedr ...
From $408 per night (USD)Expedia
From $167 per night (USD)VRBO
By the Month, Charming Guest Suite in Reading, Vermont
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay comfortably in Reading/West Windsor, Vermont at this charming farmhouse. This two story guest suite offers a pleasa ...
From $167 per night (USD)VRBO
From $527 per night (USD)Expedia
Cabin on the hill Ascutney Vt - 4 bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Nestled in the serene woods of Brownsville Vermont, this charming cabin offers a perfect retreat from everyday life. The ...
From $527 per night (USD)Expedia
From $799 per night (USD)VRBO
The Gathering House at Mount Ascutney
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
It might be your perfect Vermont getaway! Relax, recharge, and take in the beauty of Vermont’s mountains. This beautiful ...
From $799 per night (USD)VRBO
From $397 per night (USD)Expedia
Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ascutney Lofts offers modern, serene retreats nestled in the heart of Vermont’s natural beauty. Thoughtfully designed wi ...
From $397 per night (USD)Expedia
From $397 per night (USD)VRBO
Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ascutney Lofts offers modern, serene retreats nestled in the heart of Vermont’s natural beauty. Thoughtfully designed wi ...
From $397 per night (USD)VRBO
From $397 per night (USD)Expedia
Luxury Loft With Solo Fire Pit & Trails Close to Okemo & Ascutney EV Charger
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ascutney Lofts offers modern, serene retreats nestled in the heart of Vermont’s natural beauty. Thoughtfully designed wi ...
From $397 per night (USD)Expedia
From $402 per night (USD)VRBO
High-End Loft - Cozy Firepit, Hiking and Biking Trails, Near Okemo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ascutney Lofts offers modern, serene retreats nestled in the heart of Vermont’s natural beauty. Thoughtfully designed wi ...
From $402 per night (USD)VRBO
From $397 per night (USD)Expedia
Designer Cabin With Solo Firepit Near Ski Trails - Ascutney Lofts
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ascutney Lofts offers modern, serene retreats nestled in the heart of Vermont’s natural beauty. Thoughtfully designed wi ...
From $397 per night (USD)Expedia
From $371 per night (USD)VRBO
Ski-in/out condo with prime location for skiing & hiking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Enviably situated in a ski-in/out position at the base of Mt. Ascutney, this two-story condo is a place for Vermont adve ...
From $371 per night (USD)VRBO
From $830 per night (USD)Expedia
Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Tucked away in the peaceful forests of Vermont, this spacious and fully equipped getaway offers the perfect blend of com ...
From $830 per night (USD)Expedia
From $804 per night (USD)VRBO
Skyhawk Cabin: refined modern getaway with hot tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Skyhawk Cabin! Our Vermont getaway has been completely renovated to offer a curated experience t ...
From $804 per night (USD)VRBO