West Windsor, Vermont Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in West Windsor, Vermont on RentalSaver.com!

West Windsor Rentals

From $799 per night (USD)
VRBO
Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Place of Peace and Quiet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $799 per night (USD)
VRBO
From $131 per night (USD)
Expedia
Mount Ascutney 1 Bedroom in Brownsville Vermont an IHG Holiday Inn Club Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in the quiet community of Brownsville within West Windsor is our charming mountainside retreat, Mount Ascutney R ...
From $131 per night (USD)
Expedia
From $83 per night (USD)
VRBO
Mount Ascutney Resort in Beautiful Brownsville Vermont Amazing 1 Bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in the quiet community of Brownsville within West Windsor is our charming mountainside retreat, Mount Ascutney R ...
From $83 per night (USD)
VRBO
From $605 per night (USD)
Expedia
Skyhawk Cabin: refined modern getaway with hot tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Skyhawk Cabin! Our Vermont getaway has been completely renovated to offer a curated experience throughout: a ...
From $605 per night (USD)
Expedia
From $266 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 $266 per night (USD)
VRBO
From $238 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 $238 per night (USD)
VRBO
From $205 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 $205 per night (USD)
VRBO
From $232 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 $232 per night (USD)
VRBO
From $392 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 $392 per night (USD)
VRBO
From $461 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 $461 per night (USD)
VRBO
From $334 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 $334 per night (USD)
VRBO
From $433 per night (USD)
Expedia
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 $433 per night (USD)
Expedia
From $229 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 $229 per night (USD)
VRBO
From $196 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 $196 per night (USD)
VRBO
From $210 per night (USD)
VRBO
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 $210 per night (USD)
VRBO
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Expedia
Dog-friendly, 2-story condo at the base of Ascutney with fireplace & balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Mountain's Edge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
Expedia
From $511 per night (USD)
VRBO
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 $511 per night (USD)
VRBO
From $473 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 $473 per night (USD)
Expedia
From $595 per night (USD)
VRBO
Private house & cottage, pond, mountain view, balcony, outdoor dining, fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Auger Hole Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $595 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Red Barn Cabin
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our cozy modern cabin is anything but ordinary, nestled amidst the pastoral landscapes of Brownsville, Vermont. Moments ...
From $238 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Ski-in/out, dog-friendly condo with prime location for skiing & hiking
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Ascutney Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $396 per night (USD)
VRBO
From $851 per night (USD)
Expedia
Cloudborne Cabin: 22 acres of luxury by Woodstock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to our custom-built luxury retreat in the heart of VT on 22 acres! Our enchanting 3-bed, 3.5-bathouse is tailor- ...
From $851 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Rock Haven Sugar House - Field and 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 ch ...
From $271 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Luxury Home, Dog Suite - Rock Haven Carriage House
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 Thin ...
From $438 per night (USD)
Expedia
From $621 per night (USD)
VRBO
Cozy Modern Cabin w/ Hot Tub & Beautiful View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Plan a relaxing escape to this cozy & contemporary-outfitted cabin w/ an unparalleled mountain view! Just an eight-minu ...
From $621 per night (USD)
VRBO
From $160 per night (USD)
VRBO
Enjoy snowball fights or romantic nights in a 1BD vacation apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Make some memories at this unique and family-friendly pA Beautiful Mountainside Escape Vacationing in Vermont brings ...
From $160 per night (USD)
VRBO
From $346 per night (USD)
VRBO
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 $346 per night (USD)
VRBO
From $824 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 $824 per night (USD)
VRBO
From $242 per night (USD)
VRBO
Romantic Getaway or Family winter adventures in 2BD w/resort activities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A Beautiful Mountainside Escape Vacationing in Vermont brings a lot of things to mind: apple picking, maple syrup tas ...
From $242 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Modern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up to sweeping Vermont views from this designer-built Mt. Ascutney cabin — with fire pit, chef’s kitchen, and cozy ...
From $408 per night (USD)
Expedia
From $300 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 $300 per night (USD)
VRBO
From $1544 per night (USD)
VRBO
The BARN at Reading Farms Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Long term rental discounts available .The BARN at Reading Farms Estate is one of the outbuildings on the Estate. The BAR ...
From $1544 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Stunning Modern Cabin on Beautiful Vermont Farm
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $403 per night (USD)
VRBO
From $517 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $517 per night (USD)
VRBO
From $252 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 $252 per night (USD)
VRBO
From $1430 per night (USD)
VRBO
Guest wing on a 400 private acre estate. Sleeps 8
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Come and enjoy a stay in beautiful Vermont! The 30,000 square foot estate is now available for smaller groups. Enjoy al ...
From $1430 per night (USD)
VRBO
From $935 per night (USD)
VRBO
The Cottage on private gated 400 acre Reading Farms Estate
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
This home is one of 3 on a 400 gated acre estate . It has a kitchen, 3 bedroom, 1.5 bathrooms. Main floor bedroom has a ...
From $935 per night (USD)
VRBO
From $4261 per night (USD)
VRBO
Reading Farms Estate
Bedrooms:
13
Bathrooms:
15
Sleeps:
46
** 2026 season 1 week stay special pricing $19,750** please inquire **.Reading Farms Estate is an elevated lifesty ...
From $4261 per night (USD)
VRBO
From $401 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $401 per night (USD)
VRBO
From $517 per night (USD)
VRBO
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $517 per night (USD)
VRBO
From $455 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $455 per night (USD)
VRBO

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West Windsor Rentals

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Results: 41 Rentals