Compare Windsor Cabin Rentals

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Featured Windsor Cabins

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
3387 East Mountain Road Killington VT
Renovated in 2023, Ski in & out Spruce Glen Townhomes on Great Eastern Trail offers ski-in/ski-out access, a sauna, and free WiFi in public areas. A stay here includes free parking. Other amenities at this ski cabin include express check-out and laundry facilities.
Kitchen
Washer
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Ludlow VT
At this cabin, guests have access to features like laundry facilities. This cabin also has barbecue grills.
Kitchen
Washer
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Mount Holly VT
Guests staying at this cabin enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cabin also has a garden.
Hot Tub
Kitchen
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12

Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12

Ludlow VT
At this cabin, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly cabin also has a garden.
Kitchen
Washer
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton VT
The price is $355 total per night
$355 total
per night
Nov 24 - Nov 25
Guests staying at this cabin have access to a garden and barbecue grills.
Kitchen
Pet friendly
The Cabin that brings people together

The Cabin that brings people together

Bridgewater VT
Guests staying at this cabin enjoy ski-in/ski-out access, a hot tub, and an arcade/game room. Other amenities at this ski cabin include laundry facilities, barbecue grills, and a garden.
Hot Tub
Kitchen
Amazing home on 90 acres - AC, fireplace & great mountain views

Amazing home on 90 acres - AC, fireplace & great mountain views

At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF

SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF

Mount Holly VT
At this cabin, guests have access to barbecue grills.
Kitchen
Pet friendly
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi

Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi

Ludlow VT
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
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See all available properties in Windsor
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Windsor

    Fat Sheep Farm & Cabins

    Fat Sheep Farm & Cabins

    122 Best Rd Windsor VT
    $193 nightly
    The price is $211 total per night from Dec 7 to Dec 8
    $211 total
    Dec 7 - Dec 8
    Total with taxes and fees
    9.6/10 Exceptional! (12 reviews)
    Killington Mountain Lodge, Tapestry Collection by Hilton

    Killington Mountain Lodge, Tapestry Collection by Hilton

    2617 Killington Rd Killington VT
    $147 nightly
    The price is $161 total per night from Nov 25 to Nov 26
    $161 total
    Nov 25 - Nov 26
    Total with taxes and fees
    7.2/10 Good! (1,000 reviews)
    Woodstock Inn & Resort

    Woodstock Inn & Resort

    Fourteen The Green Woodstock VT
    $369 nightly
    The price is $406 total per night from Nov 30 to Dec 1
    $406 total
    Nov 30 - Dec 1
    Total with taxes and fees
    9.2/10 Wonderful! (549 reviews)

What is the price range for Windsor cabin rentals?


Cabins in Windsor cost from just $161 a night to $406 a night for that something truly special. Prices and availability are subject to change. Additional terms may apply.

What types of Windsor cabin are available?


You might fancy a luxury log cabin retreat for a romantic getaway. Maybe you’re after a family lodge in the woods or a rustic hideaway by the water. With a fantastic selection of 91 unique Windsor cabins to choose from, your perfect escape is just a click away.


How do I find cheap cabin rentals in Windsor?


To see the latest deals on Windsor cabins rentals, enter your travel details and hit search. Arrange your results by price to see the cheapest options first and use the budget filter, map, and ratings to compare cabins. We find prices are often lower during , so this could be the best time to find a cabin bargain.


Why should I choose a Windsor cabin rental?


Picture a cozy space full of personality, space, and privacy. A cabin booked through Orbitz is a place where you can escape the rat race, unwind, and make plans on your private deck, cocooned by trees, water, or views for days. Cook for yourself, just as you like it, share special moments, and build memories.






What amenities will I find in Windsor cabins?


Sink into your outdoor hot tub in a secluded cabin rental or let the kids splash around in a cabin resort’s indoor pool. Our amenities filters make it easy to find cabins in Windsor that deliver those special extras that make all the difference.


How do I find pet-friendly cabins in Windsor?


Click on our pet-friendly filter for woof-tastic Windsor cabins rentals, where your pooch can enjoy a vacation, too. Take walks to dog-happy cafés, explore nature together from sunrise to sundown, then snuggle together in front of a cozy log fire or under the twinkling stars on your deck.


Are there any luxury cabin rentals in Windsor?


To find those luxury cabins with the top-notch touches you’re looking for, use the budget filter, read customer reviews, and dip into the property listings for the details. You can then compare cabins and choose the best cabins for a truly luxurious experience.


How do I find some of the best cabins in Windsor on Orbitz?


Enter your travel details, hit search, and use the filters to see our best deals on cabins in Windsor. Easy! From luxury log cabin rentals to affordable weekend cabin getaways, Orbitz finds your dream cabin in just a few clicks. You can unlock Orbucks when you sign up for Orbitz RewardsOpens in a new window, too.


Windsor Cabin Rentals essential information

Accommodation
91 Cabin Rentals
Lowest Price
$161
Highest Price
$406
Popular accommodation
Ski in & out Spruce Glen Townhomes on Great Eastern Trail, Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore, Cozy Hideaway near Ludlow/Okemo. HOT TUB!!, Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12, Charming Fully Renovated One-Room Schoolhouse on 22+ acres, The Cabin that brings people together, Amazing home on 90 acres - AC, fireplace & great mountain views, SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF, Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi

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