Compare Windsor Cabin Rentals

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Featured Cabin Rentals in Windsor

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket MA
Guests staying at this cabin have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Bear Creek Cabin

Bear Creek Cabin

Charlemont MA
$539 nightly
The price is $602 total per night
$602 total
Jul 25 - Jul 26
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Pittsfield MA
At this cabin, guests have access to features like laundry facilities. Friendly staff can provide concierge services, and also offer advice about sightseeing. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

Huntington MA
Guests staying at this cabin have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale MA
$442 nightly
The price is $493 total per night
$493 total
Jul 16 - Jul 17
Total with taxes and fees
Guests staying at this cabin enjoy a hot tub, laundry facilities, and a garden. This smoke-free cabin also has barbecue grills.
Hot Tub
Kitchen
Artist's Camp on Lake Mahkeenac

Artist's Camp on Lake Mahkeenac

Stockbridge MA
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Lakefront House with Stunning Views and Great Room

Lakefront House with Stunning Views and Great Room

Whitingham VT
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Berkshire Mountain Cottage - Spectacular Views of Mount Greylock

Berkshire Mountain Cottage - Spectacular Views of Mount Greylock

Clarksburg MA
At this cabin, guests have access to barbecue grills.
Air conditioning
Parking available
Cozy mountain retreat-25 secluded acres-beautiful foliage views! Dog friendly!

Cozy mountain retreat-25 secluded acres-beautiful foliage views! Dog friendly!

Halifax VT
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
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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

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $145 nightly
    The price is $162 total per night from Jul 16 to Jul 17
    $162 total
    Jul 16 - Jul 17
    Total with taxes and fees
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $170 nightly
    The price is $190 total per night from Jul 22 to Jul 23
    $190 total
    Jul 22 - Jul 23
    Total with taxes and fees
    8.8/10 Excellent! (1,001 reviews)
    The Yankee Inn

    The Yankee Inn

    461 Pittsfield Rd Lenox MA
    $189 nightly
    The price is $211 total per night from Jul 16 to Jul 17
    $211 total
    Jul 16 - Jul 17
    Total with taxes and fees
    9.2/10 Wonderful! (1,016 reviews)

What is the price range for Windsor cabin rentals?


Cabins in Windsor cost from just $162 a night to $602 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 19 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
19 Cabin Rentals
Lowest Price
$162
Highest Price
$602
Popular accommodation
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating, Bear Creek Cabin, A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything, Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7., Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere, Artist's Camp on Lake Mahkeenac, Lakefront House with Stunning Views and Great Room, Berkshire Mountain Cottage - Spectacular Views of Mount Greylock, Cozy mountain retreat-25 secluded acres-beautiful foliage views! Dog friendly!

More to Explore