Compare Cheshire Cabin Rentals

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Featured Cheshire Cabins

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Stephentown NY
$263 nightly
The price is $292 total per night
$292 total
Jan 30 - Jan 31
Total with taxes and fees
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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

Hinsdale MA
$390 nightly
The price is $435 total per night
$435 total
Jan 4 - Jan 5
Total with taxes and fees
Guests staying at this cabin enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cabin also has a garden.
Bear Creek Cabin

Bear Creek Cabin

Charlemont MA
$539 nightly
The price is $602 total per night
$602 total
Jan 6 - Jan 7
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
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
Dadzpad Cabin in Stephentown

Dadzpad Cabin in Stephentown

Stephentown NY
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake NY
$165 nightly
The price is $183 total per night
$183 total
Jan 3 - Jan 4
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Washer
Dryer
Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience

Sand Lake NY
$165 nightly
The price is $183 total per night
$183 total
Jan 3 - Jan 4
Total with taxes and fees
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

Averill Park NY
$975 nightly
The price is $1,083 total per night
$1,083 total
Jan 4 - Jan 5
Total with taxes and fees
At this cabin, guests have access to barbecue grills. Staff members can answer questions about accommodations, and also provide concierge services.
Kitchen
Pet friendly
Artist's Camp on Lake Mahkeenac

Artist's Camp on Lake Mahkeenac

Stockbridge MA
Guests staying at this cabin have access to laundry facilities, a garden, and barbecue grills.
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 Cheshire

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $126 nightly
    The price is $141 total per night from Jan 4 to Jan 5
    $141 total
    Jan 4 - Jan 5
    Total with taxes and fees
    8.6/10 Excellent! (2,195 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $116 nightly
    The price is $130 total per night from Feb 2 to Feb 3
    $130 total
    Feb 2 - Feb 3
    Total with taxes and fees
    8.6/10 Excellent! (1,002 reviews)
    The Williams Inn

    The Williams Inn

    101 Spring Street Williamstown MA
    $186 nightly
    The price is $208 total per night from Jan 11 to Jan 12
    $208 total
    Jan 11 - Jan 12
    Total with taxes and fees
    9.6/10 Exceptional! (557 reviews)

What is the price range for Cheshire cabin rentals?


Cabins in Cheshire cost from just $130 a night to $1,083 a night for that something truly special. Prices and availability are subject to change. Additional terms may apply.

What types of Cheshire 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 26 unique Cheshire cabins to choose from, your perfect escape is just a click away.


How do I find cheap cabin rentals in Cheshire?


To see the latest deals on Cheshire 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 Cheshire 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 Cheshire 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 Cheshire that deliver those special extras that make all the difference.


How do I find pet-friendly cabins in Cheshire?


Click on our pet-friendly filter for woof-tastic Cheshire 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 Cheshire?


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 Cheshire on Orbitz?


Enter your travel details, hit search, and use the filters to see our best deals on cabins in Cheshire. 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.


Cheshire Cabin Rentals essential information

Accommodation
26 Cabin Rentals
Lowest Price
$130
Highest Price
$1,083
Popular accommodation
Charming 3-bedroom Cabin for nature lovers, Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere, Bear Creek Cabin, Lakefront House with Stunning Views and Great Room, Dadzpad Cabin in Stephentown, Taborton Harvest Boulder Pines Cabin in the woods, Taborton Harvest Timber Trails Unique cabin experience, A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!, Artist's Camp on Lake Mahkeenac

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