Compare Cheshire Cabin Rentals

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Featured Cheshire Cabins

Florida Mountain Log Cabin!

Florida Mountain Log Cabin!

2 out of 5
$409 nightly
The price is $432 total per night
$432 total
Oct 23 - Oct 24
Total with taxes and fees
At this cabin, guests have access to barbecue grills.
Kitchen
Air conditioning
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly

The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly

$451 nightly
The price is $477 total per night
$477 total
Oct 20 - Oct 21
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 Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

$165 nightly
The price is $183 total per night
$183 total
Oct 5 - Oct 6
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
Bear Creek Cabin

Bear Creek Cabin

$527 nightly
The price is $589 total per night
$589 total
Oct 7 - Oct 8
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
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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

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
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

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
Berkshire Mountain Cottage - Spectacular Views of Mount Greylock

Berkshire Mountain Cottage - Spectacular Views of Mount Greylock

At this vacation home, guests have access to barbecue grills.
Air conditioning
Parking available
Lakefront House with Stunning Views and Great Room

Lakefront House with Stunning Views and Great Room

Guests staying at this cabin have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Artist's Camp on Lake Mahkeenac

Artist's Camp on Lake Mahkeenac

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 Cheshire

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $98 nightly
    The price is $110 total per night from Oct 5 to Oct 6
    $110 total
    Oct 5 - Oct 6
    Total with taxes and fees
    8.6/10 Excellent! (2,028 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    $113 nightly
    The price is $126 total per night from Nov 2 to Nov 3
    $126 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (668 reviews)
    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    190 Meadow Street, South Lee, MA
    $129 nightly
    The price is $144 total per night from Nov 2 to Nov 3
    $144 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9/10 Wonderful! (741 reviews)

What is the price range for Cheshire cabin rentals?


Cabins in Cheshire cost from just $110 a night to $589 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 29 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
29 Cabin Rentals
Lowest Price
$110
Highest Price
$589
Popular accommodation
Florida Mountain Log Cabin!, The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly, Taborton Harvest Boulder Pines Cabin in the woods, Bear Creek Cabin, Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere, A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything, Berkshire Mountain Cottage - Spectacular Views of Mount Greylock, Lakefront House with Stunning Views and Great Room, Artist's Camp on Lake Mahkeenac

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