Compare Cheshire Cottage Rentals

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Featured Cheshire Cottages

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2 out of 5
Guests staying at this cottage can enjoy a gym, barbecue grills, and a garden.
Kitchen
Pet friendly
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

This cottage features free WiFi in public areas and a garden.
Kitchen
Free WiFi
Charlemont Retreat on Chickley River w/ EV Charger

Charlemont Retreat on Chickley River w/ EV Charger

3 out of 5
This cottage features free WiFi in public areas and barbecue grills. You can take advantage of free offsite parking if you drive.
Kitchen
Washer
Entire cottage in Berkshire Villiage

Entire cottage in Berkshire Villiage

3 out of 5
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres

2 out of 5
$1,565 nightly
The price is $1,588 total per night
$1,588 total
Oct 16 - Oct 17
Total with taxes and fees
Guests of Berkshires farm, 30+ guests, 50 acres enjoy a hot tub, an arcade/game room, and laundry facilities. Additional amenities include a garden and barbecue grills.
Hot Tub
Kitchen
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

At this vacation home, guests have access to barbecue grills.
Kitchen
Pet friendly
A-frame Cabin w/ Furnished Deck in Becket!

A-frame Cabin w/ Furnished Deck in Becket!

3 out of 5
This cottage features free WiFi in public areas and barbecue grills. Free parking is included with your stay.
Kitchen
Pet friendly
Plan your Berkshires by the lake

Plan your Berkshires by the lake

Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
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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

    Harbour House Inn

    Harbour House Inn

    725 North State Road, Cheshire, MA
    $262 nightly
    The price is $277 total per night from Oct 14 to Oct 15
    $277 total
    Oct 14 - Oct 15
    Total with taxes and fees
    9.6/10 Exceptional! (38 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $112 nightly
    The price is $125 total per night from Nov 2 to Nov 3
    $125 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.6/10 Excellent! (2,039 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! (678 reviews)

Cottages

Book a cottage in Cheshire
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Cheshire. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Cheshire better.

Cottage apartments in Cheshire range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Cheshire
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Cheshire and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Cheshire cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Cheshire. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Cheshire Cottages essential information

Accommodation
77 Cottages
Lowest Price
$125
Highest Price
$1,588
Popular accommodation
The Clearing - Quiet - Close To Nature, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Charming historic cottage on scenic road to Mt. Greylock, Charlemont Retreat on Chickley River w/ EV Charger, Entire cottage in Berkshire Villiage, Berkshires farm, 30+ guests, 50 acres, Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location, A-frame Cabin w/ Furnished Deck in Becket!, Plan your Berkshires by the lake

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