Compare Cheshire Cottage Rentals

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Featured Cheshire Cottages

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

Cummington MA
At this cottage, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

3 out of 5
Charlemont MA
This cottage features free WiFi in public areas and barbecue grills. If you plan to drive, free offsite parking is available.
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
Canaan NY
Guests staying at this cottage can enjoy a gym, barbecue grills, and a garden.
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro MA
This cottage features free WiFi in public areas and a garden.
Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill

3 out of 5
Windsor MA
This cottage features free WiFi in public areas and barbecue grills. Free parking is included with your stay. This smoke-free cottage also has a garden.
Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres

2 out of 5
New Lebanon NY
$1,822 nightly
The price is $1,847 total per night
$1,847 total
Jan 26 - Jan 27
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.
Charlemont Retreat on Chickley River w/ EV Charger

Charlemont Retreat on Chickley River w/ EV Charger

3 out of 5
Charlemont MA
This cottage features free WiFi in public areas and barbecue grills. You can take advantage of free offsite parking if you drive.
Luxury Vacation Rental in the Berkshires!

Luxury Vacation Rental in the Berkshires!

3 out of 5
Williamstown MA
This cottage features free WiFi in public areas and barbecue grills. There's free parking if you drive.
Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, walking distance to lake

Averill Park NY
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
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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! (2,182 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $121 nightly
    The price is $135 total per night from Feb 1 to Feb 2
    $135 total
    Feb 1 - Feb 2
    Total with taxes and fees
    8.6/10 Excellent! (1,000 reviews)
    The Williams Inn

    The Williams Inn

    101 Spring Street Williamstown MA
    $175 nightly
    The price is $196 total per night from Jan 11 to Jan 12
    $196 total
    Jan 11 - Jan 12
    Total with taxes and fees
    9.6/10 Exceptional! (554 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
80 Cottages
Lowest Price
$135
Highest Price
$1,847
Popular accommodation
The Clearing - Quiet - Close To Nature, Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Charming historic cottage on scenic road to Mt. Greylock, Massachusetts Vacation Rental w/ Deck & Grill, Berkshires farm, 30+ guests, 50 acres, Charlemont Retreat on Chickley River w/ EV Charger, Luxury Vacation Rental in the Berkshires!, Cozy cottage with pool, walking distance to lake

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