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Our top choices for Cheshire cottages
1. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck3.0 star property
Stephentown
The price is CA $359
CA $359
CA $830 total
includes taxes & fees
Nov 8 - Nov 9
2. The Cottage on Mill Brook is walking distance to Berkshire East and the River.
The Cottage on Mill Brook is walking distance to Berkshire East and the River.Charlemont
The price is CA $596
CA $596
CA $864 total
includes taxes & fees
Nov 8 - Nov 9
3. Berkshires farm, 30+ guests, 50 acres
Berkshires farm, 30+ guests, 50 acresNew Lebanon
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
The price is CA $1,327
CA $1,327
CA $2,646 total
includes taxes & fees
Dec 1 - Dec 2
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.
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.
Learn more about Cheshire
Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.
Top reviews in Cheshire
The Williams Inn
The Williams InnWilliamstown
10/10 Excellent
Nice hotel, good location
Large rooms
But noisy aircon
Nice hotel, good location
Large rooms
But noisy aircon
peter
Hotel On North
Hotel On NorthPittsfield
10/10 Excellent
This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night.
This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night.
alan
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
10/10 Excellent
it was beautiful, centrally located, perfect getaway
it was beautiful, centrally located, perfect getaway
Tara
Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
10/10 Excellent
We enjoyed our stay. Aspects of it
We enjoyed our stay. Aspects of it
Kiril
Maple Terrace Motel
Maple Terrace MotelWilliamstown
10/10 Excellent
The room is clean, well stocked and spacious. Check in was smooth oth and the front desk staff was warm and helpful.
The room is clean, well stocked and spacious. Check in was smooth oth and the front desk staff was warm and helpful.
Tanya
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art HotelAdams
10/10 Excellent
Incredible staff, free parking and cute rooms!
Incredible staff, free parking and cute rooms!
Priscilla
Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
10/10 Excellent
The owners are really generous and friendly! The Breakfast is the best I ever had anywhere I have ever been! All sorts of fruits, yogurts, all kinds of spreads, different types of bread, and all organic. Amazing generosity!
The owners are really generous and friendly! The Breakfast is the best I ever had anywhere I have ever been! All sorts of fruits, yogurts, all kinds of spreads, different types of bread, and all organic. Amazing generosity!
Alexander
Blue Vista Motor Lodge
Blue Vista Motor LodgeNorth Adams
10/10 Excellent
Property is beautiful with breathtaking views !
The fire pits , sauna and hot hubs are a great addition to a great motel !
Early sunrise viewing a must ! North Adams is a great town nearby -
Property is beautiful with breathtaking views !
The fire pits , sauna and hot hubs are a great addition to a great motel !
Early sunrise viewing a must ! North Adams is a great town nearby -
patricia
Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
10/10 Excellent
The property was excellent. They are just finishing renovations so it did quite work for breakfast. But overall when renovations are finished it will be great.loved the coffee
The property was excellent. They are just finishing renovations so it did quite work for breakfast. But overall when renovations are finished it will be great.loved the coffee
Brian
Williamstown Motel
Williamstown MotelWilliamstown
10/10 Excellent
A pleasant surprise. The staff was very friendly and even accepted to change my reservation day. The service at the counter was exceptional. The room was clean, nice bathroom, AC. No complaints.
A pleasant surprise. The staff was very friendly and even accepted to change my reservation day. The service at the counter was exceptional. The room was clean, nice bathroom, AC. No complaints.
Guy
The Yankee Inn
The Yankee InnLenox
10/10 Excellent
Really clean and quiet.. Love!!
Really clean and quiet.. Love!!
Gilles
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
10/10 Excellent
So quiet and very friendly and they went out of there way to make us feel welcome
So quiet and very friendly and they went out of there way to make us feel welcome
Pete
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
10/10 Excellent
Very modern and attractive hotel. Looks like it was recently updated. Friendly staff. Excellent breakfast buffet with good choices. Rooms were modern, clean, comfortable and functional. Highly recommend this place!
Very modern and attractive hotel. Looks like it was recently updated. Friendly staff. Excellent breakfast buffet with good choices. Rooms were modern, clean, comfortable and functional. Highly recommend this place!
Smadar
Cozy Corner Motel
Cozy Corner MotelWilliamstown
10/10 Excellent
Pour le prix, c'est imbattable. Super service, bon petit déjeuner. Je considère le meilleur motel a ce prix.
Pour le prix, c'est imbattable. Super service, bon petit déjeuner. Je considère le meilleur motel a ce prix.
alain
Frequently Asked Questions
How much do cottages in Cheshire cost?
Cottages in Cheshire range between CA $358 and CA $1,326 per night. These properties offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Cheshire with Expedia?
We think that a vacation should be stress-free, so if you're seeking cottages in Cheshire at a great price, Expedia has your back. Save those pennies and stay in an inexpensive option far away from the city rush, or splurge on a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Cheshire?
An excellent way to uncover cheap cottages in Cheshire is with Expedia's handy filter tool. Narrow your search by budget, amenities and star rating to nab excellent rates in a couple of clicks.
What is there to do in Cheshire near my cottage?
If you're eager to see the sights of Cheshire, don't miss St Mary's of the Assumption Church. It's a winner among visitors and locals alike.