Cheshire Holiday Homes
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Featured Holiday Homes in Cheshire
![Berkshiren kylävaunupaikka](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/82951d4a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Berkshiren kylävaunupaikka
Lanesborough, MA
The price is €223 per night
€223
includes taxes & fees
20 Feb - 21 Feb
During your stay at this holiday home, you'll be close to Crane Museum of Papermaking. Free WiFi and a kitchen are available in the holiday home.
Keittiö
Ilmainen Wi-Fi
![Rauha ja hiljainen järvellä](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/0443d9de_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Rauha ja hiljainen järvellä
Becket, MA
Our customers tell us they can't get enough of this holiday home's great location. During your stay, you'll be close to Pyramid Lake. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Keittiö
Pyykinpesukone
![Charlemont Retreat on Chickley River w/ EV Charger](https://images.trvl-media.com/lodging/75000000/74880000/74874500/74874437/93377978_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Charlemont Retreat on Chickley River w/ EV Charger
Hawley, Massachusetts
During your stay at this holiday home, you'll be within walking distance of Mohawk Trail State Forest. Enjoy features like free WiFi in public areas and self-parking (surcharge). The holiday home offers a kitchen and a washer/dryer.
![Amore Estate - beautiful room with many places to explore and relax in.](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/b09713b5_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
During your stay at this holiday home, you'll be within walking distance of Wyndhurst Golf & Club. An outdoor pool is available. The holiday home offers a private pool and in-room jetted baths.
Uima-allas
Keittiö
![Comfortable Berkshires retreat on mtn resort, SISO](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/642a7587_edited_52c6_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Comfortable Berkshires retreat on mtn resort, SISO
Hancock, MA
The price is €662 per night
€662
includes taxes & fees
23 Feb - 24 Feb
During your stay at this holiday home, you'll be within walking distance of Jiminy Peak Mountain Resort. Enjoy features like a gym, 1 hot tub and an arcade/games room. The holiday home includes amenities such as free WiFi and a kitchen.
Uima-allas
Poreallas
![Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/d60a3def_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock, MA
The price is €590 per night
€590
includes taxes & fees
23 Feb - 24 Feb
During your stay at this holiday home, you're just a quick walk from Jiminy Peak Mountain Resort. Enjoy features like a gym and 1 hot tub. The holiday home includes amenities such as a kitchen and 3 bathrooms.
![Country Living just minutes from Everything!](https://images.trvl-media.com/lodging/70000000/69650000/69640700/69640625/468a4dfd_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Country Living just minutes from Everything!
Pittsfield, MA
During your stay at this holiday home, you're just a quick walk from Tracy Brook Wildlife Sanctuary. A gym is available. Free WiFi and a kitchen are available in the holiday home.
![Hearts Desire is a furnished whole house in a small, colorful garden center.](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/128e06d4_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hearts Desire is a furnished whole house in a small, colorful garden center.
Lanesborough, MA
During your stay at this holiday home, you'll be close to Jiminy Peak Mountain Resort. You'll find features such as 1 hot tub. Free WiFi and a kitchen are available in the holiday home.
![14mi to Mt. Snow! Arcade, Private Suite, King Bed!](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/a009c5fa_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Whitingham, VT
The price is €498 per night
€498
includes taxes & fees
11 Mar - 12 Mar
During your stay at this holiday home, you'll be close to Jacksonville Pond. Enjoy features like a gym and an arcade/games room. The holiday home includes amenities such as free WiFi and in-room jetted baths.
Keittiö
Pyykinpesukone
![Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.](https://images.trvl-media.com/lodging/97000000/96240000/96232500/96232485/88a517ee_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
During your stay at this holiday home, you'll be close to Bas Ridge Golf Course. In-room jetted baths and a patio are available in the holiday home.
![Pristine Home In Becket Woods](https://images.trvl-media.com/lodging/84000000/83270000/83269800/83269705/79263c62_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Pristine Home In Becket Woods
Becket, Massachusetts
During your stay at this holiday home, you'll be close to Becket Land Trust Historic Quarry. The holiday home includes amenities such as a kitchen and 2 bathrooms.
Keittiö
Lemmikkiystävällinen
![Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/775a6169_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington, VT
The price is €308 per night
€308
includes taxes & fees
18 Feb - 19 Feb
During your stay at this holiday home, you're just a quick walk from Green Mountain National Forest. The holiday home includes amenities such as a kitchen and a balcony.
Keittiö
Pyykinpesukone
![Hancock Village Inn at Jiminy Peak](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hancock Village Inn at Jiminy Peak
Hancock, MA
The price is €1,072 per night
€1,072
includes taxes & fees
25 Feb - 26 Feb
During your stay at this holiday home, you're just a quick walk from Pittsfield State Forest. Features include 1 hot tub, an arcade/games room and a library. Enjoy your stay with amenities like a kitchen and a washer/dryer in the holiday home.
Poreallas
Keittiö
![Quintessential 6-BR Berkshires Lodge](https://images.trvl-media.com/lodging/90000000/89790000/89786400/89786307/190f5311_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Quintessential 6-BR Berkshires Lodge
Becket, MA
During your stay at this holiday home, you're just a quick walk from October Mountain State Forest. 1 hot tub is available. Enjoy your stay with amenities like a private pool and a kitchen in the holiday home.
Uima-allas
Poreallas
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.
Cheshire Holiday Homes essential information
Accommodation | 228 Holiday Homes |
---|---|
Lowest Price | €223 |
Highest Price | €1,072 |
Popular accommodation | Berkshiren kylävaunupaikka , Rauha ja hiljainen järvellä, Charlemont Retreat on Chickley River w/ EV Charger, Amore Estate - beautiful room with many places to explore and relax in., Comfortable Berkshires retreat on mtn resort, SISO, Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, Country Living just minutes from Everything! , Hearts Desire is a furnished whole house in a small, colorful garden center., 14mi to Mt. Snow! Arcade, Private Suite, King Bed!, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. , Pristine Home In Becket Woods, Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat, Hancock Village Inn at Jiminy Peak, Quintessential 6-BR Berkshires Lodge, Chic Pittsfield Home With A View! |
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