Holiday Homes in Cheshire

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 July - 5 July
In three months
31 July - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Cheshire holiday homes

Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$515
includes taxes & fees
11 May - 12 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
TV

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AU$504
includes taxes & fees
10 May - 11 May
Florida Mountain Log Cabin
Smart TV

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AU$283
includes taxes & fees
10 May - 11 May
Cozy Home in Pownal VT
Exterior

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is AU$737
includes taxes & fees
27 May - 28 May
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Exterior

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$607
includes taxes & fees
11 May - 12 May
North Getaway Cottage
Dining

Charlemont Chalet - A 15 Acre Private Retreat

Charlemont Chalet - A 15 Acre Private Retreat
Charlemont
The price is AU$947
includes taxes & fees
13 May - 14 May
Charlemont Chalet - A 15 Acre Private Retreat
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AU$851
includes taxes & fees
12 May - 13 May
5BR Berkshire Home Mins To The Mountain
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AU$299
includes taxes & fees
27 May - 28 May
Private bed with En-suite bathroom Marigold Room
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is AU$985
includes taxes & fees
11 May - 12 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (9 reviews)
"Kind and responsive host."
United States
Javier
The price is AU$744
includes taxes & fees
11 May - 12 May
Comfortable Berkshires retreat on mtn resort, SISO
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (6 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is AU$508
includes taxes & fees
17 May - 18 May
The Greylock Cabin
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AU$670
includes taxes & fees
13 May - 14 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
TV

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AU$686
includes taxes & fees
13 May - 14 May
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$773
includes taxes & fees
13 May - 14 May
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is AU$538
includes taxes & fees
10 May - 11 May
Two Brooks Lodge
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (3 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AU$643
includes taxes & fees
22 May - 23 May
Riverbend Berkshire East Basecamp - 3 bedrooms available
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is AU$1,155
includes taxes & fees
20 May - 21 May
Spacious 5-bedroom house in charming Lee with WiFi
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,538
includes taxes & fees
20 May - 21 May
Hancock Village Inn Near Jiminy Peak
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.
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Top Cheshire Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Everything was great"
Riri 2-night trip
Posted 9 hours ago
The Red Lion Inn

Find out more about Cheshire

Cheshire Holiday Homes information

Number of reviews
123
Accommodation
282 Holiday Homes
Lowest Price
AU$283
Highest Price
AU$1,538