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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In one month
26 Sep - 28 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Vacation Homes in Cheshire

Our top choices for Cheshire vacation homes

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is SAR 608
SAR 1,471 total
includes taxes & fees
3 Sep - 4 Sep
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Fridge, microwave, oven, stovetop

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

10.0 out of 10, Exceptional, (12)
"Great property, plenty of space and room for all. Location is ideal"
The price is SAR 840
SAR 2,021 total
includes taxes & fees
3 Sep - 4 Sep
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is SAR 1,300
SAR 2,381 total
includes taxes & fees
10 Sep - 11 Sep
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is SAR 563
SAR 855 total
includes taxes & fees
16 Sep - 17 Sep
Berkshire Village Carriage House - Super Private!!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is SAR 856
SAR 1,915 total
includes taxes & fees
1 Sep - 2 Sep
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is SAR 1,407
SAR 1,899 total
includes taxes & fees
1 Sep - 2 Sep
Bungalow in the Berkshires
Two Brooks Lodge
Panoramic House | Private kitchen

Two Brooks Lodge

3.0 star property
4.8 out of 10, (3)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...
Two Brooks Lodge
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (21)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is SAR 760
SAR 1,658 total
includes taxes & fees
4 Sep - 5 Sep
North Getaway Cottage
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is SAR 604
SAR 1,798 total
includes taxes & fees
1 Sep - 2 Sep
Comfortable Berkshires retreat on mtn resort, SISO
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is SAR 765
SAR 1,776 total
includes taxes & fees
1 Sep - 2 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is SAR 2,060
SAR 3,930 total
includes taxes & fees
2 Sep - 3 Sep
Hancock Village Inn at Jiminy Peak
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is SAR 778
SAR 1,142 total
includes taxes & fees
1 Sep - 2 Sep
Experience Timeless Elegance in The Edith Wharton Room!
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is SAR 1,782
SAR 3,231 total
includes taxes & fees
5 Sep - 6 Sep
Spacious 5-bedroom house in charming Lee with WiFi
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is SAR 788
SAR 1,731 total
includes taxes & fees
3 Sep - 4 Sep
Near Tanglewood: Historic Summer Retreat
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (71)
"We had a wonderful stay, thank you! "
The price is SAR 983
SAR 2,029 total
includes taxes & fees
1 Sep - 2 Sep
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is SAR 898
SAR 1,293 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is SAR 958
SAR 1,372 total
includes taxes & fees
1 Sep - 2 Sep
Historic Susan B. Anthony Room - Cozy & Charming Stay
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