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Holiday Homes in Cheshire

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Featured Holiday Homes in Cheshire

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Stunning 3BR Riverfront Log Home with Soaring Glass Wall & Private Forest
Fireplace, books

Stunning 3BR Riverfront Log Home with Soaring Glass Wall & Private Forest

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Stunning 3BR Riverfront Log Home with Soaring Glass Wall & Private Forest
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (71)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town
Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown
Interior

Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

10.0 out of 10, Exceptional, (23)
"The property was beautiful! The kids enjoyed fishing in the pond with their grandpa. The hosts were nice enough to let us have a small impromptu family cookout and were very helpful when we accidentally locked ourselves out. It was a great stay!"
Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown
General Williams Estate House Lenox/Stockbridge
Exterior

General Williams Estate House Lenox/Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (110)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
General Williams Estate House Lenox/Stockbridge
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

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

10.0 out of 10, Exceptional, (25)
"We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior detail

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (93)
"This was our third time at this property. We still love it and look forward to returning again."
Hearts Desire is a furnished whole house in a small, colorful garden center.
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 AU$1,714
includes taxes & fees
8 Sept - 9 Sept
Hancock Village Inn at Jiminy Peak
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 AU$1,034
includes taxes & fees
14 Sept - 15 Sept
Spacious 5-bedroom house in charming Lee with WiFi
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 AU$731
includes taxes & fees
8 Sept - 9 Sept
Comfortable Berkshires retreat on mtn resort, SISO
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (219)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake
Contemporary Berkshire Home with Views of Taconic Golf Course
Smart TV, fireplace, DVD player, books

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (6)
Contemporary Berkshire Home with Views of Taconic Golf Course
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Interior

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

9.6 out of 10, Exceptional, (71)
"We love this comfortable cottage and quiet location, perfect for a relaxing vacation spent bird watching, biking the nearby rail trail, and hiking with our dog. This was our fourth time staying here-- impressed with the beautiful updates to the master bedroom, now a suite with its own bathroom! We'll be coming back again!"
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
StrautmanHaus - All-Season Chalet at Berkshire East
Fridge, microwave, oven, stovetop

StrautmanHaus - All-Season Chalet at Berkshire East

9.8 out of 10, Exceptional, (13)
"The house was definitely nice and we enjoyed our stay. I didn’t give it 5 stars because the two downstairs bedrooms had a strong musty smell."
StrautmanHaus - All-Season Chalet at Berkshire East
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (128)
"Great"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stockbridge Village Cottage With Mountain View’s and walk to town
Outdoor dining

Stockbridge Village Cottage With Mountain View’s and walk to town

9.8 out of 10, Exceptional, (63)
"Perfect long weekend with family at this lovely home!"
Stockbridge Village Cottage With Mountain View’s and walk to town
Secluded Family Home in Serene Stockbridge Woods
Dining

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq
Fridge, microwave, oven, stovetop

Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

10.0 out of 10, Exceptional, (5)
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq
Sophisticated Lenox Retreat by Evergreen Home
Exterior

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Very quaint location, clean property, and great place to stay"
Sophisticated Lenox Retreat by Evergreen Home
Charming 3-bedroom farmhouse in Lenox
Terrace/patio

Charming 3-bedroom farmhouse in Lenox

10.0 out of 10, Exceptional, (1)
"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."
Charming 3-bedroom farmhouse in Lenox
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

Find out more about Cheshire

Find out more about Cheshire

Cheshire Holiday Homes information

Number of reviews
Accommodation
311 Holiday Homes
Lowest Price
AU$731
Highest Price
AU$1,714

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