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Cheshire, MA Holiday Rentals, Apartments and Villas
Holiday Rentals
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Massachusetts (MA)
Berkshires
Cheshire, MA Holiday Rentals, Apartments and Villas
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Kid friendly (48)
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Distance from
5 km
Whitney's Farm Market & Garden Center
St Mary's of the Assumption Church
Cheshire Glassworks
Elmartin Farm
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49 rentals
in Cheshire.
19th c. Barn in the Berkshires
84
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 9
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Sleeps
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As seen on
Berkshires Lakefront Retreat by Evergreen Home
6
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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The following properties within 32 kms of Cheshire match all your filters:
Berkshire Village Carriage House - Super Private!!
200
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Sleeps
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Hearts Desire is a furnished whole house in a small, colorful garden center.
34
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Sleeps
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Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside
16
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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Sleeps
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Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
31
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
12
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 10
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A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
111
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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Sleeps
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Charming historic cottage on scenic road to Mt. Greylock
21
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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Sleeps
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Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.
10
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 6
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Sleeps
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Studio Suite, w/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Monthly/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Park Street Penthouse Apartment
2
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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Available for Winter Rental, Healthcare, Central
10
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Sleeps
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Historic Stone Church in The Berkshires
3
Holiday Rental House
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1 bedroom
2 bathrooms
Sleeps 2
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Sleeps
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As seen on
Wyndham Bentley Brook Condo Resort
5
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 8
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Sleeps
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
1
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 8
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Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
3
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 8
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As seen on
Lakeside Berkshires Home Near Hiking & Skiing!
4
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 7
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Sleeps
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As seen on
Wildlife Lakeside Cottage
1
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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As seen on
Chic Berkshire Retreat by Evergreen Home
6
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Huge Beautiful House-fits 2 families-16 Acres -Low rates- 2 min from Jiminy Peak
53
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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As seen on
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
1
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
1
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 7
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As seen on
Berkshire Winter Fun! Family-friendly escape near skiing, hikes, museums, & more
18
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Sleeps
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Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
10
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 12
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As seen on
Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA
3
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Family Friendly Townhouse in the Heart of Jiminy Peak
11
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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Sleeps
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Brooksong, the perfect Berkshires getaway
10
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Sleeps
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6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
11
Holiday Rental House
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6 bedrooms
5 bathrooms
Sleeps 14
Match:
Sleeps
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Entire home in Dalton, Massachusetts, United States
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Sleeps
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Mountain Blossom Retreat by Evergreen Home
3
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Sleeps
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3 Bedroom home w/ lake and mountain views near skiing, and cultural
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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As seen on
Lake Views & Dock Access - Pittsfield Cottage!
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Entire cottage in Berkshire Villiage
3
Holiday Rental House
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1 bedroom
2 bathrooms
Sleeps 4
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Sleeps
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New!! Breathtaking Post & Beam home minutes from skiing, music, arts and hiking
3
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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Lakefront Home on Pontoosuc Lake, the Berkshires
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Ray of Sunshine Berkshire Home on Pontoosuc Lake
1
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 14
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Sleeps
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Comfortable Berkshires retreat on mtn resort, SISO
Holiday Rental House
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12 bedrooms
3 bathrooms
Sleeps 12
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Sleeps
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Golf House by Mt Greylock - Walkable Adventures!
3
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 7
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Sleeps
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Deluxe One Bedroom and One Bathroom with Full Amenities
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 5
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Sleeps
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Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
2
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Holiday Rental House
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1 bedroom
2 bathrooms
Sleeps 8
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Sleeps
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Cozy Cottage in Berkshires: Minutes to Jiminy Peak
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
1
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
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Sleeps
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6-BR Expansive Berkshires Estate w Pool
2
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 14
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1
Showing results 1-49 of 49
Frequently Asked Questions about Cheshire
Do any holiday rentals in Cheshire have a pool?
Yes, here are some popular holiday rentals in Cheshire that have a pool:
19th c. Barn in the Berkshires
Berkshires Lakefront Retreat by Evergreen Home
Berkshire Village Carriage House - Super Private!!
See all holiday rentals with a pool in Cheshire on Tripadvisor
Do any holiday rentals in Cheshire have internet access?
Yes, here are some popular holiday rentals in Cheshire that have internet access:
19th c. Barn in the Berkshires
Berkshires Lakefront Retreat by Evergreen Home
Berkshire Village Carriage House - Super Private!!
See all holiday rentals in Cheshire on Tripadvisor
What are the best pet friendly rentals in Cheshire?
The best pet friendly rentals in Cheshire are:
19th c. Barn in the Berkshires
Berkshires Lakefront Retreat by Evergreen Home
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside
See all pet friendly holiday rentals in Cheshire on Tripadvisor
What are some great rentals in Cheshire that are kid friendly?
Some of the most popular kid friendly rentals in Cheshire are:
19th c. Barn in the Berkshires
Berkshires Lakefront Retreat by Evergreen Home
Berkshire Village Carriage House - Super Private!!
See all kid friendly holiday rentals in Cheshire on Tripadvisor
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