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Cheshire Holiday Rentals

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50 rentals in Cheshire.
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19th c. Renovated Barn in the Berkshires, holiday rental in Cheshire

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Huge Luxe Williamstown Updated Victorian,  All Ensuite Baths, Walk to Spring St!, holiday rental in Cheshire

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

5 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Berkshire Village Carriage House, holiday rental in Cheshire

Berkshire Village Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, holiday rental in Cheshire

New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, holiday rental in Cheshire

Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, holiday rental in Cheshire

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, holiday rental in Cheshire

A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy renovated cabin in Williamstown, steps from hiking trails, holiday rental in Cheshire

Cozy renovated cabin in Williamstown, steps from hiking trails

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tranquil Lake House Getaway on Onota Lake, holiday rental in Cheshire

Tranquil Lake House Getaway on Onota Lake

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Berkshire Lake House Vacation Rental, holiday rental in Cheshire

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, holiday rental in Cheshire

Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Waterfront home with deep water dock on Onota Lake, holiday rental in Cheshire

Beautiful Waterfront home with deep water dock on Onota Lake

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Remote and Relaxing Cabin in the Berkshires, holiday rental in Cheshire

Remote and Relaxing Cabin in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A roomy remodeled retreat close to MassMoCA, holiday rental in Cheshire

A roomy remodeled retreat close to MassMoCA

4 bedrooms
2 bathrooms
Sleeps 8
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Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak, holiday rental in Cheshire

Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Grand Colonial Home in the Heart of The Berkshires, holiday rental in Cheshire

Grand Colonial Home in the Heart of The Berkshires

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Home in the Berkshires, holiday rental in Cheshire

Home in the Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., holiday rental in Cheshire

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy and quaint country cottage, walk to downtown Williamstown, holiday rental in Cheshire

Cozy and quaint country cottage, walk to downtown Williamstown

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, holiday rental in Cheshire

6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Retreat in the Woods, holiday rental in Cheshire

Retreat in the Woods

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Berkshire Getaway with Scenic Lake Views & Access, holiday rental in Cheshire

Charming Berkshire Getaway with Scenic Lake Views & Access

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Cheshire

Berkshire house w/ fireplace, A/C, WiFi & laundry

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Gathering at High Mowing Williamstown, holiday rental in Cheshire

The Gathering at High Mowing Williamstown

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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A MAGIC SPOT: Booking Fall and the Ski Season now!, holiday rental in Cheshire

A MAGIC SPOT: Booking Fall and the Ski Season now!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Exquisite Apartment in Grand Victorian Home 1, holiday rental in Cheshire

Exquisite Apartment in Grand Victorian Home 1

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun, holiday rental in Cheshire

Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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6BR Berkshire Bliss - 38 private acres - close to skiing and town, holiday rental in Cheshire

6BR Berkshire Bliss - 38 private acres - close to skiing and town

6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Mounatin Getaway in the Heart of the Berkshires!, holiday rental in Cheshire

Mounatin Getaway in the Heart of the Berkshires!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, holiday rental in Cheshire

Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Whitman Woods - A Berkshire Vacation, holiday rental in Cheshire

Whitman Woods - A Berkshire Vacation

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Golden Triangle in the Berkshires, holiday rental in Cheshire

Golden Triangle in the Berkshires

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bentley/Wyndham Hancock Mass at Jiminy Peak, holiday rental in Cheshire

Bentley/Wyndham Hancock Mass at Jiminy Peak

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite Apartment in Grand Victorian 2, holiday rental in Cheshire

Exquisite Apartment in Grand Victorian 2

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Meadow House 4 bdrm 4 bath house, holiday rental in Cheshire

The Meadow House 4 bdrm 4 bath house

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, holiday rental in Cheshire

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Christmas in The Berkshires, holiday rental in Cheshire

Christmas in The Berkshires

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Thanksgiving week lux condo/4 Berkshires, holiday rental in Cheshire

Thanksgiving week lux condo/4 Berkshires

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, holiday rental in Cheshire

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, holiday rental in Cheshire

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Bear Den, holiday rental in Cheshire

The Bear Den

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Picturesque Cottage with Sunroom on Ashmere Lake!, holiday rental in Cheshire

Picturesque Cottage with Sunroom on Ashmere Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Hidden Hoosic   Riverside Camp, holiday rental in Cheshire

Tentrr Signature Site - Hidden Hoosic Riverside Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Round Mountain Camp, holiday rental in Cheshire

Tentrr Signature Site - Round Mountain Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, holiday rental in Cheshire

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Apartment Newly Remodeled Super Location, holiday rental in Cheshire

Apartment Newly Remodeled Super Location

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Lakeside Berkshires Home Near Hiking & Skiing, holiday rental in Cheshire

NEW! Lakeside Berkshires Home Near Hiking & Skiing

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Peaceful Family Home w/ Fire Pit & Large Yard, holiday rental in Cheshire

NEW! Peaceful Family Home w/ Fire Pit & Large Yard

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Brookman - Newly Renovated 6,000 SF Estate on 40 Acres, holiday rental in Cheshire

The Brookman - Newly Renovated 6,000 SF Estate on 40 Acres

8 bedrooms
6 bathrooms
Sleeps 25
Match: Sleeps
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Tentrr Signature Site - Hancock Haven, holiday rental in Cheshire

Tentrr Signature Site - Hancock Haven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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