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Cheshire Vacation Rentals

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

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, vacation rental in Cheshire

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

8 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, vacation 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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Remote and Relaxing Cabin in the Berkshires, vacation rental in Cheshire

Remote and Relaxing Cabin in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Waterfront home with deep water dock on Onota Lake, vacation 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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Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak, vacation 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, vacation rental in Cheshire

Grand Colonial Home in the Heart of The Berkshires

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter, vacation rental in Cheshire

Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer, vacation rental in Cheshire

Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home in the Berkshires, vacation 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., vacation 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, vacation 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, vacation 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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Ashmere Lake Log Cabin with privacy / 2 Bedrooms, vacation rental in Cheshire

Ashmere Lake Log Cabin with privacy / 2 Bedrooms

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Retreat in the Woods, vacation rental in Cheshire

Retreat in the Woods

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BERKSHIRES-3BR2BA now-9/9  &/or  11/1-WINTER/SPRING RENT - NR JIMINY PK, vacation rental in Cheshire

BERKSHIRES-3BR2BA now-9/9 &/or 11/1-WINTER/SPRING RENT - NR JIMINY PK

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Gathering at High Mowing Williamstown, vacation rental in Cheshire

The Gathering at High Mowing Williamstown

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Berkshire house w/ fireplace, A/C, WiFi & laundry, vacation rental in Cheshire

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

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Exquisite Apartment in Grand Victorian Home 1, vacation 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, vacation 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, vacation 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!, vacation 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, vacation 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, vacation 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, vacation 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, vacation 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, vacation 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, vacation 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, vacation 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, vacation rental in Cheshire

Christmas in The Berkshires

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Thanksgiving week lux condo/4 Berkshires, vacation 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!, vacation 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, vacation 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, vacation rental in Cheshire

The Bear Den

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tentrr Signature Site - Hidden Hoosic   Riverside Camp, vacation 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, vacation rental in Cheshire

Tentrr Signature Site - Round Mountain Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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A roomy remodeled retreat close to MassMoCA, vacation rental in Cheshire

A roomy remodeled retreat close to MassMoCA

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, vacation rental in Cheshire

Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences

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

Apartment Newly Remodeled Super Location

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Brookman - Newly Renovated 6,000 SF Estate on 40 Acres, vacation 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, vacation rental in Cheshire

Tentrr Signature Site - Hancock Haven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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