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Cherry Plain Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Cherry Plain.
Private Country home near Berkshires, vacation rental in Cherry Plain
Private Country home near Berkshires, vacation rental in Cherry Plain
Private Country home near Berkshires, vacation rental in Cherry Plain

Private Country home near Berkshires

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The following properties within 20 miles of Cherry Plain match all your filters:
Beautifully Renovated Condo, vacation rental in Cherry Plain
Beautifully Renovated Condo, vacation rental in Cherry Plain
Beautifully Renovated Condo, vacation rental in Cherry Plain

Beautifully Renovated Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Recently Updated Condo at Jiminy Peak, vacation rental in Cherry Plain
Recently Updated Condo at Jiminy Peak, vacation rental in Cherry Plain
Recently Updated Condo at Jiminy Peak, vacation rental in Cherry Plain

Recently Updated Condo at Jiminy Peak

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Private country home minutes from the Berkshires, vacation rental in Cherry Plain
Private country home minutes from the Berkshires, vacation rental in Cherry Plain
Private country home minutes from the Berkshires, vacation rental in Cherry Plain

Private country home minutes from the Berkshires

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Enchanting Modern Farmhouse with Picturesque Views, vacation rental in Cherry Plain
Enchanting Modern Farmhouse with Picturesque Views, vacation rental in Cherry Plain
Enchanting Modern Farmhouse with Picturesque Views, vacation rental in Cherry Plain

Enchanting Modern Farmhouse with Picturesque Views

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Mountainside Wyndham Bentley Brook! 2 Bd. dlx., vacation rental in Cherry Plain
Mountainside Wyndham Bentley Brook! 2 Bd. dlx., vacation rental in Cherry Plain
Mountainside Wyndham Bentley Brook! 2 Bd. dlx., vacation rental in Cherry Plain

Mountainside Wyndham Bentley Brook! 2 Bd. dlx.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Stephentown Hotel!, vacation rental in Cherry Plain
The Stephentown Hotel!, vacation rental in Cherry Plain
The Stephentown Hotel!, vacation rental in Cherry Plain

The Stephentown Hotel!

Private Room
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Wyndham Bentley Brook! 2 Bd. dlx. in Hancock, vacation rental in Cherry Plain
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock, vacation rental in Cherry Plain
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock, vacation rental in Cherry Plain

Wyndham Bentley Brook! 2 Bd. dlx. in Hancock

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Cherry Plain
Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Cherry Plain
Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Cherry Plain

Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe, vacation rental in Cherry Plain
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe, vacation rental in Cherry Plain
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe, vacation rental in Cherry Plain

Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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2 Bed Berkshire Getaway minutes to Jiminy Peak! Stephentown Hotel w/ Firepit BBQ, vacation rental in Cherry Plain
2 Bed Berkshire Getaway minutes to Jiminy Peak! Stephentown Hotel w/ Firepit BBQ, vacation rental in Cherry Plain
2 Bed Berkshire Getaway minutes to Jiminy Peak! Stephentown Hotel w/ Firepit BBQ, vacation rental in Cherry Plain

2 Bed Berkshire Getaway minutes to Jiminy Peak! Stephentown Hotel w/ Firepit BBQ

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Cherry Plain
Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Cherry Plain
Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Cherry Plain

Vacation Village in the Berkshires - 1 Bedroom

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Cherry Plain
Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Cherry Plain
Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Cherry Plain

Vacation Village in the Berkshires - 1 Bedroom

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cherry Plain
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cherry Plain
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cherry Plain

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Vacation Village In The Berkshires 5 Star Resort - Suite B, vacation rental in Cherry Plain
Vacation Village In The Berkshires 5 Star Resort - Suite B, vacation rental in Cherry Plain
Vacation Village In The Berkshires 5 Star Resort - Suite B, vacation rental in Cherry Plain

Vacation Village In The Berkshires 5 Star Resort - Suite B

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!, vacation rental in Cherry Plain
1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!, vacation rental in Cherry Plain
1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!, vacation rental in Cherry Plain

1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Vacation Village in the Berkshires 5 Star Resort  -  Suite A, vacation rental in Cherry Plain
Vacation Village in the Berkshires 5 Star Resort  -  Suite A, vacation rental in Cherry Plain
Vacation Village in the Berkshires 5 Star Resort  -  Suite A, vacation rental in Cherry Plain

Vacation Village in the Berkshires 5 Star Resort - Suite A

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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ONTARA...., vacation rental in Cherry Plain
ONTARA...., vacation rental in Cherry Plain
ONTARA...., vacation rental in Cherry Plain

ONTARA....

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Ski resort, vacation rental in Cherry Plain
Ski resort, vacation rental in Cherry Plain
Ski resort, vacation rental in Cherry Plain

Ski resort

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Cozy couple resort style condo overlooks the beautiful Massachusetts mountains., vacation rental in Cherry Plain
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains., vacation rental in Cherry Plain
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains., vacation rental in Cherry Plain

Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Wyndham Bentley Brook ~ Winter Recess, vacation rental in Cherry Plain
Wyndham Bentley Brook ~ Winter Recess, vacation rental in Cherry Plain
Wyndham Bentley Brook ~ Winter Recess, vacation rental in Cherry Plain

Wyndham Bentley Brook ~ Winter Recess

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Jiminy Peak ski in/ski out Wyndham Bentley Brook, vacation rental in Cherry Plain
Jiminy Peak ski in/ski out Wyndham Bentley Brook, vacation rental in Cherry Plain
Jiminy Peak ski in/ski out Wyndham Bentley Brook, vacation rental in Cherry Plain

Jiminy Peak ski in/ski out Wyndham Bentley Brook

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in Cherry Plain
Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in Cherry Plain
Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in Cherry Plain

Wyndham Bentley Brook Jiminy Peak ski in/out unit

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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2 Bedroom Deluxe Condo, Sleeps 8, Jiminy Peak Mountain Skiing, at Bentley Brook!, vacation rental in Cherry Plain
2 Bedroom Deluxe Condo, Sleeps 8, Jiminy Peak Mountain Skiing, at Bentley Brook!, vacation rental in Cherry Plain
2 Bedroom Deluxe Condo, Sleeps 8, Jiminy Peak Mountain Skiing, at Bentley Brook!, vacation rental in Cherry Plain

2 Bedroom Deluxe Condo, Sleeps 8, Jiminy Peak Mountain Skiing, at Bentley Brook!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Whitman Woods - A Berkshire Vacation, vacation rental in Cherry Plain
Whitman Woods - A Berkshire Vacation, vacation rental in Cherry Plain
Whitman Woods - A Berkshire Vacation, vacation rental in Cherry Plain

Whitman Woods - A Berkshire Vacation

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook - Jiminy Peak ski in/out, vacation rental in Cherry Plain
Wyndham Bentley Brook - Jiminy Peak ski in/out, vacation rental in Cherry Plain
Wyndham Bentley Brook - Jiminy Peak ski in/out, vacation rental in Cherry Plain

Wyndham Bentley Brook - Jiminy Peak ski in/out

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!, vacation rental in Cherry Plain
2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!, vacation rental in Cherry Plain
2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!, vacation rental in Cherry Plain

2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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2 Bed Berkshire Getaway * Stephentown Hotel! Minutes to Jiminy Peak! 2nd FL Apt., vacation rental in Cherry Plain
2 Bed Berkshire Getaway * Stephentown Hotel! Minutes to Jiminy Peak! 2nd FL Apt., vacation rental in Cherry Plain
2 Bed Berkshire Getaway * Stephentown Hotel! Minutes to Jiminy Peak! 2nd FL Apt., vacation rental in Cherry Plain

2 Bed Berkshire Getaway * Stephentown Hotel! Minutes to Jiminy Peak! 2nd FL Apt.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Bentley Brook Jiminy Peak ski in ski out, vacation rental in Cherry Plain
Bentley Brook Jiminy Peak ski in ski out, vacation rental in Cherry Plain
Bentley Brook Jiminy Peak ski in ski out, vacation rental in Cherry Plain

Bentley Brook Jiminy Peak ski in ski out

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook at Jiminy Peak ski in ski out, vacation rental in Cherry Plain
Wyndham Bentley Brook at Jiminy Peak ski in ski out, vacation rental in Cherry Plain
Wyndham Bentley Brook at Jiminy Peak ski in ski out, vacation rental in Cherry Plain

Wyndham Bentley Brook at Jiminy Peak ski in ski out

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook Condo Resort, vacation rental in Cherry Plain
Wyndham Bentley Brook Condo Resort, vacation rental in Cherry Plain
Wyndham Bentley Brook Condo Resort, vacation rental in Cherry Plain

Wyndham Bentley Brook Condo Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Bentley Brook Mountain Club at Jiminy Peak, vacation rental in Cherry Plain
Bentley Brook Mountain Club at Jiminy Peak, vacation rental in Cherry Plain
Bentley Brook Mountain Club at Jiminy Peak, vacation rental in Cherry Plain

Bentley Brook Mountain Club at Jiminy Peak

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Farm House in Mt. Meadow, vacation rental in Cherry Plain
Farm House in Mt. Meadow, vacation rental in Cherry Plain
Farm House in Mt. Meadow, vacation rental in Cherry Plain

Farm House in Mt. Meadow

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cherry Plain
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cherry Plain
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cherry Plain

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Berkshire Cabin on 27acres near Jiminy Peak. Fall & Winter booking now!, vacation rental in Cherry Plain
Private Berkshire Cabin on 27acres near Jiminy Peak. Fall & Winter booking now!, vacation rental in Cherry Plain
Private Berkshire Cabin on 27acres near Jiminy Peak. Fall & Winter booking now!, vacation rental in Cherry Plain

Private Berkshire Cabin on 27acres near Jiminy Peak. Fall & Winter booking now!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Wyndham  Bentley Brook - Sleeps 8 - Ski In/Out - Pools & More, vacation rental in Cherry Plain
Wyndham  Bentley Brook - Sleeps 8 - Ski In/Out - Pools & More, vacation rental in Cherry Plain
Wyndham  Bentley Brook - Sleeps 8 - Ski In/Out - Pools & More, vacation rental in Cherry Plain

Wyndham Bentley Brook - Sleeps 8 - Ski In/Out - Pools & More

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Enchanting forest hide-away, vacation rental in Cherry Plain
Enchanting forest hide-away, vacation rental in Cherry Plain
Enchanting forest hide-away, vacation rental in Cherry Plain

Enchanting forest hide-away

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A MAGIC SPOT: Booking spring and summer. Weekly, monthly discounts available, vacation rental in Cherry Plain
A MAGIC SPOT: Booking spring and summer. Weekly, monthly discounts available, vacation rental in Cherry Plain
A MAGIC SPOT: Booking spring and summer. Weekly, monthly discounts available, vacation rental in Cherry Plain

A MAGIC SPOT: Booking spring and summer. Weekly, monthly discounts available

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort, vacation rental in Cherry Plain
Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort, vacation rental in Cherry Plain
Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort, vacation rental in Cherry Plain

Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy Cabin on Resort Property with endless fun in Berkshire, vacation rental in Cherry Plain
Cozy Cabin on Resort Property with endless fun in Berkshire, vacation rental in Cherry Plain
Cozy Cabin on Resort Property with endless fun in Berkshire, vacation rental in Cherry Plain

Cozy Cabin on Resort Property with endless fun in Berkshire

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Cherry Plain
Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Cherry Plain
Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Cherry Plain

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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UMIQUE Country Condo, 1BR 1 BA - NEW, vacation rental in Cherry Plain
UMIQUE Country Condo, 1BR 1 BA - NEW, vacation rental in Cherry Plain
UMIQUE Country Condo, 1BR 1 BA - NEW, vacation rental in Cherry Plain

UMIQUE Country Condo, 1BR 1 BA - NEW

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Spacious Berkshire Getaway at Jiminy Peak, vacation rental in Cherry Plain
Spacious Berkshire Getaway at Jiminy Peak, vacation rental in Cherry Plain
Spacious Berkshire Getaway at Jiminy Peak, vacation rental in Cherry Plain

Spacious Berkshire Getaway at Jiminy Peak

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Cherry Plain
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Cherry Plain
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Cherry Plain

Mountainside: Large 3-level Jiminy Peak Home

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Home in the Berkshires, vacation rental in Cherry Plain
Home in the Berkshires, vacation rental in Cherry Plain
Home in the Berkshires, vacation rental in Cherry Plain

Home in the Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort, vacation rental in Cherry Plain
Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort, vacation rental in Cherry Plain
Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort, vacation rental in Cherry Plain

Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Stephentown Hotel Triplex 5 bedroom. Minutes to Jiminy Peak. Plus firepit & bbq., vacation rental in Cherry Plain
Stephentown Hotel Triplex 5 bedroom. Minutes to Jiminy Peak. Plus firepit & bbq., vacation rental in Cherry Plain
Stephentown Hotel Triplex 5 bedroom. Minutes to Jiminy Peak. Plus firepit & bbq., vacation rental in Cherry Plain

Stephentown Hotel Triplex 5 bedroom. Minutes to Jiminy Peak. Plus firepit & bbq.

Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Golden Triangle in the Berkshires, vacation rental in Cherry Plain
Golden Triangle in the Berkshires, vacation rental in Cherry Plain
Golden Triangle in the Berkshires, vacation rental in Cherry Plain

Golden Triangle in the Berkshires

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Christmas in The Berkshires, vacation rental in Cherry Plain
Christmas in The Berkshires, vacation rental in Cherry Plain
Christmas in The Berkshires, vacation rental in Cherry Plain

Christmas in The Berkshires

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Thanksgiving week lux condo/4 Berkshires, vacation rental in Cherry Plain
Thanksgiving week lux condo/4 Berkshires, vacation rental in Cherry Plain
Thanksgiving week lux condo/4 Berkshires, vacation rental in Cherry Plain

Thanksgiving week lux condo/4 Berkshires

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Frequently Asked Questions about Cherry Plain