Cherry Plain Rentals

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88 Houses

Tentrr - Center Berlin Campsite

Cherry Plain tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$133

Great rentals within 20 miles that match your search

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$196

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 19 minutes

Price per night from

$288

Stunning New Construction All SeasonLakefront Home

Valatie house

3 bedrooms / 3 bathrooms / sleeps 5

“Amazing House!” The Doll house was such an exquisite stay! We had a couples retreat for Valentines day and the stay at this lake house was awesome from the moment we got here. The tub amazing, the kitchen amazing, and stay extraordinary! The lake was frozen but it was all worth it. I am already booking it for Spring 2013!! Thank you Mary (homeowner)!! She is great and helpful from the start!!!

Price per night from

$280

3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / sleeps 15

Price per night from

$213

To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

“Incredible vacation stay or seasonal rental” My family rented this home for an entire summer. The house is beautiful and perfectly suited for any sized family. We stayed with two adults and three children (infant-7yrs old), but also had several occasions with overnight guests. Three bedrooms are upstairs, leaving one/two rooms downstairs that functioned as a guest area. It was a perfect scenario with one of the two full bathrooms downstairs, our guests had full privacy. The house is very well kept, comfortable furniture, modern kitchen, and gorgeous views from the 50+ windows! The back yard is huge and our children spent many hours running around and playing freely. We were very pleased with the quietness and safety of the neighborhood. West Stockbridge is a prime and central location for all of the Berkshire's attractions. We have rented seasonal homes in the Berkshires for eleven years and this has been our best experience, by far. The homeowners are extremely welcoming and accommodating, making sure we were comfortable during our stay. We highly recommend this property!

Price per night from

$403

2200sf Country House on 16 Acres-2 Miles to Jiminy

Hancock house

4 bedrooms / 2 bathrooms / sleeps 9

“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slopes. well maintained and very clean.

Price per night from

$258

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$721

Vacation Village in the Berkshires Available July 22-29

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$180

Pocumtuck Cabin

North Adams log cabin

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$143

Beautiful Berkshire Country Estate

Old Chatham house

8 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$1,030

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 18 minutes

Price per night from

$229

Mohawk Cabin

North Adams log cabin

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$189

INTERIOR DESIGNERS BOTANICAL COTTAGE

Lenox cottage

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$206

Price per night from

$258

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

Richmond house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$572

Wampanoag Cabin

North Adams log cabin

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$143

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / sleeps 6

“Clean, Comfortable and Convenient” This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels take you to Northwest MA.

Price per night from

$166

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

“Handy, convenient, comfortable, well equipped and peaceful rental in terrific location.” In some rentals, you have to bring literally everything. This place was just the opposite. Great linens provided, napkins, paper towels and toilet paper and various necessities for cooking. Very roomy with 4 bedrooms and 5 beds, a good shower, hair dryer, washer dryer, good seating in the living room. Good lighting in the bedrooms, so appreciated. Convenient parking, walking distance to the town of Lenox with shops and restaurants at hand. Hope i have the chance to come back.

Price per night from

$229

NEW! Lakefront Averill Park Home w/Patio, Fire Pit

Averill Park cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 6 minutes

Price per night from

$126

Mahican Cabin

North Adams log cabin

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$189

Karin's Place

Bennington house

7 bedrooms / 6 bathrooms / sleeps 30

Price per night from

$1,545

Wyndham Bentley Brook at Jiminy Peak

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$286

NEW! Lenox Home Mins to Tanglewood Shakespeare &Co

Lenox house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 6 minutes

Price per night from

$241

Beautiful Vacation Home on a Private Lake

Petersburg house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$245

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$262

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / sleeps 6

“Weekend getaway” Lovely house. Nicely updated. Right next to the bike trail! Beautiful view of the lake. Great family fun. Thank you.

Responds fast! avg. 1 hour 41 minutes

Price per night from

$223

Berkshires Summer Rental Beaver Pond Hancock MA

Hancock condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$115

NEW! Family Home w/Game Room - 3 Mi to Jiminy Peak

Hancock house

4 bedrooms / 3 bathrooms / sleeps 20

Responds fast! avg. 1 hour 6 minutes

Price per night from

$286

Tentrr – Hidden Hoosic Riverside Camp

Clarksburg tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$199

Tentrr - Round Mountain Campsite

Hancock tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$139

Tentrr - Sweet Stream Sanctuary

West Lebanon tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$172

NEW! Charming Berkshires Cottage on Ashmere Lake

Hinsdale cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 25 minutes

Price per night from

$223

House On Main Street

Williamstown house

4 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 1 hour 19 minutes

Price per night from

$1,087

Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$121

The Lodge at Fox Hollow

Petersburg house

2 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$298

Tentrr - Berkshire Mountain Hideaway

Richmond tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$127

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$344

Viewing 38 of 88
rentals in Cherry Plain

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