Catamount Ski Area pickleball Stays, Resort Rentals, & Homes

     

1 Court Nearby

House

Superb Views - Sunsets, Mountains, Valley

• Hillsdale
• ·
• Town of Copake
• 2.52 mi to center

10.0

Exceptional

(17 Reviews)

4 Bedrooms 3 Baths 8 Guests 2500 ft²

• 
  Private Pool
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $467/Night 7 Nights - US $3,266

View Deal

     

Hotel

Holiday House Motel

• New York
• ·
• Hillsdale
• 2.57 mi to center

6.8

Good

(55 Reviews)

1 Bath 260.49 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Air Conditioner
• 
  Internet

US $115/Night 7 Nights - US $805

View Deal

      Price Dropped

Hotel

Prospect Berkshires

• Great Barrington
• ·
• North Egremont
• 0.35 mi to center

10.0

Exceptional

(45 Reviews)

1 Bath

• 
  Parking
• 
  Pool
• 
  Spa
• 
  Balcony/Terrace

US $419/Night 7 Nights - US $2,932

View Deal

     

1 Court Nearby

House

Best Berkshire “Readaway” Stay! New reno, stunning private acreage, cultural gem

• Great Barrington
• ·
• Egremont
• 1.43 mi to center

10.0

Exceptional

(2 Reviews)

3 Bedrooms 2 Baths 8 Guests 1900 ft²

• 
  Hot Tub
• 
  Parking
• 
  Skiing
• 
  Ocean View

US $936/Night 7 Nights - US $6,550

View Deal

     

House

Catamount, Zip Line, Private Setting, Book Now!

• Great Barrington
• ·
• Egremont
• 1.60 mi to center

4 Bedrooms 2 Baths 8 Guests 2303.48 ft²

• 
  Parking
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $465/Night 7 Nights - US $3,257

View Deal

      Highly Rated

Hotel

Little Cat Lodge

• New York
• ·
• Hillsdale
• 4.20 mi to center

9.6

Exceptional

(146 Reviews)

1 Bath

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  Spa

US $218/Night 7 Nights - US $1,528

View Deal

     

1 Court Nearby

House

Nature Retreat Near Prospect Lake

• Great Barrington
• ·
• North Egremont
• 0.38 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 10 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $456/Night 7 Nights - US $3,191

View Deal

     

Hotel

Prospect Berkshires

• Great Barrington
• ·
• North Egremont
• 0.37 mi to center

9.6

Exceptional

(32 Reviews)

7 Baths 361.36 ft²

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  Skiing

US $478/Night 7 Nights - US $3,348

View Deal

     

Hotel

The Brooks Motel

• New York
• ·
• Hillsdale
• 2.57 mi to center

7.4

Very Good

(156 Reviews)

1 Bath

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $160/Night 7 Nights - US $1,121

View Deal

      Highly Rated

Ski Chalet

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

• New York
• ·
• Hillsdale
• 2.42 mi to center

10.0

Exceptional

(109 Reviews)

2 Bedrooms 1 Bath 6 Guests 1200 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $256/Night 7 Nights - US $1,793

View Deal

     

Hotel

The Cozy Cat Motel at Catamount

• Hillsdale
• ·
• Town of Copake
• 4.83 mi to center

9.0

Exceptional

(2 Reviews)

8 Baths 1582.29 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  View
• 
  Air Conditioner

US $283/Night 7 Nights - US $1,982

View Deal

     

House

Little Gem On Baldwin Hill In South Egremont

• Great Barrington
• ·
• Egremont
• 1.11 mi to center

10.0

Exceptional

(21 Reviews)

2 Bedrooms 2 Baths 4 Guests 920 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $564/Night 7 Nights - US $3,947

View Deal

     

Hotel

The Brooks Motel

• New York
• ·
• Hillsdale
• 2.56 mi to center

7.2

Very Good

(81 Reviews)

5 Baths 139.93 ft²

• 
  Parking
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $192/Night 7 Nights - US $1,347

View Deal

     

Apartment

Comfortable, renovated 2 bedroom apartment in historic grist mill.

• Great Barrington
• ·
• Egremont
• 1.27 mi to center

10.0

Exceptional

(7 Reviews)

2 Bedrooms 2 Baths 4 Guests

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $319/Night 7 Nights - US $2,232

View Deal

     

House

Restored Historic 1850s Barn "Carriage House" Studio @ Hillsdale Town Center

• New York
• ·
• Hillsdale
• 2.19 mi to center

6.8

Good

(3 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $228/Night 7 Nights - US $1,593

View Deal

     

House

The Brooks Buy Out, Wedding Groups Inquire Today!

• New York
• ·
• Hillsdale
• 2.56 mi to center

1 Bedroom 1 Bath 56 Guests

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $3,263/Night 7 Nights - US $22,838

View Deal

     

Other

Private Unit in shared 1830 Farmhouse

• New York
• ·
• Hillsdale
• 2.26 mi to center

10.0

Exceptional

(3 Reviews)

2 Bedrooms 1 Bath 4 Guests

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $402/Night 7 Nights - US $2,811

View Deal

      Highly Rated

Ski Chalet

Beautifully decorated & immaculate log chalet on 3 acres, winter views.

• New York
• ·
• Hillsdale
• 2.96 mi to center

10.0

Exceptional

(170 Reviews)

3 Bedrooms 2 Baths 6 Guests 1200 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $288/Night 7 Nights - US $2,015

View Deal

     

House

Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires

• Hillsdale
• ·
• Town of Copake
• 2.64 mi to center

10.0

Exceptional

(48 Reviews)

6 Bedrooms 5 Baths 10 Guests 3000 ft²

• 
  Private Pool
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $1,616/Night 7 Nights - US $11,315

View Deal

      Price Dropped

House

Log style home 4 miles to Catamount with fitness room

• Great Barrington
• ·
• Egremont
• 1.24 mi to center

10.0

Exceptional

(17 Reviews)

4 Bedrooms 3 Baths 7 Guests 2400 ft²

• 
  Hot Tub
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

US $475/Night 7 Nights - US $3,325

View Deal

     

House

Timberdoodle-a mountainside retreat

• Great Barrington
• ·
• Egremont
• 2.06 mi to center

10.0

Exceptional

(13 Reviews)

3 Bedrooms 2 Baths 6 Guests 1600 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  View
• 
  Kitchen

US $429/Night 7 Nights - US $3,005

View Deal

     

House

Stunning views & charming spacious 4-BR home pool and fireplace in Copake Falls

• Hillsdale
• ·
• Town of Copake
• 2.36 mi to center

10.0

Exceptional

(11 Reviews)

4 Bedrooms 3 Baths 10 Guests

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $832/Night 7 Nights - US $5,821

View Deal

      Price Dropped

House

Catamount, Zip Line, Private Setting, Book Now!

• Great Barrington
• ·
• Egremont
• 1.60 mi to center

10.0

Exceptional

(10 Reviews)

4 Bedrooms 2 Baths 8 Guests 2300 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $555/Night 7 Nights - US $3,882

View Deal

     

House

Historic 1850s Berkshires Retreat "Bell House" w/Private Pool @ Town Center

• New York
• ·
• Hillsdale
• 2.35 mi to center

10.0

Exceptional

(7 Reviews)

5 Bedrooms 4 Baths 10 Guests 2900 ft²

• 
  Private Pool
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $532/Night 7 Nights - US $3,724

View Deal