Properties

All All listings (26)
  • Open and airy master bedroom with king bed and air conditioning.
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  • Relax by Cheshire Lake, just a short drive away. Great for kayaking, fishing, and lakeside picnics.
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Ridgeview Retreat | Valley Views • Sleeps 6

  • 6 guests
  • 3 bedrooms
  • 2 bathrooms
  • Free WiFi
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  • Air conditioning
  • Stylish and cozy living space featuring a leather sofas, chic decor, and a dining area with patio views.
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  • Exterior Views
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Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub

  • 4 guests
  • 2 bedrooms
  • 2 bathrooms
  • Swimming pool
  • Free WiFi
  • Kitchen
  • Cozy and spacious rustic barn retreat with modern comforts, perfect for a relaxing getaway in nature.
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  • The living area features a large sectional sofa, flat-screen TV, foosball table, and cozy lounge chairs in an open, wood-beamed space.
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Scribe's Stable | A/C • Screened Porch • Sleeps 6

  • 6 guests
  • 2 bedrooms
  • 1 bathroom
  • Free WiFi
  • Air conditioning
  • Pets allowed
  • A scenic aerial shot reveals the home’s secluded lakeside location, with a private dock nestled among dense trees and boats enjoying the water.
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  • Lake Garfield is perfect for swimming, kayaking, and relaxing by the shore.
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Forest Hollow | Waterfront • Kayaks • Wood Stove

  • 6 guests
  • 3 bedrooms
  • 1 bathroom
  • Free WiFi
  • Kitchen
  • Pets allowed
  • A bright and spacious living area with a large leather sectional, and floor-to-ceiling windows overlooking the trees.
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  • Ski the slopes at Catamount, with trails for every level.
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Gilbert Ski Chalet | 3 min to Catamount!

  • 8 guests
  • 3 bedrooms
  • 3 bathrooms
  • Free WiFi
  • Kitchen
  • Washing Machine
  • Open-concept living room with multiple sofas, TV, and wraparound windows offering scenic views.
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  • Outdoor dining area for six and two sun beds to relax with the beautiful view of the lake.
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Bidwell Landing | Lakefront • Spacious

  • 8 guests
  • 4 bedrooms
  • 4 bathrooms
  • Free WiFi
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  • Air conditioning
  • Beautiful Victorian-style home with a covered porch, flower beds, and a classic architectural design.
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  • Celebrate fall with giant pumpkins, live music, and seasonal fun at Saratoga Pumpkin Festival.
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The Gas Lantern | Walk to downtown

  • 4 guests
  • 2 bedrooms
  • 2 bathrooms
  • Free WiFi
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  • Air conditioning
  • Cozy, sun-filled living room featuring a fireplace, plush sectional sofa, and expansive windows offering serene views of the outdoors.
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  • Comfortable seating area perfect for relaxed gatherings, with ceiling fan and large windows for natural light.
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Pothul Perch | Walk to Lake • sleeps 8

  • 8 guests
  • 4 bedrooms
  • 2 bathrooms
  • Free WiFi
  • Kitchen
  • Suitable for children
  • Scenic lakefront view with private dock perfect for canoeing or simply unwinding by the water.
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  • Explore over 10,000 acres of trails, tranquil Benedict Pond, and the beauty of the Berkshires in this peaceful outdoor escape.
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Garfield Grounds | Lakeside • Guest Cottage • Dock

  • 10 guests
  • 4 bedrooms
  • 3 bathrooms
  • Free WiFi
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  • Washing Machine
  • Chic, open-concept living room with vaulted, beamed ceilings, a grand stone fireplace, and cozy modern furnishings accented by warm textures.
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  • Spend the day on the slopes at Butternut Ski Area, a family-friendly mountain close to your stay.
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Jug End Crest | Fireplace • Sunroom • Central Air

  • 6 guests
  • 3 bedrooms
  • 2 bathrooms
  • Free WiFi
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  • Air conditioning
  • Bright open-concept living room with vaulted wood ceilings, spiral staircase to loft, two accent armchairs, and a view toward the dining area for 8 and kitchen.
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  • Experience stunning autumn colors reflected on the reservoir’s waters, a classic New England fall scene.
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Lakeview Luxe | Water Access • Game Room

  • 8 guests
  • 4 bedrooms
  • 2 bathrooms
  • Kitchen
  • Washing Machine
  • Pets allowed
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  • A lively small town filled with cozy coffee shops, boutique shopping, local art galleries, and farm-to-table dining.
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Hupi Hills | town beach • Kayaks • shared court's

  • 6 guests
  • 3 bedrooms
  • 3 bathrooms
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  • Washing Machine
  • Expansive windows flood the interior with light and offer stunning views
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  • Spacious open-concept living area featuring warm wood-paneled ceilings, patterned tile flooring, and red leather sofas arranged around a coffee table, with dining space visible in the background.
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Friendly Hills | Passive Home • EV Charger

  • 6 guests
  • 3 bedrooms
  • 2 bathrooms
  • Free WiFi
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  • Air conditioning
  • Cozy living room featuring a stunning floor-to-ceiling stone fireplace with mounted TV, perfect for relaxing after a day of adventures.
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  • The historic Red Lion inn dating back to the 18th century, known for its warm hospitality, antique charm, and cozy atmosphere in the heart of Stockbridge.
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Mac Shores | 5 min to Tanglewood ! • Shared Beach

  • 6 guests
  • 3 bedrooms
  • 1 bathroom
  • Free WiFi
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  • Charming lakefront cabin surrounded by tall pines, featuring a rustic wood façade and a welcoming front path.
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  • Discover miles of scenic trails, Benedict Pond, and abundant wildlife in this peaceful 10,000-acre forest, perfect for hiking, swimming, and outdoor adventures.
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Goose Pond Landings | Private Dock • Kayaks

  • 6 guests
  • 3 bedrooms
  • 3 bathrooms
  • Free WiFi
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  • Charming cabin exterior with spacious deck and surrounding greenery.
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  • Private lakefront access with a dock, perfect for swimming, fishing, or simply enjoying the view.
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Stockbridge Landings | 3 Mins To Tanglewood

  • 6 guests
  • 3 bedrooms
  • 2 bathrooms
  • Free WiFi
  • Kitchen
  • Air conditioning
  • Rustic-modern dining area with high ceilings, comfortable seating, and plenty of natural light.
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  • Relax and unwind on the deck surrounded by serene woodland views
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Pixley Forest | 15 Mins To Tanglewood • Fireplace

  • 8 guests
  • 4 bedrooms
  • 2 bathrooms
  • Free WiFi
  • Kitchen
  • Air conditioning
  • Enclosed porch with cozy chairs and panoramic window views.
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  • A scenic lake surrounded by rolling hills, ideal for boating, swimming, and enjoying nature year-round.
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St Anne's Manor | Walk to Downtown! • Sleeps 8

  • 8 guests
  • 5 bedrooms
  • 3 bathrooms
  • Kitchen
  • Washing Machine
  • Street parking