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Holiday rentals in Western Massachusetts

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Top-rated holiday rentals in Western Massachusetts

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage in Orange
The Lake Cottage: A Sweetwater Stay
Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC. 35 mins to the Berkshires.
₹8,017 per night
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Cabin in North Adams
Mahican Cabin - A Private Nature's Reserve For 2
The Mahican Cabin is at the highest peak of the Hoosac Range known as western summit and borders 750 acres of protected land so social distancing is not a problem. Enjoy the modern comforts of a real bed (memory foam mattress), A/C (or heat), in cabin mini fridge, and a full bath inside the cabin. A deck overlooking the most amazing Berkshires Sunset. Hang out at your own hammock, make s'mores the way you used to and grill a perfect steak to complete the day! It's a nature's retreat for 2.
₹20,131 per night
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Chalet in Otis
Mid-Century Glass Octagon Chalet in Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior. You can cozy up around the wood-burning fireplace, while gazing through the floor to ceiling windows onto the serenely private seven acres, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving the property. Up to you!
₹25,395 per night
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Other great holiday rentals in Western Massachusetts

Treehouse in Lee
Gingerbread House Tower in the Berkshire Hills
₹22,909 per night
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Rental unit in Shelburne Falls
In town, newly renovated studio with private deck
₹7,761 per night
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Home in Chester
Riverfront Getaway
₹11,355 per night
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Tiny home in Orange
The Photographer's Hut: A Sweetwater Stay
₹7,854 per night
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Guest house in Northampton
Mill River Cottage (pet friendly!)
₹8,578 per night
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Cottage in Becket
Cozy lakeside cottage
₹5,672 per night
Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
₹20,540 per night
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Guest house in Amherst
Cozy get-away!
₹7,737 per night
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Loft in Shelburne Falls
Secret Corner of Shelburne Falls
₹7,539 per night
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Home in Northampton
The Farmhouse - Eclectic country home with hot tub
₹17,774 per night
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Home in New Lebanon
The old sawmill from 1771
₹8,665 per night
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Cottage in Becket
Berkshires Modern Comfy Private Retreat! Hot tub!
₹7,131 per night