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Vacation rentals in Cherry Plain

Vacation rentals in Cherry Plain

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cherry Plain

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

  • Berkshire Guest Suite
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bathroom
    Berkshire Guest Suite

    Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

    What guests are saying:

    “We were very pleased with our stay at Dave and Ashley’s. We had done some hiking in the area and we were far enough from home where we made a fun little trip out of it to stay in the area for the night. Very beautifully decorated and comfortable. Great added touches with snacks, coffee, mini fridge, toiletries, TV, and more. Beautiful neighborhood and view of the mountains. Will definitely be back in the future!”

  • The Beer Diviner Brewery Apartment
    SUPERHOSTEntire flat · 3 guests · 2 beds · 1 bathroom
    The Beer Diviner Brewery Apartment

    Whole upstairs space 14 x 28 feet, small bathroom with claw foot tub and shower, twin and a full size bed, High def TV with blu ray movies, private deck, small fridge and microwave, complimentary tea and coffee (no breakfast). Complimentary pint downstairs at the brewery and taproom. Located in a private setting in a hollow in the Taconic Mountains

    What guests are saying:

    “We stayed here for Tuesday/Wednesday nights so the bar wasn't open and I can't speak to experiencing that. The place was nice and as expected, the location was near a few parks and that was great. It was missing paper towels the first night however he brought some in for the second night. A couple wasps came in (they weren't an aggressive species) and he offered to come and kill them when we mentioned them to him, but they were easy enough to take care of. It wasn't ideal for cooking in the room (only a microwave) but there was dish soap and a sponge in the bathroom. Coffee cups and a Kuerig were there, so that was super nice. Overall it does the job if you're looking for a place in the woods!”

  • The Writer's Cottage
    SUPERHOSTEntire cottage · 3 guests · 2 beds · 1 bathroom
    The Writer's Cottage

    The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Find an airy loft up narrow enclosed stairs for some extra space. Orchard and lawn outside. Also -- we put three days in between stays.

    What guests are saying:

    “What a wonderful stay! We were unsure if the place was going to be too small but not at all! We had the perfect space for two adults and the little toddler. The apartment was very clean with AMAZING TOUCHES! We found apples, eggs, coffee for us in the fridge! So nice. Kitchen is well equipped with everything you need (incl condiments). Bathroom will several body wash, shampoos. Last but not least, our LO had everything he needed: crib&high chair! About location. Same as the mill, perfectly located to discover the Berkshires! Will definitely come back again!”

Holiday rentals for every style

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Popular amenities for Cherry Plain holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Cherry Plain

Berkshires Waterfront Lakehouse
Entire cottage
Berkshires Waterfront Lakehouse
Price:€199 / night
Private Cottage in the Berkshires
SUPERHOSTEntire guest house
Private Cottage in the Berkshires
Price:€84 / night
Vermont Shared Artist Guesthouse -Francis room
SUPERHOSTPrivate room
Vermont Shared Artist Guesthouse -Francis room
Price:€49 / night
Stone School Cottage
SUPERHOSTEntire house
Stone School Cottage
Price:€124 / night
Cozy barn apartment on the river
SUPERHOSTEntire flat
Cozy barn apartment on the river
Price:€115 / night
Bright Guest House with Mountain Views
SUPERHOSTEntire guest house
Bright Guest House with Mountain Views
Price:€133 / night
Sweet Brookside Cottage
SUPERHOSTEntire cottage
Sweet Brookside Cottage
Price:€64 / night
Cute Cozy Comfy Cottage in the Berkshires
SUPERHOSTEntire cottage
Cute Cozy Comfy Cottage in the Berkshires
Price:€111 / night
Star Gazer Farm
SUPERHOSTEntire guest suite
Star Gazer Farm
Price:€133 / night
The Sail Loft
SUPERHOSTEntire cottage
The Sail Loft
Price:€75 / night
Cozy riverside cottage near stocked markets.  --
Entire cottage
Cozy riverside cottage near stocked markets. --
Price:€119 / night
Private Suite in the Beautiful Berkshires
SUPERHOSTEntire guest suite
Private Suite in the Beautiful Berkshires
Price:€106 / night
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