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10 Oct - 12 Oct
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31 Oct - 2 Nov
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28 Nov - 30 Nov

Featured Guest Houses in Cheshire

The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (321)
"Nice place "
The price is AU$177
includes taxes & fees
1 Oct - 2 Oct
The Central Downtown Inn & Suites
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (325)
"Great spot. Lots of history. "
The price is AU$303
includes taxes & fees
30 Sept - 1 Oct
The Dewey
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (113)
"Lovely Inn and very responsive and approachable staff. "
The price is AU$229
includes taxes & fees
5 Oct - 6 Oct
Blooming Inn
The Revival House
Romantic Room, 1 King Bed (Room 4)

The Revival House

3.0 star property
8.8 out of 10, Excellent, (16)
"We thoroughly enjoyed our stay at The Revival House! Super comfortable, clean, and the inside has great decor sensibilities. We will be back if we’re ever in the area again!"
The price is AU$287
includes taxes & fees
30 Sept - 1 Oct
The Revival House
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (259)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is AU$352
includes taxes & fees
30 Sept - 1 Oct
Berkshire Village Carriage House - Super Private!!
In town, newly remodeled studio with private balcony
Smart TV, Netflix, streaming services

In town, newly remodeled studio with private balcony

10.0 out of 10, Exceptional, (117)
"Great place. Quiet, clean and spacious - thank you so much "
The price is AU$242
includes taxes & fees
26 Oct - 27 Oct
In town, newly remodeled studio with private balcony
Jacob's Tanglewood Ranch
Dishwasher

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Chestnut Lodge
Property grounds

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge
Cliffwood Cottage by Evergreen Home
Interior

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Absolutely loved every part of my stay at Hotel North. Parking was so easy and safe. The Hotel is decorated so tastefully, the staff was so welcoming. When I stepped into my room, I felt I had walked into a soothing refuge. Your decorators knew just how to balance the aesthetics with furnishings, art work, etc. Every detail was perfect - the room temperature, the comfortable bed, the quietness, etc. I will definitely recommend the Hotel North to anyone traveling to the Pittsfield area. Good job everyone!"
Jetta 1-night trip
Posted 2 days ago
Hotel On North

Find out more about Cheshire

Find out more about Cheshire

Cheshire Guest Houses information

Number of reviews
1,015
Accommodation
9 Guest Houses
Lowest Price
AU$177
Highest Price
AU$352

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