A lake surrounded by autumn-colored trees and hills.

Search Guest Houses in Cheshire from CA $151

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Cheshire guest houses

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (428 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is CA $139
CA $155 total
includes taxes & fees
Oct 27 - Oct 28
The Central Downtown Inn & Suites
A living room with a fireplace, two sofas, and four black side tables.

2. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (42 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
The price is CA $193
CA $216 total
includes taxes & fees
Nov 2 - Nov 3
The Revival House
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

3. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (301 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
The price is CA $189
CA $294 total
includes taxes & fees
Oct 26 - Oct 27
Berkshire Village Carriage House - Super Private!!
A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

4. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (64 reviews)
"Although the property was vintage, the rooms were clean and staff were very helpful and fun to be around. Parking and breakfast were included and the location was excellent."
United States
Barbara
The price is CA $135
CA $151 total
includes taxes & fees
Nov 17 - Nov 18
Hideaway Inn Lenox
A two-story house with a porch, a balcony, and a chimney.

5. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (151 reviews)
"Like the ambiance as well as the decor! The location was perfect for walking around town!"
United States
Robert
The price is CA $100
CA $180 total
includes taxes & fees
Oct 25 - Oct 26
Blooming Inn
A wooden deck with two black wicker chairs and a small round table with a white vase.

6. In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (135 reviews)
"Nice little studio in a pretty little town. Had a great stay."
United States
Apoorva
The price is CA $207
CA $307 total
includes taxes & fees
Oct 28 - Oct 29
In town, newly remodeled studio with private balcony
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very nice place. Rooms are large and always clean. Pool is a nice perk"
Julie 2-night trip
Posted 4 hours ago
Berkshire Mountain Lodge

Find out more about Cheshire

Cheshire Guest Houses information

Number of reviews
778
Accommodation
11 Guest Houses
Lowest Price
CA $151
Highest Price
CA $307

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