A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Hillsdale guest houses

A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

1. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (70 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 AU$164
includes taxes & fees
19 Nov - 20 Nov
Hideaway Inn Lenox
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (436 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is AU$157
includes taxes & fees
11 Nov - 12 Nov
The Central Downtown Inn & Suites
A modern bedroom with a large bed, a red sofa, a fireplace, and a television.

3. The Harlow House

The Harlow House
2.0 star property
Rhinebeck
8.8 out of 10, Excellent, (23 reviews)
"Great place"
United States
Robert
The price is AU$316
includes taxes & fees
12 Nov - 13 Nov
The Harlow House
A modern kitchen with a dining area, a large window, and a view of the garden.

4. 9 Academy

9 Academy
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (15 reviews)
"Incredible space. I plan on staying again anytime I’m in the area. Wonderful staff, very easy check in and check out. Excellent room and amenities."
United States
Kyle
The price is AU$987
includes taxes & fees
29 Nov - 30 Nov
9 Academy
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

5. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (302 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
The price is AU$289
includes taxes & fees
15 Nov - 16 Nov
Berkshire Village Carriage House - Super Private!!
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 Hillsdale Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Great place in walking distance to city center. Excellent customer service and kind, helpful staff. Clean rooms and a full breakfast included."
Kiana 1-night trip
Posted 3 hours ago
Quality Inn Great Barrington

Find out more about Hillsdale

Hillsdale Guest Houses information

Number of reviews
776
Accommodation
16 Guest Houses
Lowest Price
AU$157
Highest Price
AU$987