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

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

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
7.8 out of 10, Good, (60 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 NZ$257
includes taxes & fees
28 Sept - 29 Sept
Hideaway Inn Lenox
A modern bedroom with a large bed, a red sofa, a fireplace, and a television.

2. The Harlow House

The Harlow House
2.0 star property
Rhinebeck
8.8 out of 10, Excellent, (19 reviews)
"Beautiful location in the woods but super close to the charming village of Rhinebeck. The room was spacious and tastefully furnished, comfy bed and linens, fireplace for the winter, lovely deck perfect for morning coffee. Just there one night but it was a lovely stay!"
United States
Lauren
The price is NZ$381
includes taxes & fees
30 Sept - 1 Oct
The Harlow House
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

3. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (415 reviews)
"Large, clean, comfortable suite."
United States
Rena
The price is NZ$195
includes taxes & fees
27 Sept - 28 Sept
The Central Downtown Inn & Suites
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

4. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (295 reviews)
"A cute, quiet getaway close to the Berkshire mountains!"
United States
Maya H.
The price is NZ$367
includes taxes & fees
1 Oct - 2 Oct
Berkshire Village Carriage House - Super Private!!
A modern kitchen with a dining area, a large window, and a view of the garden.

5. 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 NZ$1,206
includes taxes & fees
27 Sept - 28 Sept
9 Academy
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"It’s an older facility , as expected, but with great character and very clean . Special praise goes to the staff , in particular , Michele at the front desk . Super nice and very helpful in answering our questions about the local activities . Will keep in mind for another visit ."
Saed 1-night trip
Posted 6 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Hillsdale

Hillsdale Guest Houses information

Number of reviews
370
Accommodation
16 Guest Houses
Lowest Price
NZ$195
Highest Price
NZ$1,206