Book Guest Houses in Hillsdale
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Featured Guest Houses in Hillsdale

The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
The price is CA $140 per night
CA $140
CA $156 total
Nov 9 - Nov 10
includes taxes & fees
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located nearby.

Hideaway Inn Lenox
11 Old Stockbridge Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $150 per night
CA $150
CA $168 total
Nov 9 - Nov 10
includes taxes & fees
Book a stay at this family-friendly guesthouse in Lenox. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.

The Harlow House
439 Lake Dr Rhinebeck NY
The price is CA $279 per night
CA $279
CA $316 total
Dec 3 - Dec 4
includes taxes & fees
Stay at this guesthouse in Rhinebeck. Enjoy free WiFi, free parking, and a garden. Popular attractions Northern Dutchess Botanical Gardens and Center for Performing Arts at Rhinebeck are located nearby.

Berkshire Village Carriage House - Super Private!!
Lanesborough MA
The price is CA $212 per night
CA $212
CA $309 total
Nov 15 - Nov 16
includes taxes & fees
Stay at this guesthouse in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Pontoosuc Lake are located nearby.

LEEDS A GREAT ESCAPE
Leeds NY
Stay at this guesthouse in Catskill. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Catskill Golf Club and Thomas Cole National Historic Site are located nearby.

Hits | Catskills Views | Pet Friendly | Studio
Saugerties NY
Stay at this guesthouse in Saugerties. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions HITS-on-the-Hudson and George J. Terpening Sr. Memorial Park are located nearby.

The Dewey
7 Hubbard Street Lenox MA
Stay at this guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.

9 Academy
9 Academy St Salisbury CT
The price is CA $805 per night
CA $805
CA $926 total
Dec 8 - Dec 9
includes taxes & fees
Stay at this guesthouse in Salisbury. Enjoy free WiFi, free parking, and a garden. Popular attractions Mount Frissell and Scoville Memorial Library are located nearby.

Hudson valley and The Berkshires Cottage
Hillsdale NY
Stay at this guesthouse in Hillsdale. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Catamount Aerial Adventure Park and Art et Industrie are located nearby.

Renovated Private Guest House by Evergreen Home
Great Barrington MA
Stay at this guesthouse in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Art et Industrie and Lake Mansfield Park are located nearby.

Cliffwood Cottage by Evergreen Home
Lenox MA
Stay at this guesthouse in Lenox. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
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.
Top trending hotels in Hillsdale

The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is CA $155 per night from Dec 9 to Dec 10
CA $155
CA $173 total
Dec 9 - Dec 10
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
Hillsdale Guest Houses essential information
Accommodation | 16 Guest Houses |
|---|---|
Lowest Price | CA $119 |
Highest Price | CA $926 |
Popular accommodation | The Central Downtown Inn & Suites, Hideaway Inn Lenox, The Harlow House, Berkshire Village Carriage House - Super Private!!, LEEDS A GREAT ESCAPE, Hits | Catskills Views | Pet Friendly | Studio, The Dewey, 9 Academy , Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Cliffwood Cottage by Evergreen Home, Chestnut Lodge |






