Compare Hillsdale Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in Hillsdale
Hideaway Inn Lenox
11 Old Stockbridge Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $211 total per night
$211 total
Aug 26 - Aug 27
Total with taxes and fees
At Hideaway Inn Lenox, guests have access to free WiFi in public areas, microwave in a common area, and an arcade/game room. Free parking is available if you drive. Other amenities at this family-friendly guesthouse include a library, a communal living room, and a picnic area.
Pet friendly
Parking included
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$99 nightly
The price is $111 total per night
$111 total
Aug 26 - Aug 27
Total with taxes and fees
Guests of The Central Downtown Inn & Suites enjoy free WiFi in public areas, express check-in, and express check-out. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide luggage storage. Additional amenities include a terrace and laundry facilities.
Pet friendly
Parking included
The Harlow House
439 Lake Dr Rhinebeck NY
$175 nightly
The price is $198 total per night
$198 total
Sep 1 - Sep 2
Total with taxes and fees
Guests staying at The Harlow House enjoy free WiFi in public areas, a terrace, and a water dispenser. You can take advantage of free parking if you drive. Additional amenities include a garden and a picnic area.
Parking included
Free WiFi
9 Academy
9 Academy St Salisbury CT
$594 nightly
The price is $683 total per night
$683 total
Sep 13 - Sep 14
Total with taxes and fees
9 Academy features free WiFi in public areas, express check-in, and express check-out. You can put free parking to good use if you drive. Additional amenities include laundry facilities and a garden.
Parking included
Free WiFi
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$189 nightly
The price is $211 total per night
$211 total
Aug 31 - Sep 1
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
Hits | Catskills Views | Pet Friendly | Studio
Saugerties NY
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has a garden.
Free WiFi
Air conditioning
The Dewey
7 Hubbard Street Lenox MA
At The Dewey, guests have access to free WiFi in public areas, a meeting room, and a library. If you plan to drive, free parking is available. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include express check-out, free newspapers, and a terrace.
Parking included
Free WiFi
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.
Hotel Options in Hillsdale
The Yankee Inn
461 Pittsfield Rd Lenox MA
$158 nightly
The price is $176 total per night from Sep 14 to Sep 15
$176 total
Sep 14 - Sep 15
Total with taxes and fees
9.2/10 Wonderful! (1,021 reviews)
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$125 nightly
The price is $139 total per night from Aug 31 to Sep 1
$139 total
Aug 31 - Sep 1
Total with taxes and fees
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
$61 nightly
The price is $68 total per night from Aug 27 to Aug 28
$68 total
Aug 27 - Aug 28
Total with taxes and fees
Hillsdale Guest Houses essential information
Accommodation | 16 Guest Houses |
|---|---|
Lowest Price | $68 |
Highest Price | $683 |
Popular accommodation | Hideaway Inn Lenox, The Central Downtown Inn & Suites, The Harlow House, 9 Academy , Berkshire Village Carriage House - Super Private!!, Hits | Catskills Views | Pet Friendly | Studio, The Dewey, Hudson valley and The Berkshires Cottage, LEEDS A GREAT ESCAPE |