Compare Pittsfield 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 Pittsfield
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$99 nightly
The price is $111 total per night
$111 total
Nov 1 - Nov 2
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
Hideaway Inn Lenox
11 Old Stockbridge Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $146 total per night
$146 total
Nov 3 - Nov 4
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 TV in a common area, and a vending machine.
Pet friendly
Parking included
The Revival House
17 Commercial St Adams MA
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $168 total per night
$168 total
Nov 1 - Nov 2
Total with taxes and fees
The Revival House features free WiFi in public areas and a communal living room. There's free parking if you drive.
Breakfast included
Parking included
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$189 nightly
The price is $211 total per night
$211 total
Oct 29 - Oct 30
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
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
Hudson valley and The Berkshires Cottage
Hillsdale NY
At this guesthouse, guests have access to a garden.
Pet friendly
Free WiFi
Renovated Private Guest House by Evergreen Home
Great Barrington MA
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
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 Pittsfield
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$118 nightly
The price is $132 total per night from Nov 9 to Nov 10
$132 total
Nov 9 - Nov 10
Total with taxes and fees
9/10 Wonderful! (1,239 reviews)
Hotel On North
297 North Street Pittsfield MA
$128 nightly
The price is $143 total per night from Nov 8 to Nov 9
$143 total
Nov 8 - Nov 9
Total with taxes and fees
9.6/10 Exceptional! (967 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
$101 nightly
The price is $113 total per night from Nov 15 to Nov 16
$113 total
Nov 15 - Nov 16
Total with taxes and fees
Pittsfield Guest Houses essential information
Accommodation | 11 Guest Houses |
|---|---|
Lowest Price | $111 |
Highest Price | $211 |
Popular accommodation | The Central Downtown Inn & Suites, Hideaway Inn Lenox, The Revival House, Berkshire Village Carriage House - Super Private!!, The Dewey, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Cliffwood Cottage by Evergreen Home, Chestnut Lodge |
More to Explore
More to Explore
- Hotels near Pleasant Valley Wilderness Sanctuary
- Hotels near Guido's Marketplace
- Hotels near Kennedy Park
- Hotels near Pittsfield Municipal
- Hotels near Berkshire Museum
- Hotels near Crane Museum of Papermaking
- Hotels near Berkshire Athenaeum
- Hotels near Tanglewood Music Center
- Hotels near Bousquet Ski Area
- Hotels near The Bookstore
- Hotels near Skyline Country Club
- Hotels near Canoe Meadows Wildlife Sanctuary
- Condo Rentals in Hancock
- Cottages in Hancock
- Vacation Homes in Hancock
- Resorts in Hancock
- Apartments in Hinsdale
- B&B in Hinsdale
- Inns in Hinsdale
- Vacation Homes in Hinsdale
- Resorts in Hinsdale
- Farmstay in Lenox
- Condo Rentals in Lenox
- Cottages in Lenox
- Guest Houses in Lenox
- Cheap Hotels in Lenox
- Gay Friendly Hotels in Lenox
- Hotels with Balconies in Lenox
- Hotels with Free Breakfast in Lenox
- Hotels with Hot Tubs in Lenox
- Ski Resorts & in Lenox
- Spa Resorts & in Lenox
- Lenox Hotels
- Inns in Lenox
- Villas in Lenox
- Hotels near Hancock Shaker Village
- Cabin Rentals in Berkshire County
- Cottages in Berkshire County
- Country Houses in Berkshire County
- Extended Stay Hotels in Berkshire County
- Arcade Hotels in Berkshire County
- Cheap Hotels in Berkshire County
- Hotels with Airport Transfers in Berkshire County
- Hotels with Pool in Berkshire County
- Hotels with Air Conditioning in Berkshire County
- Hotels with a Gym in Berkshire County
- Hotels with Free Parking in Berkshire County
- Hotels with Kitchenettes in Berkshire County
- Hotels on the Lake in Berkshire County
- Hotels on the River in Berkshire County
- Hotels with Shopping in Berkshire County
- 5 Star Hotels in Dalton
- Cabin Rentals in Dalton
- Dalton Hotels
- Motels in Dalton
- Vacation Homes in Dalton
- Resorts in Dalton
- Hotels near Lenox Library
- Hotels near Herman Melville's Arrowhead
- 4 Star Hotels in Lanesborough
- Farmstay in Lanesborough
- B&B in Lanesborough
- Cabin Rentals in Lanesborough
- Condo Rentals in Lanesborough
- Cottages in Lanesborough
- Guest Houses in Lanesborough
- Hotels with Free Parking in Lanesborough
- Luxury Hotels in Lanesborough
- Ski Resorts & in Lanesborough
- Lanesborough Hotels
- Vacation Homes in Lanesborough
- Hotels near Barrington Stage Company
- Flights from Pittsfield Municipal
- Flights from Pittsburgh (AGC) to Pittsfield (PSF)
- Flights from Oranjestad (AUA) to Pittsfield (PSF)
- Flights from Araguaina (AUX) to Pittsfield (PSF)
- Flights from Biak (BIK) to Pittsfield (PSF)
- Flights from Nashville (BNA) to Pittsfield (PSF)
- Flights from Coimbatore (CJB) to Pittsfield (PSF)
- Flights from Kannur (CNN) to Pittsfield (PSF)
- Flights from Charleville (CTL) to Pittsfield (PSF)
- Flights from East London (ELS) to Pittsfield (PSF)
- Flights from El Aaiun (EUN) to Pittsfield (PSF)
- Flights from Atyrau (GUW) to Pittsfield (PSF)
- Flights from Washington (IAD) to Pittsfield (PSF)
- Flights from Imperatriz (IMP) to Pittsfield (PSF)
- Flights from Manchester (MAN) to Pittsfield (PSF)
- Flights from Chicago (ORD) to Pittsfield (PSF)
- Flights from Puerto Maldonado (PEM) to Pittsfield (PSF)
- Flights from Fort Myers (RSW) to Pittsfield (PSF)
- Flights from Salt Lake City (SLC) to Pittsfield (PSF)
- Flights from Tirana (TIA) to Pittsfield (PSF)
- Flights to Lenox
- Flights from Miami to Lenox
- Flights from Newark to Lenox
- Flights to Berkshire County
- Flights from Lanesborough