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

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$97 nightly
The price is $109 total per night
$109 total
Nov 12 - Nov 13
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

Hideaway Inn Lenox

2 out of 5
11 Old Stockbridge Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $151 total per night
$151 total
Nov 16 - Nov 17
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 picnic area, and a communal living room.
Pet friendly
Parking included
The Revival House

The Revival House

3 out of 5
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 15 - Nov 16
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!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$180 nightly
The price is $201 total per night
$201 total
Nov 15 - Nov 16
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
The Dewey

The Dewey

3.5 out of 5
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

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

Renovated Private Guest House by Evergreen Home

Great Barrington MA
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Pet friendly
Free WiFi
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

Lenox MA
At this guesthouse, guests have access to features like laundry facilities.
Free WiFi
Air conditioning
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
At Chestnut Lodge, guests have access to free WiFi in public areas, a hot tub, and a terrace. A stay here includes free parking. This smoke-free guesthouse also has a picnic area.
Hot Tub
Parking included
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $108 nightly
    The price is $120 total per night from Dec 10 to Dec 11
    $120 total
    Dec 10 - Dec 11
    Total with taxes and fees
    Hotel On North

    Hotel On North

    297 North Street Pittsfield MA
    $112 nightly
    The price is $125 total per night from Nov 29 to Nov 30
    $125 total
    Nov 29 - Nov 30
    Total with taxes and fees
    Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

    Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

    1055 South Street Pittsfield MA
    $110 nightly
    The price is $123 total per night from Nov 15 to Nov 16
    $123 total
    Nov 15 - Nov 16
    Total with taxes and fees

Pittsfield Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$109
Highest Price
$201
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