Compare Pittsfield Guest House Rentals

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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
$85 nightly
The price is $95 total per night
$95 total
Nov 30 - Dec 1
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
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$189 nightly
The price is $211 total per night
$211 total
Nov 30 - Dec 1
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
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 30 - Dec 1
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
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
$305 nightly
The price is $310 total per night
$310 total
Dec 17 - Dec 18
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has 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, a garden, and barbecue grills.
Pet friendly
Free WiFi
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd Lee MA
Guests staying at Jacob's Tanglewood Ranch enjoy free WiFi in public areas, a terrace, and a fireplace in the lobby. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a picnic area.
Pet friendly
Parking included
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
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
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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
    $120 nightly
    The price is $135 total per night from Dec 7 to Dec 8
    $135 total
    Dec 7 - Dec 8
    Total with taxes and fees
    9/10 Wonderful! (763 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $89 nightly
    The price is $100 total per night from Nov 29 to Nov 30
    $100 total
    Nov 29 - Nov 30
    Total with taxes and fees
    7.8/10 Good! (962 reviews)
    Hotel On North

    Hotel On North

    297 North Street Pittsfield MA
    $133 nightly
    The price is $149 total per night from Dec 22 to Dec 23
    $149 total
    Dec 22 - Dec 23
    Total with taxes and fees
    9.4/10 Exceptional! (799 reviews)

Pittsfield Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
$95
Highest Price
$310
Popular accommodation
The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Revival House, The Dewey, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home

More to Explore