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
$102 nightly
The price is $114 total per night
$114 total
Apr 12 - Apr 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
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$185 nightly
The price is $207 total per night
$207 total
Apr 12 - Apr 13
Total with taxes and fees
Guests staying at this guesthouse have access to barbecue grills and a garden.
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
Apr 12 - Apr 13
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.
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

Hillsdale NY
$308 nightly
The price is $311 total per night
$311 total
Apr 20 - Apr 21
Total with taxes and fees
At this guesthouse, guests have access to a garden.
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.
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.
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 picnic area. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a fireplace in the lobby.
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

Lenox MA
At this guesthouse, guests have access to features like laundry facilities.
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
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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
    $108 nightly
    The price is $120 total per night from May 10 to May 11
    $120 total
    May 10 - May 11
    Total with taxes and fees
    9/10 Wonderful! (897 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $118 nightly
    The price is $132 total per night from May 10 to May 11
    $132 total
    May 10 - May 11
    Total with taxes and fees
    8/10 Very Good! (1,001 reviews)
    Hotel On North

    Hotel On North

    297 North Street Pittsfield MA
    $149 nightly
    The price is $166 total per night from Apr 12 to Apr 13
    $166 total
    Apr 12 - Apr 13
    Total with taxes and fees
    9.6/10 Exceptional! (843 reviews)

Pittsfield Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
$114
Highest Price
$311
Popular accommodation
The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Revival House, Hudson valley and The Berkshires Cottage, The Dewey, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge

More to Explore