Compare The Berkshires Guest House Rentals

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Featured Guest Houses in The Berkshires

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$99 nightly
The price is $111 total per night
$111 total
Oct 5 - Oct 6
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
$140 nightly
The price is $156 total per night
$156 total
Oct 26 - Oct 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 picnic area, and a TV in a common area.
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 2 - Nov 3
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
$189 nightly
The price is $211 total per night
$211 total
Oct 4 - Oct 5
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
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
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
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
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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 The Berkshires

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $110 nightly
    The price is $123 total per night from Nov 1 to Nov 2
    $123 total
    Nov 1 - Nov 2
    Total with taxes and fees
    8.8/10 Excellent! (2,691 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $108 nightly
    The price is $120 total per night from Nov 1 to Nov 2
    $120 total
    Nov 1 - Nov 2
    Total with taxes and fees
    Quality Inn Great Barrington

    Quality Inn Great Barrington

    372 Main Street Great Barrington MA
    $76 nightly
    The price is $85 total per night from Nov 1 to Nov 2
    $85 total
    Nov 1 - Nov 2
    Total with taxes and fees
    8.6/10 Excellent! (1,000 reviews)

The Berkshires Guest Houses essential information

Accommodation
9 Guest Houses
Lowest Price
$85
Highest Price
$211
Popular accommodation
The Central Downtown Inn & Suites, Hideaway Inn Lenox, The Revival House, Berkshire Village Carriage House - Super Private!!, The Dewey, Renovated Private Guest House by Evergreen Home, Cliffwood Cottage by Evergreen Home, Chestnut Lodge, Jacob's Tanglewood Ranch

More to Explore