Book Guest Houses in Windsor, MA
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Top Guest Houses in Windsor
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$106 nightly
The price is $118 total per night
$118 total
May 31 - Jun 1
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.
Pet friendly
Parking included
The Revival House
17 Commercial St Adams MA
Free Cancellation
Reserve now, pay when you stay
$173 nightly
The price is $193 total per night
$193 total
May 10 - May 11
Total with taxes and fees
This guesthouse features free WiFi in public areas, a virtual front desk, and free self parking. Enjoy the free self-serve breakfast each morning. A communal living room is also provided.
Breakfast included
Parking included
Blooming Inn
22 Mechanic St Shelburne Falls MA
$150 nightly
The price is $162 total per night
$162 total
May 9 - May 10
Total with taxes and fees
This guesthouse includes free WiFi in public areas and a virtual front desk.
Free WiFi
Air conditioning
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$189 nightly
The price is $211 total per night
$211 total
May 10 - May 11
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
In town, newly remodeled studio with private balcony
Shelburne Falls MA
$160 nightly
The price is $179 total per night
$179 total
Jun 4 - Jun 5
Total with taxes and fees
Free WiFi in public areas and a garden are available at this guesthouse.
Free WiFi
Air conditioning
The Dewey
7 Hubbard Street Lenox MA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
Hill Ross Guest Suite on Historic Homestead
Florence MA
This guesthouse features a garden, laundry facilities, and barbecue grills.
Breakfast included
Air conditioning
Jacob's Tanglewood Ranch
560 Stockbridge Rd Lee MA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and a communal living room are also on offer.
Pet friendly
Parking included
Cliffwood Cottage by Evergreen Home
Lenox MA
This guesthouse features laundry facilities.
Free WiFi
Air conditioning
Chestnut Lodge
75 Chestnut Street Lee MA
A hot tub is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A terrace and a picnic area are also provided.
Hot Tub
Parking included
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.
Top hotels in Windsor
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$145 nightly
The price is $162 total per night from May 11 to May 12
$162 total
May 11 - May 12
Total with taxes and fees
9.2/10 Wonderful! (890 reviews)
Windsor Guest Houses essential information
Accommodation | 9 Guest Houses |
|---|---|
Lowest Price | $110 |
Highest Price | $211 |
Popular accommodation | The Central Downtown Inn & Suites, The Revival House, Blooming Inn, Berkshire Village Carriage House - Super Private!!, In town, newly remodeled studio with private balcony , The Dewey, Hill Ross Guest Suite on Historic Homestead, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge, Orchard Guest House: Cozy Berkshire Retreat in the Woods |
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