Book Guest Houses in Windsor, MA
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Top Guest Houses in Windsor
Hideaway Inn Lenox
11 Old Stockbridge Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $211 total per night
$211 total
Aug 16 - Aug 17
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and picnic area. A communal living room, a library, and a virtual front desk are also on offer.
Pet friendly
Parking included
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$91 nightly
The price is $102 total per night
$102 total
Sep 3 - Sep 4
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
$166 nightly
The price is $185 total per night
$185 total
Aug 19 - Aug 20
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
$147 nightly
The price is $158 total per night
$158 total
Aug 31 - Sep 1
Total with taxes and fees
This guesthouse includes free WiFi in public areas and a virtual front desk.
Free WiFi
Air conditioning
In town, newly remodeled studio with private balcony
Shelburne Falls MA
$150 nightly
The price is $168 total per night
$168 total
Sep 1 - Sep 2
Total with taxes and fees
Free WiFi in public areas and a garden are available at this guesthouse.
Free WiFi
Air conditioning
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$206 nightly
The price is $230 total per night
$230 total
Aug 31 - Sep 1
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
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
Cliffwood Cottage by Evergreen Home
Lenox MA
This guesthouse features laundry facilities.
Free WiFi
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
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 Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
$119 nightly
The price is $133 total per night from Sep 14 to Sep 15
$133 total
Sep 14 - Sep 15
Total with taxes and fees
9.4/10 Exceptional! (160 reviews)
Windsor Guest Houses essential information
Accommodation | 12 Guest Houses |
|---|---|
Lowest Price | $68 |
Highest Price | $230 |
Popular accommodation | Hideaway Inn Lenox, The Central Downtown Inn & Suites, The Revival House, Blooming Inn, In town, newly remodeled studio with private balcony , Berkshire Village Carriage House - Super Private!!, The Dewey, Hill Ross Guest Suite on Historic Homestead, Cliffwood Cottage by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge, Orchard Guest House: Cozy Berkshire Retreat in the Woods |
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