Compare Windsor Guest House Rentals
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Featured Guest Houses in Windsor
Blooming Inn
22 Mechanic St, Shelburne Falls, MA
$124 nightly
The price is $134 total per night
$134 total
May 11 - May 12
Total includes taxes and fees
Blooming Inn features free WiFi in public areas, coffee in a common area, and refrigerator in a common area. You can put free offsite parking to good use if you drive.
Free WiFi
Air conditioning
The Central Downtown Inn & Suites
20 W Housatonic St., Pittsfield, MA
$109 nightly
The price is $122 total per night
$122 total
May 11 - May 12
Total includes 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
In town, newly remodeled studio with private balcony
$140 nightly
The price is $156 total per night
$156 total
May 12 - May 13
Total includes taxes and fees
This guesthouse features free WiFi in public areas and a garden.
Free WiFi
Air conditioning
Guest House Sanctuary by Evergreen Home
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Free WiFi
Parking available
Jacob's Tanglewood Ranch
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.
Pet friendly
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.
Hotel Options in Windsor
Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
$134 nightly
The price is $150 total per night from May 19 to May 20
$150 total
May 19 - May 20
Total includes taxes and fees
8.6/10 Excellent! (999 reviews)
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
$119 nightly
The price is $133 total per night from May 22 to May 23
$133 total
May 22 - May 23
Total includes taxes and fees
9/10 Wonderful! (573 reviews)
The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
$111 nightly
The price is $123 total per night from May 18 to May 19
$123 total
May 18 - May 19
Total includes taxes and fees
9/10 Wonderful! (1,002 reviews)
Windsor Guest Houses essential information
Accommodation | 6 Guest Houses |
|---|---|
Lowest Price | $122 total |
Highest Price | $156 total |
Popular accommodation | Blooming Inn, The Central Downtown Inn & Suites, In town, newly remodeled studio with private balcony , Guest House Sanctuary by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home |
Guest Houses in Windsor
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