Compare Windsor Guest House Rentals
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Featured Guest Houses in Windsor
The Central Downtown Inn & Suites
20 W Housatonic St., Pittsfield, MA
$104 nightly
The price is $116 total per night
$116 total
Oct 31 - Nov 1
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
The Dewey
7 Hubbard Street, Lenox, MA
$184 nightly
The price is $206 total per night
$206 total
Nov 9 - Nov 10
Total with taxes and fees
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
Blooming Inn
22 Mechanic St, Shelburne Falls, MA
$139 nightly
The price is $150 total per night
$150 total
Oct 26 - Oct 27
Total with 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 Revival House
17 Commercial St, Adams, MA
Free Cancellation
Reserve now, pay when you stay
$168 nightly
The price is $188 total per night
$188 total
Oct 13 - Oct 14
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!!
$205 nightly
The price is $229 total per night
$229 total
Oct 28 - Oct 29
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
In town, newly remodeled studio with private balcony
$140 nightly
The price is $156 total per night
$156 total
Oct 26 - Oct 27
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
Free WiFi
Air conditioning
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 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
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
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
$112 nightly
The price is $125 total per night from Nov 2 to Nov 3
$125 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (2,039 reviews)
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
$97 nightly
The price is $108 total per night from Nov 5 to Nov 6
$108 total
Nov 5 - Nov 6
Total with taxes and fees
8.8/10 Excellent! (678 reviews)
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
$129 nightly
The price is $144 total per night from Nov 2 to Nov 3
$144 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (749 reviews)
Windsor Guest Houses essential information
Accommodation | 9 Guest Houses |
|---|---|
Lowest Price | $108 |
Highest Price | $229 |
Popular accommodation | The Central Downtown Inn & Suites, The Dewey, Blooming Inn, The Revival House, Berkshire Village Carriage House - Super Private!!, In town, newly remodeled studio with private balcony , Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home |