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
$99 nightly
The price is $111 total per night
$111 total
Feb 22 - Feb 23
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
Blooming Inn
22 Mechanic St Shelburne Falls MA
$139 nightly
The price is $150 total per night
$150 total
Feb 1 - Feb 2
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
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$188 nightly
The price is $210 total per night
$210 total
Feb 1 - Feb 2
Total with taxes and fees
Guests staying at this guesthouse have access to barbecue grills and a garden.
Free WiFi
Air conditioning
The Revival House
17 Commercial St Adams MA
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $168 total per night
$168 total
Feb 8 - Feb 9
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
The Dewey
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
In town, newly remodeled studio with private balcony
Shelburne Falls MA
$140 nightly
The price is $156 total per night
$156 total
Feb 2 - Feb 3
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 picnic area. You can take advantage of free parking if you drive. Additional amenities include a communal living room and barbecue grills.
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
$126 nightly
The price is $141 total per night from Feb 22 to Feb 23
$141 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (2,219 reviews)
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$126 nightly
The price is $141 total per night from Feb 24 to Feb 25
$141 total
Feb 24 - Feb 25
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$121 nightly
The price is $136 total per night from Mar 1 to Mar 2
$136 total
Mar 1 - Mar 2
Total with taxes and fees
9/10 Wonderful! (822 reviews)
Windsor Guest Houses essential information
Accommodation | 9 Guest Houses |
|---|---|
Lowest Price | $111 |
Highest Price | $210 |
Popular accommodation | The Central Downtown Inn & Suites, Blooming Inn, Berkshire Village Carriage House - Super Private!!, The Revival House, The Dewey, In town, newly remodeled studio with private balcony , Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home |