Compare Stockbridge Guest House Rentals
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Featured Guest Houses in Stockbridge
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$85 nightly
The price is $95 total per night
$95 total
Dec 22 - Dec 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
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$188 nightly
The price is $210 total per night
$210 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
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
Hudson valley and The Berkshires Cottage
Hillsdale NY
$307 nightly
The price is $312 total per night
$312 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has a garden.
Pet friendly
Free WiFi
Renovated Private Guest House by Evergreen Home
Great Barrington MA
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Pet friendly
Free WiFi
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
1805 House Bed and Breakfast
775 Snydertown Road Craryville NY
Guests staying at 1805 House Bed and Breakfast have access to a terrace, a garden, and a picnic area. You can put free parking to good use if you drive. Multilingual staff is on hand to answer questions.
Breakfast included
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 Stockbridge
The Red Lion Inn
30 Main Street Stockbridge MA
$180 nightly
The price is $202 total per night from Jan 14 to Jan 15
$202 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
$414 nightly
The price is $462 total per night from Jan 5 to Jan 6
$462 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.2/10 Wonderful! (85 reviews)
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night from Jan 4 to Jan 5
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (2,174 reviews)
Stockbridge Guest Houses essential information
Accommodation | 10 Guest Houses |
|---|---|
Lowest Price | $95 |
Highest Price | $462 |
Popular accommodation | The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, 1805 House Bed and Breakfast , Chestnut Lodge, Cliffwood Cottage by Evergreen Home |