Compare Canaan Guest House Rentals
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Featured Guest Houses in Canaan
9 Academy
9 Academy St Salisbury CT
$494 nightly
The price is $568 total per night
$568 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9 Academy features free WiFi in public areas, express check-in, and express check-out. You can put free parking to good use if you drive. Additional amenities include laundry facilities and a garden.
Parking included
Free WiFi
Hudson valley and The Berkshires Cottage
Hillsdale NY
$305 nightly
The price is $310 total per night
$310 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
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 Canaan
The Red Lion Inn
30 Main Street Stockbridge MA
$178 nightly
The price is $199 total per night from Jan 14 to Jan 15
$199 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$145 nightly
The price is $162 total per night from Jan 4 to Jan 5
$162 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (804 reviews)
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
$107 nightly
The price is $120 total per night from Jan 4 to Jan 5
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (708 reviews)
Canaan Guest Houses essential information
Accommodation | 5 Guest Houses |
|---|---|
Lowest Price | $120 |
Highest Price | $568 |
Popular accommodation | 9 Academy , Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge |