Book Guest Houses in Great Barrington
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Featured Guest Houses in Great Barrington
The Central Downtown Inn & Suites
20 W Housatonic St., Pittsfield, MA
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located nearby.
Pet-friendly
Parking included
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
The price is CA $166 per night
CA $166
CA $349 total
includes taxes & fees
26 Dec - 27 Dec
Stay at this guesthouse in North Granby. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Lost Acres Vineyard and Enders State Forest are located nearby.
Air conditioning
Parking available
Romantic weekend getaway!
Book a stay at this family-friendly guesthouse in Sandisfield. Enjoy free WiFi, private pools, and a water park. Popular attractions Cookson State Forest and Campbell Falls State Park are located nearby.
Pool
Hot tub
Hudson valley and The Berkshires Cottage
The price is CA $80 per night
CA $80
CA $391 total
includes taxes & fees
22 Dec - 23 Dec
Stay at this guesthouse in Hillsdale. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Catamount Aerial Adventure Park and Art et Industrie are located nearby.
Pet-friendly
Free WiFi
9 Academy
9 Academy St, Salisbury, CT
The price is CA $673 per night
CA $673
CA $774 total
includes taxes & fees
19 Jan - 20 Jan 2025
Stay at this 4-star guesthouse in Salisbury. Enjoy free WiFi, free parking, and a garden. Popular attractions Mount Frissell and Scoville Memorial Library are located nearby.
Parking included
Free WiFi
Renovated Private Guest House by Evergreen Home
Stay at this guesthouse in Great Barrington. Enjoy free WiFi, a garden, and patios. Popular attractions Art et Industrie and Lake Mansfield Park are located nearby.
Pet-friendly
Free WiFi
1805 House Bed and Breakfast
775 Snydertown Road, Craryville, NY
Stay at this 3-star guesthouse in Craryville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Claverack Library and High Falls Trail are located nearby.
Breakfast included
Parking included
Jacob's Tanglewood Ranch
560 Stockbridge Rd, Lee, MA
Stay at this 3-star guesthouse in Lee. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Greenock Country Club and Berkshire Theatre Festival are located nearby.
Pet-friendly
Parking included
Chestnut Lodge
75 Chestnut Street, Lee, MA
Stay at this 3.5-star guesthouse in Lee. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Goose Pond Reservation and Lee Premium Outlets are located nearby.
Hot tub
Parking included
Vanderbilt Lakeside
161 Main St, Philmont, NY
Stay at this 3.5-star guesthouse in Philmont. Enjoy free breakfast, free WiFi, and free parking. Popular attractions High Falls Trail and Hudson Chatham Winery are located nearby.
Breakfast included
Parking included
Don't see what you're looking for?
See all available properties in Great Barrington
View all propertiesLowest 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.
Top trending hotels in Great Barrington
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd, Great Barrington, MA
The price is CA $228 per night from Dec. 24 to Dec. 25
CA $228
CA $255 total
includes taxes & fees
24 Dec - 25 Dec
9.2/10 Wonderful! (673 reviews)
Great Barrington Guest Houses essential information
Accommodation | 10 Guest Houses |
|---|---|
Lowest Price | CA $80 |
Highest Price | CA $673 |
Popular accommodation | The Central Downtown Inn & Suites, The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, Romantic weekend getaway!, Hudson valley and The Berkshires Cottage, 9 Academy , Renovated Private Guest House by Evergreen Home, 1805 House Bed and Breakfast , Jacob's Tanglewood Ranch, Chestnut Lodge, Vanderbilt Lakeside, Guest House Sanctuary by Evergreen Home |