Search Guest Houses in Great Barrington

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 11 Guest Houses in Great Barrington with updated reviews, rates, and availability.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (269)
"The suite we stayed in was spacious. Maid service is only once weekly, but when we contacted them about getting additional toilet paper, they were very responsive. The queen bed in the bedroom was very comfortable. We were not able to get the TV in the bedroom to work. The sofa queen bed in the living room was all broken down. My husband had to put boards under the mattress to support it enough so he could use the bed. The kitchen was clean and well-stocked."
The Central Downtown Inn & Suites

The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

9.8 out of 10, Exceptional, (84)
"The location was perfect and the loft was very quiet and comfortable. Hope to come back next year."
The price is AED 422
AED 891 total
includes taxes & fees
26 Dec - 27 Dec
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

Romantic weekend getaway!

9.8 out of 10, Exceptional, (52)
"This is by far the best place we have ever stayed. From the beautiful gardens to the hummingbirds drinking nectar from the flowers, from the beautiful suite where the hosts have thought of everything to the great bathroom and calming shower, from the relaxing hot tub to the cooling and revitalizing pool, from the peaceful fire pit to the convenient gas grill, from the comfy couch to the supportive bed, from the ice maker to the fridge and freezer, from the oven to the stove top and even the...
Romantic weekend getaway!

Hudson valley and The Berkshires Cottage

10.0 out of 10, Exceptional, (5)
"The property was beautiful! We did not get to stay as long as we wanted but we will definitely be coming back to this little cottage. It was very clean and decorated well! The host was immediately responsive but we should note that there was absolutely no cellphone service which made communicating with guests a little difficult. "
The price is AED 264
AED 1,080 total
includes taxes & fees
8 Jan - 9 January 2025
Hudson valley and The Berkshires Cottage

9 Academy

4.0 star property
9.6 out of 10, Exceptional, (5)
"The Loft was so beautifully decorated and every detail was perfect. "
The price is AED 1,722
AED 1,980 total
includes taxes & fees
5 Jan - 6 January 2025
9 Academy

Renovated Private Guest House by Evergreen Home

10.0 out of 10, Exceptional, (9)
"Great stay. Cute spot!"
Renovated Private Guest House by Evergreen Home

1805 House Bed and Breakfast

3.0 star property
9.8 out of 10, Exceptional, (38)
"My partner and I thoroughly enjoyed our two nights at the 1805 House B&B. The four-poster king-sized bed was very comfortable, the large tub in the bathroom was a delight, and breakfast was delivered to our room each morning. The hosts made check in and check out very easy. We were in the area for a jazz festival and to visit a friend. This was a lovely country stay for the weekend. "
1805 House Bed and Breakfast

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge

Vanderbilt Lakeside

3.5 star property
9.4 out of 10, Exceptional, (26)
"We loved our stay at the Vanderbilt Lakeside! The house is so stylish and we had a wonderful dinner at the restaurant. Would definitely stay again!"
Vanderbilt Lakeside

Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home
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.
Don't see what you're looking for?
See all available properties in Great Barrington
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Great Barrington

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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.