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Vacation Homes in Middlefield

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
The price is SAR 634
SAR 1,206 total
includes taxes & fees
15 Dec - 16 Dec
Home in the Woods

The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.
10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is SAR 676
SAR 1,040 total
includes taxes & fees
3 Dec - 4 Dec
The Creation Station is a cozy place so make yourself at home.

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is SAR 547
SAR 1,416 total
includes taxes & fees
15 Dec - 16 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is SAR 601
SAR 1,472 total
includes taxes & fees
15 Dec - 16 Dec
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (143)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
United States
Jon O.
The price is SAR 750
SAR 1,364 total
includes taxes & fees
15 Dec - 16 Dec
Big farmhouse in the foothills of the Berkshires

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
The price is SAR 608
SAR 1,018 total
includes taxes & fees
15 Dec - 16 Dec
Home in Great Barrington

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is SAR 507
SAR 1,396 total
includes taxes & fees
3 Dec - 4 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is SAR 1,010
SAR 1,849 total
includes taxes & fees
4 Dec - 5 Dec
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is SAR 507
SAR 910 total
includes taxes & fees
4 Dec - 5 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is SAR 1,069
SAR 1,944 total
includes taxes & fees
4 Dec - 5 Dec
Great Barrington Get Away

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
The price is SAR 991
SAR 2,054 total
includes taxes & fees
3 Dec - 4 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.4 out of 10, Exceptional, (6)
The price is SAR 760
SAR 1,117 total
includes taxes & fees
3 Dec - 4 Dec
Pet Friendly Riverfront Home in Great Barrington

Historic downtown house. Unscented products and sustainability practices.

Northampton
10.0 out of 10, Exceptional, (6)
"We stayed here to move our daughter into Smith, and it was a great property in a beautiful area. Debra was incredibly responsive and helpful and made a stressful time much easier."
United States
Lindsay R.
The price is SAR 1,576
SAR 2,779 total
includes taxes & fees
31 Dec - 1 January 2026
Historic downtown house. Unscented products and sustainability practices.

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
The price is SAR 600
SAR 1,551 total
includes taxes & fees
14 Dec - 15 Dec
Riverbend Berkshire East Basecamp - 3 bedrooms available

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is SAR 2,211
SAR 4,124 total
includes taxes & fees
3 Dec - 4 Dec
Hancock Village Inn Near Jiminy Peak

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington
10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is SAR 2,124
SAR 4,983 total
includes taxes & fees
9 Dec - 10 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is SAR 1,594
SAR 2,992 total
includes taxes & fees
15 Dec - 16 Dec
Spacious 5-bedroom house in charming Lee with WiFi

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is SAR 1,208
SAR 2,749 total
includes taxes & fees
3 Dec - 4 Dec
Comfortable Berkshires retreat on mtn resort, SISO
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.

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Top Middlefield Hotel Reviews