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Compare 255 Vacation Homes in Middlefield with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is AED 551
AED 837 total
includes taxes & fees
14 Jan - 15 Jan
Berkshire Village Carriage House - Super Private!!

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (202)
"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"
Peace and quiet on the lake

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (21)
"Our family had a wonderful stay. The house was very comfortable and the owner was very responsive. The sound of the river right outside was delightful! The bathrooms are very nicely updated - a nice perk when staying in an older home. "
Charlemont Retreat on Chickley River w/ EV Charger

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (39)
"We had a great stay. The house was well furnished, with plenty of space for us, our children, and my parents. There was a nice dining room and a decent kitchen. Our kids loved the arcade machine and air hockey table, and it was a convenient location. The host was very responsive and friendly. The checkout rules were a bit stringent, and it had the quirks of an older house, but overall we loved the place and would highly recommend it to others. "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (84)
"Very nice place, clean, great communication. "
Plainfield House in a 10,000 acre state forest and private pond

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (9)
"The house was clean and beautiful. We had a few questions and the property manager was very responsible and helpful. I would 1000% stay here again and would recommend to anyone. "
Quintessential 6-BR Berkshires Lodge

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (129)
"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."
The price is AED 790
AED 1,402 total
includes taxes & fees
13 Jan - 14 Jan
Big farmhouse in the foothills of the Berkshires

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (14)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (149)
"The location is beautiful and there are lots of places to visit in the area. The house is nice; great view of Otis Reservoir. It took us a while to figure out the multiple thermostats, but it was a good Christmas house. The owner was nice enough to allow us to have a Christmas tree, and had someone make an extra trash pick up for us after Christmas.The one thing we were disappointed in was the cleanliness. Shower curtains were moldy, some of the dishes weren't very clean, expired condiments...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Amore Estate - beautiful room with many places to explore and relax in.

9.2 out of 10, Wonderful, (20)
"We had a lovely time on our family holiday trip. Andrea was great- easy to get ahold of, clear communication. The house and neighborhood are so charming. Everything was well stocked, comfortable, and even decorated for the holdiays! We’d love to stay again!"
Amore Estate - beautiful room with many places to explore and relax in.

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (18)
"Amanda is a very responsive and accommodating host. The house was comfortable and perfect for our girls weekend with plenty of space for us to relax and feel at home. "
The price is AED 422
AED 1,169 total
includes taxes & fees
13 Jan - 14 Jan
Near Tanglewood: Historic Summer Retreat

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (86)
"Simply fantastic!"
Hearts Desire is a furnished whole house in a small, colorful garden center.

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (93)
"Property was beautiful and walkable to town. House is old but very nice. Large enough to accommodate 9 women! Loved sitting outside enjoying perfect weather! All in all had a wonderful experience!"
A Grand property in Historic Stockbridge

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (18)
"As advertised, easy check-in, good location"
Massachusetts Vacation Rental w/ Deck

Dancing Horse Lodge

9.4 out of 10, Exceptional, (38)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

Stockbridge Home: Walk to Town Beach!

9.8 out of 10, Exceptional, (10)
"A friend and I stayed at this property when the Trauma Healing Immersion event at Kripalu had them fully booked. As someone who normally stays at Kripalu when attended events I was hesitant to find property close enough to create an experience that was still as full of peace and solace as I am used to. This property was just what the dr. ordered. I love the bathroom remodel! It was quiet and peaceful which was just what we needed after a long day of lecture and experiential training. "
Stockbridge Home: Walk to Town Beach!

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (21)
"Very enjoyable time. Nice location. Kari & Glenn made everything easy ."
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
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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Other property types in Middlefield

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1754)
"We always come back to Vacation Village! We love the space and area."
The price is AED 689
AED 792 total
includes taxes & fees
14 Jan - 15 Jan
Vacation Village in the Berkshires

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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.