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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Middlefield holiday homes

1 bedroom, desk, iron/ironing board, travel cot

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

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (75 reviews)
"An amazing location with the most friendly host! My mom, dog and i absolutely enjoyed this spot. Perfect for a fall get away and would stay again."
United States
Kelly Z.
The price is £205
includes taxes & fees
19 May - 20 May
The Creation Station is a cozy place so make yourself at home.
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is £283
includes taxes & fees
18 May - 19 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is £259
includes taxes & fees
18 May - 19 May
Big farmhouse in the foothills of the Berkshires
Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is £306
includes taxes & fees
1 Jun - 2 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is £291
includes taxes & fees
18 May - 19 May
Near Tanglewood: Historic Summer Retreat
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is £298
includes taxes & fees
18 May - 19 May
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is £235
includes taxes & fees
19 May - 20 May
Cozy Riverside Berkshires Retreat
Exterior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is £234
includes taxes & fees
20 May - 21 May
Real Estate: Therapy - Lake, Laundry, Love it
Fridge, microwave, oven, stovetop

Historic downtown house. Unscented products and sustainability practices.

Historic downtown house. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (7 reviews)
"The house was very comfortable and we enjoyed our visit very much "
United States
Debbie L.
The price is £560
includes taxes & fees
18 May - 19 May
Historic downtown house. Unscented products and sustainability practices.
Outdoor dining

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

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is £372
includes taxes & fees
19 May - 20 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is £400
includes taxes & fees
18 May - 19 May
Comfortable Berkshires retreat on mtn resort, SISO
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is £581
includes taxes & fees
18 May - 19 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is £453
includes taxes & fees
18 May - 19 May
5BR Berkshire Home Mins To The Mountain
TV, fireplace, printers

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"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 £996
includes taxes & fees
18 May - 19 May
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is £428
includes taxes & fees
18 May - 19 May
Treetop Hideaway in Tyringham
Dining

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"It was a lovely four day stay. There was everything we needed in the large kitchen. The livingroom was comfortable and spacious. We especially enjoyed the back deck and the view of the mountains. If we return to the area, we'll definitely stay here again."
United States
Marianne B.
The price is £351
includes taxes & fees
22 May - 23 May
Riverbend Berkshire East Basecamp - 3 bedrooms available
Private kitchen

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is £310
includes taxes & fees
18 May - 19 May
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is £395
includes taxes & fees
18 May - 19 May
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is £643
includes taxes & fees
25 May - 26 May
Spacious 5-bedroom house in charming Lee with WiFi
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is £814
includes taxes & fees
19 May - 20 May
Hancock Village Inn Near Jiminy Peak
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The staff is wonderful!"
Leslie 1-night trip
Posted 5 hours ago
The Red Lion Inn

Find out more about Middlefield

Middlefield Holiday Homes information

Number of reviews
388
Accommodation
308 Holiday Homes
Lowest Price
£205
Highest Price
£996