Middlefield, MA Vacation Homes from ￥32,064

A snow-covered forest with a stone bridge in the background.

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Our top choices for Middlefield vacation homes

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

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

Sherwood Forest

Sharon K.

￥57,820 total

includes taxes & fees

Sep 9 - Sep 10

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

￥59,783 total

includes taxes & fees

Sep 9 - Sep 10

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

3. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

￥45,974 total

includes taxes & fees

Sep 13 - Sep 14

A cozy room with two beds, large windows, and a view of a snowy landscape.

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

Easthampton Ma.

Paula

￥42,874 total

includes taxes & fees

Sep 14 - Sep 15

A house with a porch, a garden with pink flowers, and a stone wall along the road.

5. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

￥54,260 total

includes taxes & fees

Sep 9 - Sep 10

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

6. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Anonymous traveler

￥64,980 total

includes taxes & fees

Sep 9 - Sep 10

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

7. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

￥88,963 total

includes taxes & fees

Sep 21 - Sep 22

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

8. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Varun M.

￥32,064 total

includes taxes & fees

Sep 10 - Sep 11

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

9. Riverside Retreat in the Berkshires

Great Barrington

Colin E.

￥48,814 total

includes taxes & fees

Sep 9 - Sep 10

A spacious living room with a dining area, a kitchen, and a large window.

10. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

￥34,548 total

includes taxes & fees

Sep 9 - Sep 10

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

11. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

￥49,245 total

includes taxes & fees

Sep 9 - Sep 10

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Great Barrington

HEATHER G.

￥47,491 total

includes taxes & fees

Sep 15 - Sep 16

A wooden deck with a table and chairs, surrounded by a white railing.

13. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

￥84,734 total

includes taxes & fees

Sep 9 - Sep 10

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

14. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

￥102,451 total

includes taxes & fees

Sep 9 - Sep 10

A white two-story house with a porch, surrounded by trees and a hill.

15. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

￥76,779 total

includes taxes & fees

Sep 10 - Sep 11

16. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Maura L.

￥83,452 total

includes taxes & fees

Sep 9 - Sep 10

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

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

Stockbridge

Anonymous traveler

￥131,894 total

includes taxes & fees

Sep 28 - Sep 29

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

18. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

￥85,963 total

includes taxes & fees

Sep 14 - Sep 15

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

19. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

￥166,872 total

includes taxes & fees

Sep 9 - Sep 10

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

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

Great Barrington

Rebecca K.

￥204,746 total

includes taxes & fees

Sep 9 - Sep 10

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Top Middlefield Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Great place to relax with apartment like qualities. Love the pools! Nice to have the barbeques and fire pit. Great location"

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Very clean room the staff were very pleasant. The breakfast was pretty decent. The only issue we had was parking that didn’t seem to be enough spots for the hotel when we came back from a concert at Tanglewood. Every spot at the hotel was taken. Luckily somebody left otherwise the place was great."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

Find out more about Middlefield

Middlefield Vacation Homes information

Number of reviews	422
Accommodation	324 Vacation Homes
Lowest Price	￥32,064
Highest Price	￥204,746

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlefield vacation homes

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

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

3. Real Estate: Therapy - Lake, Laundry, Love it

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

5. Big farmhouse in the foothills of the Berkshires