Middlefield, MA Vacation Homes from AED 764

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

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Our top choices for Middlefield vacation homes

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

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

Sherwood Forest

William C B.

AED 1,120 total

includes taxes & fees

28 Oct - 29 Oct

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.

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

Sherwood Forest

Sharon K.

AED 1,382 total

includes taxes & fees

26 Oct - 27 Oct

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

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

Sherwood Forest

Frank M.

AED 1,445 total

includes taxes & fees

28 Oct - 29 Oct

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

4. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Nancy M.

AED 1,584 total

includes taxes & fees

25 Oct - 26 Oct

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

Dale B.

AED 1,328 total

includes taxes & fees

27 Oct - 28 Oct

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

6. 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.

AED 2,062 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Easthampton Ma.

Paula

AED 1,030 total

includes taxes & fees

3 Nov - 4 Nov

A living room with a sofa, armchairs, a coffee table, and a television.

8. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

AED 2,333 total

includes taxes & fees

26 Oct - 27 Oct

A modern living room with a sofa, armchair, coffee table, and TV.

9. Spacious Central Berkshires Home for Groups

Lee

neil s.

AED 2,205 total

includes taxes & fees

1 Nov - 2 Nov

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

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

New Lebanon

Joanna P.

AED 764 total

includes taxes & fees

27 Oct - 28 Oct

A staircase with a wooden handrail and a white wall with a light switch.

11. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

AED 1,036 total

includes taxes & fees

26 Oct - 27 Oct

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

12. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

AED 1,810 total

includes taxes & fees

25 Oct - 26 Oct

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

13. Ellie’s Overlook, best view in the Berkshires!

Richmond

AED 2,538 total

includes taxes & fees

27 Oct - 28 Oct

14. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

AED 1,988 total

includes taxes & fees

25 Oct - 26 Oct

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

15. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

AED 2,552 total

includes taxes & fees

2 Nov - 3 Nov

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

16. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

AED 827 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Housatonic

Peter S.

AED 1,280 total

includes taxes & fees

25 Oct - 26 Oct

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

18. Home in Great Barrington

Great Barrington

Janet G.

AED 1,314 total

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

19. Mayas Shangrila

Richmond

AED 4,247 total

includes taxes & fees

24 Oct - 25 Oct

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

20. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

AED 2,670 total

includes taxes & fees

25 Oct - 26 Oct

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Top Middlefield Hotel Reviews

Jiminy Peak Mountain Resort

8/10 Good

"The rooms are outdated but they were clean. The hot tubs were down unfortunately which was one reason we booked this resort so that was a bummer but the staff was great and the price was right. The views were gorgeous and it's near hiking trails and a bike trail. Would book it again if they update their rooms and amenities."

Berkshires Untold

10/10 Excellent

"The lobby was absolutely beautiful, aesthetically and structurally! From all the greenery from the plants to the high ceilings, cute seating areas, and nice bar. The outdoor furniture was a plus, especially with the fire pits and the surrounded by the nice view of the berkshires. After an evening out, we came back and played a board game in the lobby and even did a little painting of our own while enjoying some good cocktails…you can definitely create a vibe. The room was clean, and overall it was a great stay if you’re just looking to relax, unwind, and get away for a bit!"

Berkshire Mountain Lodge

10/10 Excellent

"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlefield vacation homes

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

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

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

4. Charming, updated 3 bedroom farmhouse farm stay.