Middlefield Vacation Homes

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

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Our top choices for Middlefield holiday 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.

HK$2,381 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.

HK$2,948 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.

HK$3,083 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.

HK$3,380 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.

HK$2,833 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

Sarah B.

HK$4,399 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

HK$2,197 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.

HK$4,985 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.

HK$4,705 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.

HK$1,630 total

includes taxes & fees

27 Oct - 28 Oct

A dining area with a wooden table and chairs, a ceiling fan, and a view of the outdoors through windows.

11. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

HK$2,210 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.

HK$3,888 total

includes taxes & fees

26 Oct - 27 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

HK$5,416 total

includes taxes & fees

2 Nov - 3 Nov

14. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

HK$4,278 total

includes taxes & fees

27 Oct - 28 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.

HK$5,445 total

includes taxes & fees

11 Nov - 12 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.

HK$1,765 total

includes taxes & fees

15 Nov - 16 Nov

A dining area with a wooden table, black chairs, and a vase with green plants.

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

Housatonic

Peter S.

HK$2,731 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.

HK$2,805 total

includes taxes & fees

29 Oct - 30 Oct

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

19. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

HK$5,697 total

includes taxes & fees

25 Oct - 26 Oct

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Top Middlefield Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Clean large room. Nice bathroom Walling distance to downtown and many restaurant options."

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."

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