Middlefield, MA Cottage Rentals from $2,339

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

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Our top choices for Middlefield cottages

1. Berkshires farm, 30+ guests, 50 acres

New Lebanon

$2,305 nightly

Sep 30 - Oct 1

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Top Middlefield Hotel Reviews

Hotel Northampton

10/10 Excellent

"Older hotel. Great location. Nice bar. Nice staff. Zero complaints for a quick overnight."

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

Berkshires Untold

10/10 Excellent

"The entry , bar, and dining room along with the outside patio was beautifully done. It made you happy to be there as it was so welcoming. Ample parking space, great amenities, and comfy quiet room made our stay great. The only thing missing was a floor lamp in our room so we couldn’t read at night as the small lamps were dim."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

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Middlefield Cottages information

Number of reviews
Accommodation	91 Cottages
Lowest Price	$2,339
Highest Price	$2,339

Frequently asked questions

Why book your cottage in Middlefield with Expedia?

Expedia has some superb cottages in Middlefield, so start packing for a memorable stay on nature's doorstep. If you have a budget in mind, select how much you want to spend and your preferred property star rating. Or take advantage of our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect place whatever your trip looks like.

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What is there to do in Middlefield near my cottage?

The most practical travel accessory is a well-planned schedule. Skyline Trail is a top place to kick off your adventures in Middlefield.

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Becket Vacation Rentals

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Our top choices for Middlefield cottages

1. Berkshires farm, 30+ guests, 50 acres

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Top Middlefield Hotel Reviews

Hotel Northampton

Quality Inn Great Barrington

The Red Lion Inn

Berkshire Mountain Lodge

Berkshires Untold

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

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Jiminy Peak Mountain Resort

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Middlefield Cottages information

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Our top choices for Middlefield cottages

1. Berkshires farm, 30+ guests, 50 acres

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Top Middlefield Hotel Reviews

Hotel Northampton

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Middlefield Cottages information

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