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Search Middlefield Cottage Rentals from CA $207

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Aug 15 - Aug 17
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Middlefield Cottages

Perfect Vacation Get Away - Historical New Marlborough
Enjoy al fresco dining and socializing in this serene outdoor patio area surrounded by lush greenery and trees.

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"Lovely place!"
The price is CA $207
CA $381 total
includes taxes & fees
Sep 3 - Sep 4
Perfect Vacation Get Away - Historical New Marlborough
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Surrounded by tall trees, this cozy cabin offers a peaceful retreat in a natural setting.

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (39)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
The Clearing - Quiet - Close To Nature
Surrounded by a serene lawn and a tranquil pond, this peaceful setting offers a serene escape.

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (192)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
Charming historic cottage on scenic road to Mt. Greylock
Stroll through the serene garden, surrounded by vibrant flowers and lush greenery, with a charming house in the background.

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (111)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
East Otis Vacation Rental w/ Private Deck & BBQ!
Relax in this inviting room with a plush bed, sofa, and TV, offering stunning views of Lake.

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (10)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Lake Views & Dock Access - Pittsfield Cottage!
Sit by the lake and enjoy a serene moment with a cup on the dock.

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (4)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
Lake Views & Dock Access - Pittsfield Cottage!
Massachusetts Vacation Rental w/ Deck
House (3 Bedrooms) | Interior

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Private Island - Largest Fresh Water Reservoir in Mass....
Relax in this cabin's open-plan living area with a fireplace, scenic lake views, and comfortable seating.

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Westfield Vacation Rental w/ Porch, Pets Welcome!
Stylish single-story home with a gabled roof and a cozy front porch.

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Beachwood Cottage
Cozy interior with a brick fireplace, wooden ceiling, and a panelled wall.

Beachwood Cottage

10.0 out of 10, Exceptional, (4)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Entire cottage in Berkshire Villiage
Relax in this inviting living room with a plush sofa, a statement rug, and a tall floor lamp.

Entire cottage in Berkshire Villiage

3.0 star property
9.6 out of 10, Exceptional, (4)
"Elise's place is like one of those perfect romantic getaways. It's very pretty, cozy, and comfortable, with a well-appointed kitchen, and excellent wifi. Perfect for couples, and for writers seeking lovely solitude and inspiration. Could also work for families, because of the pull-out bed and two bathrooms. Highly recommended. "
Entire cottage in Berkshire Villiage
Historic Huntington Home - Walk to Westfield River
Kitchen features a large window, refrigerator, stove, and dishwasher, with a ceiling fan for ventilation.

Historic Huntington Home - Walk to Westfield River

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."
Historic Huntington Home - Walk to Westfield River
Quiet rustic cottage with shared lake access
Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, stove, and refrigerator.

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (109)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Relax in a peaceful room with large windows overlooking the surrounding trees, a perfect spot for socializing and taking in the views.

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (12)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Grandparent’s Cottage 250 steps to the lake
Sun loungers, beach towels

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
Charlemont Retreat on Chickley River w/ EV Charger
Enjoy the serene surroundings and well-maintained deck adjacent to this house.

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Relax in the inviting porch area with Adirondack chairs and a cozy table.

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (5)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Berkshires farm, 30+ guests, 50 acres
Situated on a grassy area, this charming home features a traditional two-story design with a prominent porch and a small attached structure.

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is CA $1,672
CA $2,699 total
includes taxes & fees
Sep 2 - Sep 3
Berkshires farm, 30+ guests, 50 acres
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
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

Hotel Northampton

Hotel Northampton

10/10 Excellent
"I really enjoyed staying at this hotel. While some may comment that the bathrooms are older they are still impeccable and in perfect working order and I liked the space very much. The staff were wonderful."
Lydia 2-night trip
Posted 8 hours ago
Hotel Northampton