Photo by Elizabeth Massa Peroulakis

Middlefield Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Middlefield Vacation Homes

Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
Cozy apartment located in quiet Williamsburg
Fridge, microwave, oven, stovetop
Cozy apartment located in quiet Williamsburg
9.6 out of 10, Exceptional, (41)
"Property was as advertised. Easy to get in and was exactly what we were looking for. "
The price is CA $202
CA $349 total
includes taxes & fees
Sep 27 - Sep 28
Cozy apartment located in quiet Williamsburg
Historic Farmhouse Near Mountains & Colleges!
Fridge, microwave, stovetop, dishwasher
Historic Farmhouse Near Mountains & Colleges!
Historic Farmhouse Near Mountains & Colleges!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Fridge, microwave, oven, stovetop
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is CA $353
CA $719 total
includes taxes & fees
Sep 29 - Sep 30
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Spectacular views and close to Great Barrington.
Smart TV, fireplace
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (20)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (15)
"This was a beautiful, spacious, and peaceful place for us in our friends to get together. It was centrally located to everything we wanted to do. Amanda was wonderful in her communications and everything was clean and ready for us."
The price is CA $196
CA $477 total
includes taxes & fees
Oct 1 - Oct 2
Near Tanglewood: Historic Summer Retreat
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Property grounds
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
10.0 out of 10, Exceptional, (32)
"Relaxing, quiet, beautiful property. We really enjoyed the views, exploring the grounds and it is a short trip to Stockbridge. We had a wonderful stay. "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Private Home ~ Old World Charm, Modern Conveniences
Fridge, microwave, oven, stovetop
Private Home ~ Old World Charm, Modern Conveniences
10.0 out of 10, Exceptional, (12)
"Very pleased with the property. Just a short drive to many restaurants. "
Private Home ~ Old World Charm, Modern Conveniences
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (213)
"We had a great stay at the carriage house! The property was incredible, we especially loved the variety of trails to explore. Our hosts were very helpful with directions and local recommendations. The house was charming and cozy. Would visit again! "
Berkshire Village Carriage House - Super Private!!
Big farmhouse in the foothills of the Berkshires
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (127)
"We planned a family reunion in the area. The farm house was pet friendly and the perfect location to our family that lived 20 minutes away. Eric was very accommodating. It was quiet and relaxing."
The price is CA $290
CA $520 total
includes taxes & fees
Oct 1 - Oct 2
Big farmhouse in the foothills of the Berkshires
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (141)
"Great place and views. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (34)
"My grown daughter and I stayed here for a two night visit to the Berkshires. It was so nice to have an entire house rather than a hotel room! We received our check in email in plenty of time, the house was clean and furnished with generous amenities such as soaps, shampoos, coffee, etc., the owner was readily available. The house is close to the road, but it really wasn’t a problem…white noise machines and air purifiers made sleeping very comfortable, and there was very little traffic noise....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Golf
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (103)
"We have 2 dogs who travel with us. So renting pet friendly homes is a much better option than a hotel room. The house was clean, comfortable, and the fenced in yard was great for our dogs. Nice big bath towels (my favorite) and a nicely stocked kitchen made staying at this house very enjoyable. An added bonus were two sets of dog-loving neighbors who came out to greet us and say hello to our pups. Thanks Julie for providing a welcoming place to stay for our weekend getaway."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Enjoy comfortable elegance in this secluded grand home located in town
Exterior
Enjoy comfortable elegance in this secluded grand home located in town
10.0 out of 10, Exceptional, (64)
"Perfectly located and lovely appointments make this the place to stay when visiting Lenox, Tanglewood, etc. The home is farm in style but elegantly decorated with thoughtful combinations of old and new. Well laid out floor plan allows groups to host friends and families at the same time. You will be delighted by mornings in the kitchen or evenings in the living spaces. Enjoy! "
Enjoy comfortable elegance in this secluded grand home located in town
Private Access To Laurel Lake, Enjoy Lake Life
Property grounds
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"
Private Access To Laurel Lake, Enjoy Lake Life
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (17)
"At the end of a dead-end street but only two blocks from the center of Stockbridge, this century-old charmer may be the best-kept and best-supplied rental in the Berkshires. We stayed a month(!) and loved it. The location is unbeatable, an easy walk from the Red Lion and within 15 minutes of Tanglewood, The Mount, the Rockwell museum and other attractions. Four local trails begin 100 feet away, including the Ice Glen. A beautiful, productive garden awaits, and the screened front porch may be...
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Your Invited to the Berkshires!
Fridge, microwave, oven, stovetop
Your Invited to the Berkshires!
9.8 out of 10, Exceptional, (29)
"Clean, updated home in the perfect location. Loved the screens in porch! Holly is a wonderful host and her home is a perfect getaway."
Your Invited to the Berkshires!
Comfortable Berkshires retreat on mtn resort, SISO
Pool
Comfortable Berkshires retreat on mtn resort, SISO
9.0 out of 10, Wonderful, (2)
"This property is in a gorgeous setting. It is comfortable to stay in. Everything was in good shape and working. It fit our needs perfectly!"
The price is CA $187
CA $591 total
includes taxes & fees
Oct 1 - Oct 2
Comfortable Berkshires retreat on mtn resort, SISO
Don't see what you're looking for?
See all available properties in Middlefield
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middlefield

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
" We enjoyed our stay at Vacation Villa and the condo was extremely spacious and comfortable. The only complaint is the very soft bed. Upon check- in we were told we were 15 minutes early and had to stand in another line to wait to get a different room that would be ready at 3:45. Since we are gold members of hotel.com we always ask for a room upgrade and the manager seemed annoyed that we even asked for a room upgrade as well as arriving 15 minutes early and the greeting from all of the...
The price is CA $228
CA $263 total
includes taxes & fees
Sep 29 - Sep 30
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (898)
"Was good everything "
The price is CA $191
CA $210 total
includes taxes & fees
Oct 1 - Oct 2
Jiminy Peak Mountain Resort
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (36)
"Communication with property manager was seamless, and above any previous interactions I have ever had. Great place. Well maintained. Clean. Stocked with basic kitchenware and cleaning material. Great Wifi. Tennis Court was such a nice bonus. Would 100% (and will likely) stay here again!"
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.