Photo by Elizabeth Massa Peroulakis

Middlefield Holiday Rentals

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Holiday Rentals in Middlefield

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is AU$300
includes taxes & fees
1 Dec - 2 Dec
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AU$251
includes taxes & fees
26 Nov - 27 Nov
Jiminy Peak Mountain Resort

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AU$344
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is AU$399
includes taxes & fees
24 Nov - 25 Nov
Cozy apartment located in quiet Williamsburg

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (9)
"Enjoyed the foliage and some nice hikes. House was comfortable and clean. Owner was responsive and helpful. We arrived at night and had trouble locating the property when our gps failed. Owner was helpful guiding us to the house. I suggest arriving in the light of day. "
Berkshires Cabin 2 Mi to Appalachian Trail!

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (125)
"We stayed two days but were mostly for sleep and sightseeing/visits. Certainly fit the bill for our needs. Would recommend to friends "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Berkshire Lake access

10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

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

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

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (25)
"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is AU$556
includes taxes & fees
20 Dec - 21 Dec
Big farmhouse in the foothills of the Berkshires

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough
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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Other types of properties in Middlefield you may be interested in

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1020)
"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. The dinner was delicious. Plenty of seats but gave us a table facing wall (but near window) —why not more in middle of room area with more interesting view! And same table for breakfast and...
The price is AU$326
includes taxes & fees
1 Dec - 2 Dec
The Red Lion Inn

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (442)
"Looking forward to our weekend here. So far this establishment is fabulous! "
The price is AU$205
includes taxes & fees
25 Nov - 26 Nov
Life House Berkshires

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very good, (682)
"We stayed for two weeks and couldn’t have been happier with the service. Such nice people, and so understanding. Six stars if I could!"
The price is AU$163
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Are there holiday rentals in Middlefield?

Yes, there are holiday rentals close to the most popular sights in Middlefield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middlefield has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Middlefield is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals will I find in Middlefield?

Expedia has 3 holiday rentals for your stay in Middlefield.

What’s there to see and do in Middlefield?

While exploring the area, visit family-friendly sights like Berkshire Scenic Railway Museum, or get outside and enjoy nature at Skyline Trail. Fox Den Wildlife Management Area and October Mountain State Forest are a couple of places you'll find in the wider area.

What’s a holiday rental in Middlefield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlefield. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.