Photo by Elizabeth Massa Peroulakis

Middlefield Holiday Rentals

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Check prices for these dates

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Middlefield

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2149)
"Great place!"
United States
Nicole
The price is HK$576
HK$729 total
includes taxes & fees
29 Nov - 30 Nov
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is HK$1,267
HK$1,416 total
includes taxes & fees
29 Nov - 30 Nov
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,192
HK$1,331 total
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is HK$966
HK$1,080 total
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow
Games room
Pet Friendly Riverfront Home in Great Barrington

Holiday Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is HK$1,575
HK$2,315 total
includes taxes & fees
30 Nov - 1 Dec
Pet Friendly Riverfront Home in Great Barrington
Interior
Peace and quiet on the lake

Holiday Home in Sherwood Forest

9.6 out of 10, Exceptional, (230)
"This property provides direct access to a lovely lake for kayaking and swimming. It is also a terrific location for Berkshire musts such as Jacob's Pillow and Tanglewood. The owner is quickly responsive to questions and directions for check in were easy to follow. The house has strong WiFi for any work days you have while traveling. Highly recommend and look forward to staying there again in the future! "
United States
Leslie K.
Peace and quiet on the lake
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Holiday Home in Lee

8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$2,975
HK$5,738 total
includes taxes & fees
4 Dec - 5 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

Villa in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Holiday Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Holiday Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,134
HK$2,935 total
includes taxes & fees
1 Dec - 2 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Outdoor pool
The Clearing - Quiet - Close To Nature

Cottage in Cummington

10.0 out of 10, Exceptional, (210)
"Very clean home. Grounds and pool are beautiful. My family and I enjoyed a relaxing weekend "
United States
Kimberly P.
The Clearing - Quiet - Close To Nature
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Holiday Home in Hinsdale

9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds
The Creation Station is a cozy place so make yourself at home.

Holiday Home in Easthampton Ma.

10.0 out of 10, Exceptional, (71)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is HK$1,400
HK$2,181 total
includes taxes & fees
1 Dec - 2 Dec
The Creation Station is a cozy place so make yourself at home.
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Holiday Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is HK$2,504
HK$5,637 total
includes taxes & fees
29 Nov - 30 Nov
Comfortable Berkshires retreat on mtn resort, SISO
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Apartment in Lee

9.4 out of 10, Exceptional, (71)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior
Hancock Village Inn Near Jiminy Peak

Holiday Home in Hancock

10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,270
HK$8,146 total
includes taxes & fees
2 Dec - 3 Dec
Hancock Village Inn Near Jiminy Peak
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Holiday Home in Pittsfield

9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Holiday Home in Stockbridge

10.0 out of 10, Exceptional, (134)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Holiday Home in Lenox

9.2 out of 10, Wonderful, (32)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Property grounds
Experience Three Sisters Sanctuary in Goshen, MA

Holiday Home in Goshen

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it."
Steven 4-night trip
Posted 1 day ago
Berkshire Mountain Lodge

Find out more about Middlefield

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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?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Middlefield is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Middlefield?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Skyline Trail. Fox Den Wildlife Management Area and Chester Town Hall 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.