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Middlefield Vacation Rentals

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Check prices for these dates

Tonight
Dec 13 - Dec 14
Tomorrow
Dec 14 - Dec 15
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Middlefield vacation rentals

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2170)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ￥16,166
￥19,764 total
includes taxes & fees
Dec 14 - Dec 15
Vacation Village in the Berkshires
Exterior
Huttopia Berkshires

Camping in Williamstown

Huttopia Berkshires
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 ￥26,503
￥29,604 total
includes taxes & fees
Dec 15 - Dec 16
Huttopia Berkshires
Front of property - evening/night
The Ponds at Foxhollow

Condo resort in Lenox

The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (136)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ￥27,976
￥31,250 total
includes taxes & fees
Dec 15 - Dec 16
Jiminy Peak Mountain Resort
Interior
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington
9.4 out of 10, Exceptional, (6)
The price is ￥31,487
￥46,287 total
includes taxes & fees
Dec 23 - Dec 24
Pet Friendly Riverfront Home in Great Barrington
TV, DVD player, books, video library
Peace and quiet on the lake

Vacation Home in Sherwood Forest

Peace and quiet on the lake
9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Exterior
The Kemble- Built by a US Secretary of State in Lenox

Villa in Lenox

The Kemble- Built by a US Secretary of State 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
Fridge, microwave, oven, stovetop
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Vacation Home in Great Barrington

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
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!
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vacation Home in Stockbridge

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (135)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Vacation Home in Hancock

Comfortable Berkshires retreat on mtn resort, SISO
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is ￥50,068
￥112,685 total
includes taxes & fees
Dec 23 - Dec 24
Comfortable Berkshires retreat on mtn resort, SISO
Interior
Amore Estate - beautiful room with many places to explore and relax in.

Vacation Home in Lenox

Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (33)
"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.
Desk, iron/ironing board, travel crib, WiFi
The Creation Station is a cozy place so make yourself at home.

Vacation Home in Easthampton Ma.

The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (72)
"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 ￥27,988
￥41,684 total
includes taxes & fees
Jan 13 - Jan 14, 2026
The Creation Station is a cozy place so make yourself at home.
Smart TV, fireplace, foosball, books
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Vacation Home in Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (54)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
United States
Danielle R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Property grounds
Experience Three Sisters Sanctuary in Goshen, MA

Vacation Home in Goshen

Experience Three Sisters Sanctuary in Goshen, MA
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
Outdoor dining
Hancock Village Inn Near Jiminy Peak

Vacation Home in Hancock

Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥91,772
￥171,199 total
includes taxes & fees
Dec 15 - Dec 16
Hancock Village Inn Near Jiminy Peak
Property grounds
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Vacation Home in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (150)
"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
Exterior
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Apartment in Lee

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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
Interior
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,717
￥58,268 total
includes taxes & fees
Dec 15 - Dec 16
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
TV, fireplace, offices
Quintessential 6-BR Berkshires Lodge

Vacation Home in Becket

Quintessential 6-BR Berkshires Lodge
9.8 out of 10, Exceptional, (17)
"Great weekend away. Thank you!"
United States
Karen P.
Quintessential 6-BR Berkshires Lodge
Exterior
Cozy cabin in tranquil Canaan NY with WiFi, AC

Cabin in Canaan

Cozy cabin in tranquil Canaan NY with WiFi, AC
Cozy cabin in tranquil Canaan NY with WiFi, AC
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

The Ellery

The Ellery

10/10 Excellent
"Great staff and the room was comfortable and clean. "
John 1-night trip
Posted 2 days ago
The Ellery

Find out more about Middlefield

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Look no further and take a look at our great range of rental properties in Middlefield!

Frequently asked questions

Are there vacation rentals in Middlefield?

Yes, we have vacation rentals near well known sights in Middlefield, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Middlefield?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental near Middlefield comes with WiFi so you can feel at home during your trip.

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 Jacob's Pillow are a couple of places you'll find in the larger area.

What’s a vacation rental in Middlefield like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Middlefield. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.