Photo by Elizabeth Massa Peroulakis

Holiday Rentals in Middlefield

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Our top choices for Middlefield holiday rentals

10.0 out of 10, Exceptional, (73 reviews)
"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 €236
includes taxes & fees
9 Feb - 10 Feb
The Creation Station is a cozy place so make yourself at home.
3.0 star property
8.8 out of 10, Excellent, (2,209 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is €109
includes taxes & fees
19 Jan - 20 Jan
Vacation Village in the Berkshires
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is €665
includes taxes & fees
19 Jan - 20 Jan
Cozy Valley View Post & Beam Villa!
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €322
includes taxes & fees
21 Jan - 22 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is €320
includes taxes & fees
18 Jan - 19 Jan
Big farmhouse in the foothills of the Berkshires
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is €340
includes taxes & fees
21 Jan - 22 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (67 reviews)
"What a quaint and comfy place!"
United States
Lori A.
The price is €183
includes taxes & fees
20 Jan - 21 Jan
Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
The price is €415
includes taxes & fees
16 Jan - 17 Jan
Little Longbow Lakefront Chalet
9.6 out of 10, Exceptional, (9 reviews)
"Great place for a large family get together, convenient to downtown Westfield. Nice big fenced yard, good for dogs. "
United States
Harry M.
Owl`s Nest - Cozy Westfield Home w/ Fire Pit

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is €220
includes taxes & fees
26 Jan - 27 Jan
Home in Great Barrington
9.8 out of 10, Exceptional, (35 reviews)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is €419
includes taxes & fees
21 Jan - 22 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is €210
includes taxes & fees
21 Jan - 22 Jan
Jiminy Peak Mountain Resort
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is €530
includes taxes & fees
18 Jan - 19 Jan
Button's Modern Luxury Walkup Downtown Northampton

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.2 out of 10, Wonderful, (25 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is €312
includes taxes & fees
25 Jan - 26 Jan
Near Tanglewood: Historic Summer Retreat
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is €243
includes taxes & fees
19 Jan - 20 Jan
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is €371
includes taxes & fees
26 Jan - 27 Jan
Riverbend Berkshire East Basecamp - 3 bedrooms available

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is €183
includes taxes & fees
19 Jan - 20 Jan
Huttopia Berkshires
2.0 star property
9.6 out of 10, Exceptional, (14 reviews)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is €216
includes taxes & fees
16 Jan - 17 Jan
Penthouse Apartment on Park Street
2.0 star property
The price is €573
includes taxes & fees
20 Jan - 21 Jan
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
10.0 out of 10, Exceptional, (8 reviews)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is €243
includes taxes & fees
19 Jan - 20 Jan
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
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

Find out more about Middlefield

Everything you need to know about Middlefield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlefield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlefield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlefield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlefield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlefield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlefield holiday rentals we have selected for you start as low as €109 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlefield rentals

At Expedia, we put the best Middlefield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlefield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlefield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlefield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Middlefield offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.