Middlefield Holiday Rentals

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Our top choices for Middlefield holiday rentals

10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is AU$1,041
includes taxes & fees
10 Mar - 11 Mar
Cozy Valley View Post & Beam Villa!
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 AU$394
includes taxes & fees
9 Mar - 10 Mar
The Creation Station is a cozy place so make yourself at home.
3.0 star property
8.8 out of 10, Excellent, (2,276 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is AU$179
includes taxes & fees
31 Mar - 1 Apr
Vacation Village in the Berkshires

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 AU$234
includes taxes & fees
2 Apr - 3 Apr
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 AU$853
includes taxes & fees
8 Mar - 9 Mar
Button's Modern Luxury Walkup Downtown Northampton
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is AU$903
includes taxes & fees
5 Mar - 6 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is AU$764
includes taxes & fees
1 Apr - 2 Apr
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
The price is AU$434
includes taxes & fees
9 Mar - 10 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is AU$483
includes taxes & fees
5 Mar - 6 Mar
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (2 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AU$899
includes taxes & fees
8 Mar - 9 Mar
Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, attentive host. Location is as peaceful as can be. "
United States
Rick M.
The price is AU$892
includes taxes & fees
11 Mar - 12 Mar
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AU$612
includes taxes & fees
5 Mar - 6 Mar
Riverbend Berkshire East Basecamp - 3 bedrooms available
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AU$679
includes taxes & fees
5 Mar - 6 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is AU$543
includes taxes & fees
12 Mar - 13 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Holiday Home in Monterey

Treetop Hideaway in Tyringham
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$764
includes taxes & fees
11 Mar - 12 Mar
Treetop Hideaway in Tyringham

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is AU$378
includes taxes & fees
10 Mar - 11 Mar
Home in Great Barrington
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,216
includes taxes & fees
5 Mar - 6 Mar
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
10.0 out of 10, Exceptional, (3 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AU$1,834
includes taxes & fees
8 Mar - 9 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is AU$356
includes taxes & fees
10 Mar - 11 Mar
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Camping in Williamstown

Huttopia Berkshires
1.0 star property
9.4 out of 10, Exceptional, (9 reviews)
"Healthy food too!"
United States
GEORGINA
The price is AU$265
includes taxes & fees
16 Mar - 17 Mar
Huttopia Berkshires
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, 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 favourite 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 depend 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 AU$179 per night. Entering your travel dates in the search wizard might find you 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Middlefield is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease 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 garden and a selection of games.

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 Jacob's Pillow 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.