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
Williamstown
8.8 out of 10, Excellent, (2133)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is NZ$208
includes taxes & fees
14 Nov - 15 Nov
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (984)
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
United States
Philip
The price is NZ$285
includes taxes & fees
13 Nov - 14 Nov
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The Ponds at Foxhollow

The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.
10.0 out of 10, Exceptional, (70)
"A very short but a really fun stay. Great location to just relax and get away from it all."
United States
Naseem P.
The price is NZ$399
includes taxes & fees
13 Nov - 14 Nov
The Creation Station is a cozy place so make yourself at home.

Button's Modern Luxury Walkup Downtown Northampton

Northampton
10.0 out of 10, Exceptional, (1)
"This was the best rental apartment I've stayed at and definitely the cleanest. Check-in is easy, the pictures are accurate, the kitchen and bathroom are great, and the location in downtown Northampton is super walkable to cafes, shops, Smith, etc. If I'm ever back anywhere near the area, I will definitely try to stay there again. 10/10"
United States
Meghan C.
The price is NZ$1,074
includes taxes & fees
23 Nov - 24 Nov
Button's Modern Luxury Walkup Downtown Northampton

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (141)
"We enjoyed our stay in this beautiful old farmhouse. Plenty of room for everyone and kitchen and linens were fully stocked."
United States
Nicole K.
The price is NZ$538
includes taxes & fees
17 Nov - 18 Nov
Big farmhouse in the foothills of the Berkshires

Historic downtown house. Unscented products and sustainability practices.

Northampton
10.0 out of 10, Exceptional, (6)
"It’s a beautiful home that worked for our stay as a family "
United States
Camilo W.
The price is NZ$1,076
includes taxes & fees
17 Nov - 18 Nov
Historic downtown house. Unscented products and sustainability practices.

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!"
United States
Jennifer F.
The price is NZ$568
includes taxes & fees
13 Nov - 14 Nov
Home in the Woods

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Very cute! Perfect place for a weekend in the Berkshires"
United States
Melissa P.
The price is NZ$367
includes taxes & fees
13 Nov - 14 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Valley View Post & Beam Villa!

Whately
10.0 out of 10, Exceptional, (8)
"Thanks for a great stay"
United States
Andrea M.
The price is NZ$4,396
includes taxes & fees
11 Dec - 12 Dec
Cozy Valley View Post & Beam Villa!

Penthouse Apartment on Park Street

2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"We had a wonderful relaxing stay in this gorgeous place. The listing is just as described, natural light filled, high ceilings, on the top floor, comfortable bedding, and a thoughtful host. Lea left the A/C on, a bottle of water in the fridge, lots of good coffee, and even some hot cocoa packets for our son. The boba shop right downstairs was awesome and had fun gift items. There is a diner next door and some fantastic restaurants 15-20 minutes away. Very convenient to Mass MOCA and...
United States
Teresa M.
The price is NZ$433
includes taxes & fees
22 Nov - 23 Nov
Penthouse Apartment on Park Street

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"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 NZ$694
includes taxes & fees
13 Nov - 14 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
United States
James F.
The price is NZ$667
includes taxes & fees
17 Nov - 18 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Hancock
10.0 out of 10, Exceptional, (1)
"Great!"
United States
Susan M.
The price is NZ$417
includes taxes & fees
13 Nov - 14 Nov
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock
10.0 out of 10, Exceptional, (4)
"This is my favorite unit of all the units I have stayed in! The pirate stuff was so cool and we could see our kids ski from the inside! The owner is so easy to communicate with. We love having the ability to cook and spread out while we are in the unit. We aaaaargh definitely going to stay here again!"
United States
Stephanie K.
The price is NZ$417
includes taxes & fees
17 Nov - 18 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is NZ$869
includes taxes & fees
14 Nov - 15 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is NZ$429
includes taxes & fees
9 Dec - 10 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
The price is NZ$521
includes taxes & fees
17 Nov - 18 Nov
Home in Great Barrington

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Hancock
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is NZ$533
includes taxes & fees
13 Nov - 14 Nov
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
The price is NZ$731
includes taxes & fees
18 Nov - 19 Nov
Riverbend Berkshire East Basecamp - 3 bedrooms available
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 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 NZ$208 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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: 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 5 bedrooms, as well as a kitchen with a fridge, a stovetop and a coffee maker, so that you can cook with friends or family. You can relax into your holiday with a garden and table football.

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 Glendale Falls 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.