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Middlefield Vacation Rentals

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Our top choices for Middlefield vacation rentals

10.0 out of 10, Exceptional, (72 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.
$203 nightly
The price is $227
Jan 11 - Jan 12
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
3.0 star property
8.8 out of 10, Excellent, (2,204 reviews)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Jan 11 - Jan 12
Total with taxes and fees
Vacation Village in the Berkshires
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
$677 nightly
The price is $756
Jan 12 - Jan 13
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
$306 nightly
The price is $323
Jan 10 - Jan 11
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
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.
$337 nightly
The price is $376
Jan 12 - Jan 13
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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.
$353 nightly
The price is $395
Jan 12 - Jan 13
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.4 out of 10, Exceptional, (40 reviews)
"Patrick was super nice and his farmers market/ cafe is great. Got to cut my own flowers from his field for free! I would definitely stay there again if in the area."
United States
Patricia A.
Charming Apt in 18th c Berkshire Farmhouse
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.
$376 nightly
The price is $420
Jan 11 - Jan 12
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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
$540 nightly
The price is $603
Jan 11 - Jan 12
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
10.0 out of 10, Exceptional, (1 review)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
$378 nightly
The price is $422
Jan 12 - Jan 13
Total with taxes and fees
Riverbend Berkshire East Basecamp - 3 bedrooms available

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (988 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$208 nightly
The price is $233
Jan 12 - Jan 13
Total with taxes and fees
Jiminy Peak Mountain Resort
2.0 star property
9.6 out of 10, Exceptional, (13 reviews)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$219 nightly
The price is $245
Jan 10 - Jan 11
Total with taxes and fees
Penthouse Apartment on Park Street

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
$166 nightly
The price is $186
Jan 11 - Jan 12
Total with taxes and fees
Huttopia Berkshires

Vacation 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.
$227 nightly
The price is $254
Feb 9 - Feb 10
Total with taxes and fees
Home in Great Barrington
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.
$246 nightly
The price is $275
Jan 11 - Jan 12
Total with taxes and fees
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
10.0 out of 10, Exceptional, (8 reviews)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
$247 nightly
The price is $276
Jan 11 - Jan 12
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
$412 nightly
The price is $460
Jan 11 - Jan 12
Total with taxes and fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
$247 nightly
The price is $276
Jan 11 - Jan 12
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
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.
$440 nightly
The price is $492
Jan 11 - Jan 12
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
8.8 out of 10, Excellent, (20 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
$352 nightly
The price is $394
Feb 9 - Feb 10
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlefield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlefield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middlefield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlefield rentals

At Expedia, we put the best Middlefield vacation 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 vacation.

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 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental near Middlefield offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a 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 Chesterfield Gorge 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.