Middlefield Vacation Rentals from $139: Search Short-Term Rentals

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Our top choices for Middlefield vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Karilyn

$125 nightly

Aug 31 - Sep 1

Total with taxes and fees

2. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

$366 nightly

Sep 9 - Sep 10

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

3. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Megan A.

$293 nightly

Aug 31 - Sep 1

Total with taxes and fees

4. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

$313 nightly

Sep 9 - Sep 10

Total with taxes and fees

5. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

$368 nightly

Aug 19 - Aug 20

Total with taxes and fees

6. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Gerard C.

$493 nightly

Aug 19 - Aug 20

Total with taxes and fees

7. Vacation Village in the Berkshires

Williamstown

peter

$128 nightly

Aug 31 - Sep 1

Total with taxes and fees

Desk, iron/ironing board, travel crib, WiFi

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

Easthampton Ma.

Paula

$244 nightly

Aug 31 - Sep 1

Total with taxes and fees

9. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

$213 nightly

Aug 16 - Aug 17

Total with taxes and fees

10. stylish Berkshires Retreat

Lee

Donna K.

$373 nightly

Sep 9 - Sep 10

Total with taxes and fees

11. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Jen B.

$244 nightly

Aug 19 - Aug 20

Total with taxes and fees

12. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

$247 nightly

Aug 16 - Aug 17

Total with taxes and fees

13. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

$316 nightly

Aug 23 - Aug 24

Total with taxes and fees

14. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Anonymous traveler

$392 nightly

Aug 31 - Sep 1

Total with taxes and fees

15. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Hancock

John F.

$240 nightly

Aug 18 - Aug 19

Total with taxes and fees

16. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Hancock

Alyne K.

$240 nightly

Aug 18 - Aug 19

Total with taxes and fees

17. Penthouse Apartment on Park Street

Adams

Margaret C.

$252 nightly

Aug 16 - Aug 17

Total with taxes and fees

18. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

$606 nightly

Sep 2 - Sep 3

Total with taxes and fees

19. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

$269 nightly

Sep 7 - Sep 8

Total with taxes and fees

20. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

$241 nightly

Sep 9 - Sep 10

Total with taxes and fees

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Top Middlefield Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"A nice place to stay in the Berkshires."

The Whitlock

10/10 Excellent

"We visited on a Tanglewood concert night in August. Check-in process was super easy and staff was reachable almost immediately via text. Very clean, updated and well-appointed room. Bar area was quiet but someone was always accessible to get us ice or an adult beverage. Complimentary water & coffee. Lovely outdoor courtyard where we enjoyed the fire pit post-concert. Great location… walkable to all shops and restaurants! Would highly recommend and will definitely stay here again!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."

Berkshires Untold

8/10 Good

"Lovely man at check in for our overnight ( to see Hugh Jackman at 7 pm at Tanglewood lucky us!👍 Checked that food would be available in their bar upon our trying as has driven 2+ hrs assured yes until just before 10 pm closing. Called once on way back at 9:10 for 10 min drive to dbl check as hungry. Woman said no, they stopping serving at 9... luckily she rec one place nearby which was still open for food til midnight! Wow in Lenox! Very packed loud and fun w locals & Jackman fans..got wines, friendly bartenders, ordered yummy plates of tacos , sandwich and ended eve on a great note . Go to OMBRA if hungry after 9! Small complaint this am also.. we ordered a bagel & a berry salad from the hotel's brkfst menu to go as needed to drive back home mid am.. Opened it and about 1/2 cup of mixed berries ..for $11.00... Think the bagel was 8. Oh well -worth the splurge to see Hugh 💕and only 10 min drive to Tanglewood & downtown Lenox! Hotel not walkable to anything but ez parking & very cute interior & bar & seating areas!"

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 $139 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near Middlefield is located near skiing and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 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.

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Upfront pricing

Check prices for these dates

Our top choices for Middlefield vacation rentals

1. Berkshire Mountain Lodge

2. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

3. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

4. Real Estate: Therapy - Lake, Laundry, Love it

5. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

6. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

7. Vacation Village in the Berkshires

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

9. NEW RENO - Chalet-style farm loft near Tanglewood

10. stylish Berkshires Retreat

11. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

12. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

13. Big farmhouse in the foothills of the Berkshires

14. Charming, updated 3 bedroom farmhouse farm stay.

15. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

16. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

17. Penthouse Apartment on Park Street

18. Treetop Hideaway in Tyringham

19. Cozy Riverside Berkshires Retreat

20. 1800s Carriage house in Berkshires / Hudson Valley

Find vacation rentals that suit your style

Top Middlefield Hotel Reviews

Berkshire Mountain Lodge

The Yankee Inn

The Whitlock

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Great Barrington

Berkshires Untold

Jiminy Peak Mountain Resort

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Quality Inn & Suites Northampton - Amherst

Find out more about Middlefield

Frequently asked questions

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