Middlefield Holiday Rentals from NZ$184: Search Short-Term Rentals

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Our top choices for Middlefield holiday rentals

1. Berkshire Mountain Lodge

Pittsfield

Karilyn

includes taxes & fees

31 Aug - 1 Sept

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

Sherwood Forest

Sharon K.

includes taxes & fees

9 Sept - 10 Sept

Coffee/tea maker, fridge, microwave, oven

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

Dalton

Megan A.

includes taxes & fees

3 Sept - 4 Sept

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

Sherwood Forest

includes taxes & fees

9 Sept - 10 Sept

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

Sherwood Forest

Frank M.

includes taxes & fees

19 Aug - 20 Aug

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

Hinsdale

Gerard C.

includes taxes & fees

17 Aug - 18 Aug

7. Vacation Village in the Berkshires

Williamstown

peter

includes taxes & fees

31 Aug - 1 Sept

Desk, iron/ironing board, travel cot, WiFi

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

Easthampton Ma.

Paula

includes taxes & fees

31 Aug - 1 Sept

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

New Lebanon

Joanna P.

includes taxes & fees

16 Aug - 17 Aug

10. stylish Berkshires Retreat

Lee

Donna K.

includes taxes & fees

24 Aug - 25 Aug

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

Hancock

Jen B.

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

Hancock

patricia f.

includes taxes & fees

17 Aug - 18 Aug

13. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

includes taxes & fees

23 Aug - 24 Aug

14. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Anonymous traveller

includes taxes & fees

31 Aug - 1 Sept

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

Hancock

John F.

includes taxes & fees

18 Aug - 19 Aug

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

Hancock

Alyne K.

includes taxes & fees

18 Aug - 19 Aug

17. Penthouse Apartment on Park Street

Adams

Margaret C.

includes taxes & fees

16 Aug - 17 Aug

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.

includes taxes & fees

1 Sept - 2 Sept

19. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

includes taxes & fees

19 Aug - 20 Aug

20. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

includes taxes & fees

9 Sept - 10 Sept

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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 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$184 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?

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 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 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.

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Check prices for these dates

Our top choices for Middlefield holiday 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 holiday 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

Quality Inn & Suites Northampton - Amherst

Howard Johnson by Wyndham Lenox

Find out more about Middlefield

Frequently asked questions

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