Middlefield Vacation Rentals from $118: Search Short-Term Rentals

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Our top choices for Middlefield vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Pittsfield

Robert

$125 nightly

Aug 31 - Sep 1

Total with taxes and fees

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Williamstown

Alex

$106 nightly

Sep 28 - Sep 29

Total with taxes and fees

A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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

Hinsdale

Gerard C.

$501 nightly

Sep 1 - Sep 2

Total with taxes and fees

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

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

Sherwood Forest

Sharon K.

$338 nightly

Sep 9 - Sep 10

Total with taxes and fees

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

$355 nightly

Sep 7 - Sep 8

Total with taxes and fees

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

6. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Jamie M.

$392 nightly

Aug 31 - Sep 1

Total with taxes and fees

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

7. 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

A house with a porch, a garden with pink flowers, and a stone wall along the road.

8. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

$316 nightly

Aug 31 - Sep 1

Total with taxes and fees

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

9. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

$781 nightly

Sep 2 - Sep 3

Total with taxes and fees

A cozy room with two beds, large windows, and a view of a snowy landscape.

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

Easthampton Ma.

Paula

$252 nightly

Aug 31 - Sep 1

Total with taxes and fees

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

11. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveler

$766 nightly

Sep 28 - Sep 29

Total with taxes and fees

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

$254 nightly

Sep 13 - Sep 14

Total with taxes and fees

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

13. 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.

$551 nightly

Sep 21 - Sep 22

Total with taxes and fees

A wooden deck with a table and chairs, surrounded by a white railing.

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

$496 nightly

Aug 31 - Sep 1

Total with taxes and fees

15. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Otis

$309 nightly

Sep 7 - Sep 8

Total with taxes and fees

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

16. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

$600 nightly

Aug 31 - Sep 1

Total with taxes and fees

17. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Lenox

$285 nightly

Aug 31 - Sep 1

Total with taxes and fees

A wooden deck with two chairs and a table, overlooking a green landscape with a tree and hills.

18. Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

Noah K.

$837 nightly

Sep 6 - Sep 7

Total with taxes and fees

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

19. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

$269 nightly

Sep 8 - Sep 9

Total with taxes and fees

A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

20. stylish Berkshires Retreat

Lee

$359 nightly

Sep 14 - Sep 15

Total with taxes and fees

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Top Middlefield Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Great for families"

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

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 $118 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 Jacob's Pillow 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.

Room 1

Check prices for these dates

Our top choices for Middlefield vacation rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

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

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

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

6. Charming, updated 3 bedroom farmhouse farm stay.

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

8. Big farmhouse in the foothills of the Berkshires

9. Stylish Mid-century Modern Berkshires Cape

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

11. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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

13. Treetop Hideaway in Tyringham

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

15. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

16. 5BR Berkshire Home Mins To The Mountain

17. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

18. Riverbend Berkshire East Basecamp - 3 bedrooms available

19. Cozy Riverside Berkshires Retreat

20. stylish Berkshires Retreat

Find vacation rentals that suit your style

Top Middlefield Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Jiminy Peak Mountain Resort

Berkshire Mountain Lodge

Berkshires Untold

Quality Inn Great Barrington

Hotel Northampton

Quality Inn Lee - Lenox South

Hotel On North

The Red Lion Inn

Find out more about Middlefield

Frequently asked questions