Middlefield Vacation Rentals from $123: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Middlefield?

Experience Three Sisters Sanctuary in Goshen, MA : This vacation home rental near Middlefield is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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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

Joel

$110 nightly

Nov 18 - Nov 19

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

Adrianne

$126 nightly

Nov 18 - Nov 19

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.

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

Sherwood Forest

Sharon K.

$336 nightly

Oct 26 - Oct 27

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.

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

Sherwood Forest

William C B.

$276 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

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

Hinsdale

Kyle R.

$439 nightly

Oct 19 - Oct 20

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

Nancy M.

$402 nightly

Oct 25 - Oct 26

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

Allie T.

$322 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

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

Sherwood Forest

Frank M.

$352 nightly

Oct 28 - Oct 29

Total with taxes and fees

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

9. Cozy Cottage-Sunset On The Lake

Otis

Michael S.

$515 nightly

Oct 19 - Oct 20

Total with taxes and fees

A living room with a sofa, armchairs, a coffee table, and a television.

10. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

$569 nightly

Oct 19 - Oct 20

Total with taxes and fees

A modern living room with a sofa, armchair, coffee table, and TV.

11. Spacious Central Berkshires Home for Groups

Lee

neil s.

$538 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

12. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

$342 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

13. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

$441 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

14. 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.

$530 nightly

Nov 16 - Nov 17

Total with taxes and fees

A snow-covered outdoor area with a fire pit, tables, and chairs.

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

Hancock

Maura D.

$205 nightly

Oct 20 - Oct 21

Total with taxes and fees

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

16. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

$578 nightly

Oct 20 - Oct 21

Total with taxes and fees

A staircase with a wooden handrail and a white wall with a light switch.

17. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

$253 nightly

Oct 26 - Oct 27

Total with taxes and fees

A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

18. Penthouse Apartment on Park Street

Adams

Margaret C.

$252 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

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

Easthampton Ma.

Paula

$248 nightly

Nov 3 - Nov 4

Total with taxes and fees

A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

20. Cozy Camper tucked into the woods

Sandisfield

"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...

hannah w.

$178 nightly

Oct 20 - Oct 21

Total with taxes and fees

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Top Middlefield Hotel Reviews

River Valley Inn

10/10 Excellent

"Had a very pleasant stay here! Staff is very warm and helpful."

The Yankee Inn

8/10 Good

"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"

Berkshire Mountain Lodge

8/10 Good

"This really is a great place and I will give it five stars, except the Wi-Fi is really crappy. We were on the fifth floor, but five MB/s is unacceptable in this day and age. The room was beautiful, and the kitchen was fabulous. One more nit is that they didn't make up the sofa bed. Most places make the sofa bed and fold it with the sheets and blanket inside. I found that sound late at night, and was not happy, but I understand. Still except for the WiFi this is 5 stars."

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 $123 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?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental near Middlefield is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals will I find in Middlefield?

Expedia has 3 vacation rentals for your stay in Middlefield.

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.

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Check prices for these dates

Our top choices for Middlefield vacation rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

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

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

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

6. Charming, updated 3 bedroom farmhouse farm stay.

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

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

9. Cozy Cottage-Sunset On The Lake

10. Sun Filled Lenox Retreat - Minutes to Tanglewood!

11. Spacious Central Berkshires Home for Groups

12. Big farmhouse in the foothills of the Berkshires

13. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

14. Treetop Hideaway in Tyringham

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

16. Secluded Family Home in Serene Stockbridge Woods

17. Leaf-Peeper Paradise in the Berkshires

18. Penthouse Apartment on Park Street

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

20. Cozy Camper tucked into the woods

Find vacation rentals that suit your style

Top Middlefield Hotel Reviews

River Valley Inn

Quality Inn Great Barrington

Quality Inn & Suites Northampton - Amherst

The Yankee Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

Berkshire Mountain Lodge

The Ellery

Hotel Northampton

Berkshires Untold

Find out more about Middlefield

Frequently asked questions

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