A snow-covered forest with a stone bridge in the background.

Middlefield Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middlefield vacation rentals

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

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,161 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
$109 nightly
The price is $121
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
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.

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$336 nightly
The price is $375
Sep 30 - Oct 1
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,686 reviews)
"Love this place for a weekend getaway."
United States
Jacob
$122 nightly
The price is $136
Sep 30 - Oct 1
Total with taxes and fees
Vacation Village in the Berkshires
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (17 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$352 nightly
The price is $393
Sep 30 - Oct 1
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
$382 nightly
The price is $427
Sep 30 - Oct 1
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

6. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (53 reviews)
"Great lake house in the beautiful Berkshires. House looked just like the online pics. Kitchen fully stocked with everything you would need. Lake view & backyard were amazing! Lots of fun using kayaks & canoes."
United States
Rose Angela M.
$489 nightly
The price is $546
Oct 23 - Oct 24
Total with taxes and fees
Cozy Cottage-Sunset On The Lake
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

7. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"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!! "
United States
Samantha G.
$547 nightly
The price is $578
Oct 28 - Oct 29
Total with taxes and fees
Treetop Hideaway in Tyringham
A compact RV kitchen with a stove, sink, and cabinets, a dining area with a bench, and a window with a view of greenery.

8. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"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...
United States
hannah w.
$179 nightly
The price is $200
Oct 6 - Oct 7
Total with taxes and fees
Cozy Camper tucked into the woods
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

9. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
$420 nightly
The price is $444
Sep 30 - Oct 1
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
$305 nightly
The price is $341
Oct 28 - Oct 29
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

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

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
$310 nightly
The price is $346
Oct 8 - Oct 9
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

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

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
$766 nightly
The price is $856
Oct 1 - Oct 2
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A cozy room with two beds, large windows, and a view of a snowy landscape.

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

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
$250 nightly
The price is $279
Oct 5 - Oct 6
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
A modern two-story house with large windows and a balcony.

14. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (12 reviews)
"Thanks for a great stay"
United States
Andrea M.
$570 nightly
The price is $637
Sep 30 - Oct 1
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

15. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
$284 nightly
The price is $317
Sep 30 - Oct 1
Total with taxes and fees
Riverside Retreat in the Berkshires
A house with a porch, a garden with pink flowers, and a stone wall along the road.

16. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (152 reviews)
"Great location"
United States
Will G.
$335 nightly
The price is $354
Oct 6 - Oct 7
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

17. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
$782 nightly
The price is $873
Oct 18 - Oct 19
Total with taxes and fees
Stylish Mid-century Modern Berkshires Cape
A covered outdoor seating area with two chairs and a view of a grassy landscape.

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

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
$284 nightly
The price is $317
Oct 1 - Oct 2
Total with taxes and fees
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

19. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
$654 nightly
The price is $730
Oct 4 - Oct 5
Total with taxes and fees
5BR Berkshire Home Mins To The Mountain
A modern living room with a sofa, armchair, coffee table, and TV.

20. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.4 out of 10, Exceptional, (3 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
$526 nightly
The price is $587
Oct 5 - Oct 6
Total with taxes and fees
Spacious Central Berkshires Home for Groups
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

Berkshires Untold

Berkshires Untold

8/10 Good
"A very good place to stay"
Madhavi R 1-night trip
Posted 1 hour ago
Berkshires Untold

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 $121 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.