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Middlefield Holiday Rentals

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Holiday Rentals in Middlefield

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (860)
"This is a sweet property. I visited in the summer. The dining options were great. The country store is awesome. I love how the rooms are suites. They feel like small apartments. I like that they have kitchens. The bed was comfortable. The ac is loud but at least it works well and it drowns out other noises. I needed a late check out and they were very cool about it. They let me hang out at the pool and then shower at the spa because I was like of stuck there several hours after check out time....
The price is AU$261
per night
23 June - 24 June
Jiminy Peak Mountain Resort
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (35)
"Very clean and nice apartment in a pleasant little city."
The price is AU$394
per night
23 June - 24 June
Cozy apartment located in quiet Williamsburg
Peace and quiet on the lake
9.6 out of 10, Exceptional, (186)
"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"
Peace and quiet on the lake
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (5)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (118)
"Comfortable, quiet and convenient country location. This is our third time staying at the property for fishing and exploring the Deerfield and Westfield rivers and we will definitely return."
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (206)
"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"
Berkshire Village Carriage House - Super Private!!
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (52)
"Wonderful place to stay, had a great time lots of instruments to try, had lots of space to spread out and hangout, the hot tub was very nice and clean. Overall had a fantastic stay the lighted walkway is amazing! All the amenities available where also great, Jon was a great host and we had a great time speaking with him!"
The price is AU$425
per night
1 July - 2 July
The Creation Station is a cozy place so make yourself at home.
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is AU$410
per night
24 June - 25 June
Perfect Vacation Get Away - Historical New Marlborough
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (21)
"The rental property was just as described online. We had a very relaxing time. We also enjoyed playing all the games provided. This is a beautiful location and very quiet area. We loved sitting out in the hot tub at night looking up at the stars. Really special experience."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
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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.

Middlefield Holiday Home Travel Info

Other types of properties in Middlefield you may be interested in

Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (268)
"Wonderful little get away with the family - the hotel was lovely, we had a great breakfast and a hike across the street at Kennedy Park. "
The price is AU$199
per night
25 June - 26 June
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1001)
"We had a good experience here! The staff was AWESOME! They were very helpful in checking in and gave us good info. They have a bar but it was not open during the times we were in and out. The breakfast was good and we enjoyed the omelet. Its only on the weekend--wish it was every day! The pool was warm and the hot tub was nice! Love that the have shampoo, conditioner and soap in the shower. Our only complaint was our air conditioner wasnt the best..our room didnt get as cool as we wanted but not...
The price is AU$209
per night
24 June - 25 June
The Yankee, Trademark Collection by Wyndham
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (901)
"Revisiting this icon where we had not been since we were kids. The charm remains, the staff is excellent, the food and cocktails/wine great. They have options for hearing live music in their renovated den. The bedroom in the extended building was quite disappointing however. Very dated, doesn’t function well for modern travelers: bathroom tub was tough to get in and out and bathroom not organized for products. Overall a well run icon, hopefully some more upgrades continue to modernize rooms."
The price is AU$368
per night
24 June - 25 June
The Red Lion Inn
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.

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 favourite 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 depend 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 AU$261 per night. Entering your travel dates in the search wizard might find you 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?

Cozy apartment located in quiet Williamsburg: This holiday home rental outside of Middlefield is in a rural location, and equipped with air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Middlefield?

Expedia has 3 holiday 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. October Mountain State Forest and Jacob's Pillow 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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