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Middlefield Holiday Rentals

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Holiday Rentals in Middlefield

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2096)
"Great place!"
United States
Nicole
The price is AU$175
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (983)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is AU$241
includes taxes & fees
26 Oct - 27 Oct
Jiminy Peak Mountain Resort
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"All as promised!"
United States
Arthur
The Ponds at Foxhollow
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$403
includes taxes & fees
3 Nov - 4 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
United States
Stephanie R.
The Kemble- Built by a US Secretary of State in Lenox
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AU$1,114
includes taxes & fees
29 Oct - 30 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,731
includes taxes & fees
28 Oct - 29 Oct
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (31)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Peace and quiet on the lake
9.6 out of 10, Exceptional, (226)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is AU$761
includes taxes & fees
26 Oct - 27 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (132)
"We really enjoyed our stay. Watching all the wildlife come and go around the pond was a highlight. Thanks!"
United States
Anonymous traveller
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.8 out of 10, Exceptional, (19)
"Very friendly hosts, great location. "
United States
Dan M.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
9.8 out of 10, Exceptional, (70)
"Beautiful location, very spacious, comfortable and clean."
United States
Aubrey G.
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (70)
"This was our second time staying here and we had a great time!"
United States
Andy L.
The price is AU$435
includes taxes & fees
29 Oct - 30 Oct
The Creation Station is a cozy place so make yourself at home.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Private Island - Largest Fresh Water Reservoir in Mass
8.6 out of 10, Excellent, (9)
"We had a great time. The owner Bill was a great host."
United States
Drew D.
Private Island - Largest Fresh Water Reservoir in Mass
Westfield Vacation Rental w/ Porch, Pets Welcome!
3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (228)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
United States
Donald G.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (69)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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

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 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$175 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?

Amore Estate - beautiful room with many places to explore and relax in.: This holiday home rental outside of Middlefield offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Glendale Falls 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.