Middlefield Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Middlefield holiday rentals

Exterior

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,301 reviews)
"Great place in Williamstown. Near ski resort."
United States
Jason
The price is HK$814
HK$995 total
includes taxes & fees
15 Mar - 16 Mar
Vacation Village in the Berkshires
Property grounds

Holiday Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is HK$1,565
HK$2,871 total
includes taxes & fees
14 Mar - 15 Mar
Big farmhouse in the foothills of the Berkshires
1 bedroom, desk, iron/ironing board, travel cot

Holiday Home in Easthampton Ma.

The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (75 reviews)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is HK$1,409
HK$2,168 total
includes taxes & fees
16 Mar - 17 Mar
The Creation Station is a cozy place so make yourself at home.
Interior

Cottage in Charlemont

12-acre Vacation Rental in the Berkshires!
3.0 star property
The price is HK$1,902
HK$4,261 total
includes taxes & fees
14 Mar - 15 Mar
12-acre Vacation Rental in the Berkshires!
Daily to-go breakfast for a fee

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,166
HK$1,303 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
Property grounds

Villa in Whately

Cozy Valley View Post & Beam Villa!
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is HK$4,696
HK$5,919 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Valley View Post & Beam Villa!
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$2,011
HK$4,196 total
includes taxes & fees
7 Apr - 8 Apr
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Smart TV, books

Holiday Home in Sherwood Forest

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,254
HK$3,000 total
includes taxes & fees
15 Mar - 16 Mar
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior

Holiday Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$1,755
HK$4,321 total
includes taxes & fees
15 Mar - 16 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

Apartment in Northampton

Button's Modern Luxury Walkup Downtown Northampton
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is HK$1,854
HK$3,819 total
includes taxes & fees
15 Mar - 16 Mar
Button's Modern Luxury Walkup Downtown Northampton
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,296
HK$2,156 total
includes taxes & fees
15 Mar - 16 Mar
Home in Great Barrington
Exterior

Camping in Williamstown

Huttopia Berkshires
1.0 star property
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$1,317
HK$1,471 total
includes taxes & fees
15 Mar - 16 Mar
Huttopia Berkshires
Property grounds

Holiday Home in Charlemont

Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is HK$1,369
HK$3,453 total
includes taxes & fees
25 Mar - 26 Mar
Riverbend Berkshire East Basecamp - 3 bedrooms available
TV, fireplace, printers

Holiday Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,452
HK$10,428 total
includes taxes & fees
14 Mar - 15 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Outdoor dining

Holiday Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,106
HK$3,865 total
includes taxes & fees
15 Mar - 16 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior

Condo in Hancock

UNIQUE - 1BR Country Condo @ Jiminy Peak
9.8 out of 10, Exceptional, (17 reviews)
"lovely place to stay"
United States
Nancy P.
The price is HK$1,754
HK$3,699 total
includes taxes & fees
20 Mar - 21 Mar
UNIQUE - 1BR Country Condo @ Jiminy Peak
Interior

Holiday Home in Great Barrington

Cozy Riverside Berkshires Retreat
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,585
HK$2,479 total
includes taxes & fees
15 Mar - 16 Mar
Cozy Riverside Berkshires Retreat
Fridge, microwave, oven, stovetop

Holiday Home in Lee

Spacious 5-bedroom house in charming Lee with WiFi
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$2,935
HK$5,744 total
includes taxes & fees
22 Mar - 23 Mar
Spacious 5-bedroom house in charming Lee with WiFi
TV

Holiday Home in Monterey

Treetop Hideaway in Tyringham
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,066
HK$4,368 total
includes taxes & fees
16 Mar - 17 Mar
Treetop Hideaway in Tyringham
Smart TV, books

Holiday Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is HK$1,409
HK$3,602 total
includes taxes & fees
15 Mar - 16 Mar
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Clean. Staff was great. Easy commute to mountain. "
Michael 2-night trip
Posted 7 hours ago
Vacation Village in the Berkshires

Find out more about Middlefield

Search for holiday rentals in Middlefield on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlefield using one of the methods below:

  • View our selection of featured holiday rentals in Middlefield
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Look no further and take a look at our great range of rental properties in Middlefield!

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?

Family Ski Getaway in the Berkshires: This holiday home rental outside of Middlefield is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Middlefield?

While exploring the area, visit family-friendly sights like Berkshire Scenic Railway 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 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.