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

Best Resorts in Middlefield

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Middlefield

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

1. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Very nice and convenient hotel."
United States
Karen
$100 nightly
The price is $112
Sep 28 - Sep 29
Total with taxes and fees
The Yankee Inn
A building with a flat roof, multiple windows, and a satellite dish.

2. Becket Motel

Becket Motel
2.5 star property
Becket
6.6 out of 10, (63 reviews)
"Comfortable stay "
United States
Paul
$123 nightly
The price is $137
Sep 8 - Sep 9
Total with taxes and fees
Becket Motel
A calm lake at dusk with a wooden dock and two chairs facing the water.

3. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.6 out of 10, Exceptional, (13 reviews)
"excellent lakeside view"
United States
mike
$139 nightly
The price is $155
Sep 9 - Sep 10
Total with taxes and fees
Berkshire Lake Lodge
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

4. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very Good, (1,006 reviews)
"It was clean and amenities were above average."
United States
Prasanna
$90 nightly
The price is $100
Sep 7 - Sep 8
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

5. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (907 reviews)
"Stay again"
United States
irene
$78 nightly
The price is $87
Sep 8 - Sep 9
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

6. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,008 reviews)
"Very nice stay"
United States
Christine
$110 nightly
The price is $122
Sep 23 - Sep 24
Total with taxes and fees
Quality Inn Lee - Lenox South
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

7. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,001 reviews)
"enjoyable stay"
United States
James
$128 nightly
The price is $142
Sep 23 - Sep 24
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

8. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (890 reviews)
"It was very nice and everyone was extremely helpful"
United States
ERICIA
$61 nightly
The price is $68
Sep 3 - Sep 4
Total with taxes and fees
FairBridge Inn Express
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,115 reviews)
"Clean & comfortable stay"
United States
Robert
$113 nightly
The price is $126
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

10. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (916 reviews)
"Excellent room super clean!"
United States
Adriana
$73 nightly
The price is $82
Sep 3 - Sep 4
Total with taxes and fees
Berkshire Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

11. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
$121 nightly
The price is $135
Sep 30 - Oct 1
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with clear water, tiled floors, and a blue wall.

12. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (182 reviews)
"Clean & easy to stay there"
United States
Steve
$118 nightly
The price is $132
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

13. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (439 reviews)
"Host was very pleasant and extremely help with directions. Would definitely recommend"
United States
Joann
$101 nightly
The price is $113
Sep 8 - Sep 9
Total with taxes and fees
Sunset Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

14. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,010 reviews)
"Standard roadside motel converted into a boutique hotel with great food and services. Will stay again if in the area."
United States
David
$145 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
Berkshires Untold
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

15. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,000 reviews)
"Look good for being under constructikn"
United States
Debra
$118 nightly
The price is $132
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

16. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very Good, (405 reviews)
"Large, clean, comfortable suite."
United States
Rena
$89 nightly
The price is $100
Sep 14 - Sep 15
Total with taxes and fees
The Central Downtown Inn & Suites
A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

17. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (693 reviews)
"Have stayed here several times and it is a basic, decent place. It is in a great location, relatively clean and comfortable. Would return again."
United States
Anna
$69 nightly
The price is $77
Sep 13 - Sep 14
Total with taxes and fees
Econo Lodge Lee - Great Barrington
A large house with a covered patio area featuring outdoor seating and a fire pit.

18. The Whitlock

The Whitlock
2.0 star property
Lenox
8.4 out of 10, Very Good, (364 reviews)
"Lovely room, nice amenities."
United States
Constance
$144 nightly
The price is $160
Sep 8 - Sep 9
Total with taxes and fees
The Whitlock
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

19. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (704 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$146 nightly
The price is $163
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

20. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,007 reviews)
"It is a little pricey for what you get but we loved the property and the area and will be back!"
United States
Patricia
$215 nightly
The price is $240
Sep 30 - Oct 1
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlefield Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."
Janet L. 2-night trip
Posted 4 hours ago
Quality Inn Great Barrington

Find out more about Middlefield

Middlefield Resorts information

Number of reviews
12,310
Accommodation
12 Resorts
Lowest Price
$68
Highest Price
$240

Frequently asked questions

What is Middlefield like for a resort vacation?
Longing for a relaxing getaway? You deserve the comforts of a resort, where you can find everything you need for your stay from tasty dining options to activities and shopping. Browse the resort options in the area and discover the best one for you, whether you envision yourself sipping drinks by a sprawling pool or heading to the spa for a deep-tissue massage.
What's a favorite resort for my stay in Middlefield?
Our highest-rated resorts near Middlefield: COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 20.1 mi (32.4 km) from Middlefield. Has ski-in/ski-out access, a fitness center, and beach sun loungers. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 20.1 mi (32.3 km) from Middlefield. Enjoy the ski-in/ski-out access, fitness center, and garden. Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort - Situated just a 5-minute walk from Jiminy Peak Mountain Resort. 20.1 mi (32.3 km) from Middlefield. Access to a fitness center, an indoor pool, and an outdoor pool.
What can I do in Middlefield?
Skyline Trail and Fox Den Wildlife Management Area are a few of the interesting sights to visit. In the area, other attractions include Jacob's Pillow and Goose Pond Reservation.
What's the seasonal weather like in Middlefield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Middlefield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What's the best way to get to and around Middlefield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 15.1 mi (24.3 km) away from the heart of the city. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 19.6 mi (31.6 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia