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Best Resorts in Middlefield

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Jan 2 - Jan 4
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No exact matches found, but these alternatives could be just right

Recommended hotels in Middlefield

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"Very friendly and good Breakfast."
United States
Jesse
$76 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby
Hampton Inn Westfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (817)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
$116 nightly
The price is $130
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hampton Inn Westfield
Free daily buffet breakfast
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (904)
"We left too early for breakfast. Parking was fine "
United States
Virginia
$94 nightly
The price is $104
Jan 11 - Jan 12, 2026
Total with taxes and fees
Quality Inn Westfield - Springfield
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1006)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$93 nightly
The price is $103
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Front of property
The Ellery

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (928)
"Clean, lovely staff and breakfast "
United Kingdom
MICHAEL
$123 nightly
The price is $137
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Ellery
Exterior
River Valley Inn

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (99)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
$99 nightly
The price is $111
Dec 25 - Dec 26
Total with taxes and fees
River Valley Inn
Front of property
Hotel Northampton

Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1000)
"Very good stay"
United States
Richard
$165 nightly
The price is $184
Dec 25 - Dec 26
Total with taxes and fees
Hotel Northampton
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
$135 nightly
The price is $151
Jan 4 - Jan 5, 2026
Total with taxes and fees
Element Lenox Berkshires
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$100 nightly
The price is $112
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Restaurant
Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (959)
"Great welcome at front desk."
United States
RAYMAN
$130 nightly
The price is $146
Jan 13 - Jan 14, 2026
Total with taxes and fees
Hampton Inn Hadley-Amherst Area
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1000)
"My go to place for my ski weekends"
United States
Ryan
$76 nightly
The price is $85
Jan 7 - Jan 8, 2026
Total with taxes and fees
Quality Inn Great Barrington
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$98 nightly
The price is $109
Jan 2 - Jan 3, 2026
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Free daily on-the-go breakfast
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
2.5 star property
Northampton
7.2 out of 10, Good, (1000)
"Staff was great and the room was well appointed and clean. "
United States
Stephanie
$110 nightly
The price is $122
Jan 1 - Jan 2, 2026
Total with taxes and fees
Quality Inn & Suites Northampton - Amherst
Lobby
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
3.0 star property
Northampton
9.2 out of 10, Wonderful, (1000)
"An excellent stay. Wonderfully clean, friendly front desk staff and the breakfast buffet was actually good. Will definitely stay again."
United States
Joyce
$134 nightly
The price is $150
Jan 1 - Jan 2, 2026
Total with taxes and fees
Fairfield Inn & Suites Springfield Northampton/Amherst
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (710)
"Great hospitality "
United States
regina maria
$107 nightly
The price is $120
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (810)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Jan 1 - Jan 2, 2026
Total with taxes and fees
Monument Mountain Motel
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
United States
Robert
$105 nightly
The price is $116
Jan 5 - Jan 6, 2026
Total with taxes and fees
Shaker Mill Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
$79 nightly
The price is $89
Dec 25 - Dec 26
Total with taxes and fees
Berkshire Inn
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
$75 nightly
The price is $84
Dec 25 - Dec 26
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Dec 25 - Dec 26
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay! "
Brandon 3-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Middlefield

Middlefield Resorts information

Number of reviews
15,880
Accommodation
33 Resorts
Lowest Price
$74
Highest Price
$184

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 top-rated resort near Middlefield: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 14.1 mi (22.6 km) from Middlefield. Access to a sauna, a fitness center, and a terrace.
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 Chester Town Hall and Jacob's Pillow.
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.

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