Find Historic Hotels in Western Massachusetts, MA

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Check availability on Western Massachusetts Historic Hotels

Our top choices for Western Massachusetts historic hotels

Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
The price is AED 545
AED 773 total
includes taxes & fees
14 Jan - 15 January 2026
The Red Lion Inn
2 restaurants, breakfast, lunch, dinner served; American cuisine
Hotel Northampton

Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1000)
"Beautiful historic property with great dining options."
United States
Mark
Hotel Northampton
Exterior
Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG
2.5 star property
Metro Center
9.0 out of 10, Wonderful, (1078)
"Great stay"
United States
Desiree
The price is AED 419
AED 475 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn Express Springfield Downtown by IHG
Reception
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
7.6 out of 10, Good, (103)
"Clean room, friendly staff, good mattress. Not fancy or plush, but perfect for a one or two night place to land while attending events at the Big E. "
United States
Kim
The price is AED 372
AED 426 total
includes taxes & fees
21 Dec - 22 Dec
Baldwin Inn & Suites, SureStay Collection by Best Western
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 2,112
AED 2,317 total
includes taxes & fees
16 Dec - 17 Dec
Inn at Kenmore Hall
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AED 386
AED 857 total
includes taxes & fees
16 Dec - 17 Dec
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Fridge, microwave, oven, stovetop
Historic downtown house. Unscented products and sustainability practices.

Historic downtown house. Unscented products and sustainability practices.

Historic downtown house. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (7)
"We stayed here to move our daughter into Smith, and it was a great property in a beautiful area. Debra was incredibly responsive and helpful and made a stressful time much easier."
United States
Lindsay R.
The price is AED 1,543
AED 2,720 total
includes taxes & fees
31 Dec - 1 January 2026
Historic downtown house. Unscented products and sustainability practices.
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is AED 445
AED 482 total
includes taxes & fees
31 Dec - 1 January 2026
The Carriage Barn Inn
Standard Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Econo Lodge Sturbridge Route 20

Econo Lodge Sturbridge Route 20

Econo Lodge Sturbridge Route 20
2.0 star property
Sturbridge
7.0 out of 10, Good, (1002)
"Great people,very nice and friendly. Clean room would stay again "
United States
Dennis
The price is AED 241
AED 269 total
includes taxes & fees
13 Jan - 14 January 2026
Econo Lodge Sturbridge Route 20
Exterior detail
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (95)
"This was an incredibly beautiful place to spend a restful weekend. "
United States
Meagan M.
The price is AED 551
AED 986 total
includes taxes & fees
18 Dec - 19 Dec
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
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 Western Massachusetts Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"A magical, magical New England weekend at The Red Lion Inn. The room was so warm, the bed and pillows were so comfortable and just the right firmness. The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night. Check in was a breeze, staff were warm and welcoming. Highly recommend making reservations at their Tavern or Dining Area. Several small cafes and charming local shops close by for Christmas shopping"
Judith Pauline 1-night trip
Posted 1 hour ago
The Red Lion Inn

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