A lake with a rocky shoreline and a forested island.

Find Historic Hotels in Western Massachusetts, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Western Massachusetts Historic Hotels

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Western Massachusetts historic hotels

A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.
A hotel room with two beds, a TV, a desk, and a chair.

1. Hotel Northampton

Hotel Northampton
Northampton
United States
Beth
AED 545
AED 609 total
includes taxes & fees
20 Oct - 21 Oct
Hotel Northampton
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.

2. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 579
AED 829 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A kitchen with white cabinets, a wooden dining table, and pendant lights.
A cozy room with a wooden bench, a small table, and a chair.
A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.
A room with a wooden bench, a table, and a door with glass panels.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
AED 841
AED 1,781 total
includes taxes & fees
19 Oct - 20 Oct
A roomy remodeled retreat close to MassMoCA
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.
A staircase with a stone wall on one side and a wooden handrail on the other.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.
A cozy living room with a stone fireplace, leather sofas, a wooden coffee table, and a chandelier.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
AED 551
AED 994 total
includes taxes & fees
2 Nov - 3 Nov
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
A two-story house with a front porch, a small garden, and a mailbox.
A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.
A wooden deck with a grill, a table, and chairs.

5. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
United States
Anita T.
AED 691
AED 1,452 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A patio with a table and chairs, a grill, and a view of a lake.
A cozy living room with a fireplace, a bookshelf, a dining table with checkers, and a large window with a view of the outdoors.
A room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.
A living room with a large window, a ceiling fan, a television, a glass coffee table, a patterned rug, and two chairs.

6. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
United States
Mike
AED 1,031
AED 1,795 total
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A hotel with a central building, outdoor seating area, and a covered patio.
A two-story cabin with a deck, a driveway, and a lake view.
A well-maintained lawn with a stone pathway leading to a wooden building with a balcony.
A room with a view of a lake, wicker furniture, and a table with decorative items.

7. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
United States
Anonymous traveler
AED 1,010
AED 1,965 total
includes taxes & fees
2 Nov - 3 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.
A modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.

8. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,008
AED 2,154 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A modern kitchen with white cabinets, a large island, and a skylight.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.
A two-story house with a gravel driveway leading to a garage.
A bedroom with a large bed, a red rug, a bookshelf, and a chair.

9. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
United States
stephen r.
AED 3,269
AED 5,410 total
includes taxes & fees
28 Oct - 29 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
View all properties

Top Western Massachusetts Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Staff was extremely helpful"
Frances 1-night trip
Posted less than an hour ago
The Yankee Inn
D. Hotel Suites & Spa

D. Hotel Suites & Spa

8/10 Good
"Beautiful property with nice restaurant. Reception and check in was confusing as the auto checkin didn’t work. The staff was ok. Disappointed that the sauna was not available as this was the reason we chose your hotel. No where did it indicate we needed a reservation for the use of this. Also we were charged a fee to use facilities which the sauna wasn’t available so disappointed we paid for something. It available."
Topside 1-night trip
Posted 1 hour ago
D. Hotel Suites & Spa
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 13 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The hotel is in a good location. There are some good restaurants within walking distance. Only one complaint is that the bathroom fan is very loud."
Cynthia 3-night trip
Posted 21 hours ago
Quality Inn Great Barrington
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"Good"
Kenny 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Springfield MA
Hilton Garden Inn-Springfield, MA

Hilton Garden Inn-Springfield, MA

10/10 Excellent
"I like the convenience of the location. Can get to places very quickly. And immediately back on the highway."
Edward 3-night trip
Posted 4 days ago
Hilton Garden Inn-Springfield, MA

Explore a world of travel with Expedia