A lake with a rocky shoreline and a forested island.

Historic Hotels & Resorts in Western Massachusetts from NZ$244

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Check availability on Western Massachusetts Historic Hotels

Tonight
30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.
An outdoor cafe with tables and chairs, surrounded by hanging flower baskets and a brick building in the background.
A hotel room with a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.

1. Hotel Northampton

Hotel Northampton
Northampton
United States
Beth
NZ$244
includes taxes & fees
12 Oct - 13 Oct
Hotel Northampton
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

2. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
NZ$428
includes taxes & fees
19 Oct - 20 Oct
The Red Lion Inn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.
A spacious living area with a stone fireplace, comfortable seating, and a dining area.
A snow-covered outdoor area with a fire pit, tables, and chairs, indicating a winter resort setting.
A living room with a sofa, a coffee table, a TV, and a window with curtains.

3. 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
United States
Kristina L.
NZ$432
includes taxes & fees
6 Oct - 7 Oct
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country 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 room with a wooden bench, a table, and a door with glass panels.
A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.

4. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
NZ$854
includes taxes & fees
13 Oct - 14 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 cozy living room with a stone wall, a fireplace, and a chandelier.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.
A staircase with a stone wall on one side and a wooden handrail on the other.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
NZ$436
includes taxes & fees
13 Oct - 14 Oct
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 living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.
A wooden deck with a grill, a table, and chairs.
A two-story house with a front porch, a small garden, and a mailbox.

6. 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.
NZ$694
includes taxes & fees
1 Oct - 2 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 room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.
A two-story house with a garage, a driveway, and a river in the background.
A living room with a large window, a ceiling fan, a television, a glass coffee table, a patterned rug, and two chairs.

7. 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
Kristi M.
NZ$903
includes taxes & fees
29 Oct - 30 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with white cabinets and a built-in knife block.
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.

8. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
NZ$1,336
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, a red rug, a bookshelf, and a chair.
A two-story house with a gravel driveway leading to a garage.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.

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.
NZ$2,288
includes taxes & fees
16 Oct - 17 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
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Top Western Massachusetts Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"G"
Albert 2-night trip
Posted 7 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 1 day ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 2 days ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice room. Exceptionally clean. Great staff"
Daniel 3-night trip
Posted 2 days ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 7 days ago
Hotel Downstreet, an Ascend Collection Hotel

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