Romantic Hotels in Western Massachusetts
Massachusetts
United States of America
Romantic Hotels
Expedia.com.au

Western Massachusetts Travel Guide Hotels in Western Massachusetts Flights to Western Massachusetts Activities in Western Massachusetts Car Hire in Western Massachusetts Western Massachusetts Holiday Packages Holiday Rentals in Western Massachusetts

A sunset with a vibrant sky, a tall street lamp, and silhouettes of trees.

Romantic Hotels & Resorts in Western Massachusetts from AU$160

Where to?

Dates

your current months are November, 2026 and December, 2026.

November 2026

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

SunSunday

December 2026

MonMonday

TueTuesday

WedWednesday

ThuThursday

FriFriday

SatSaturday

SunSunday

Travellers

Room 1

Adults

ChildrenAges 0 to 17

Need to book 9 or more rooms?

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 prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Western Massachusetts romantic hotels

Two Adirondack chairs facing a river with a forested hill in the background.

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

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

1. The Yankee Inn

The Yankee Inn

2.5 star property

Lenox

9.2 out of 10, Wonderful, (1,003 reviews)

9.2/10

Wonderful

(1,003 reviews)

"What a beautiful stay. Room was so clean ! Great food selection for breakfast."

Stephanie

The price is AU$178

AU$178

includes taxes & fees

20 Nov - 21 Nov

The Yankee Inn

A hotel room with a bed, a television, a wardrobe, and a bathroom visible through an open door.

2. Garden Gables

Garden Gables

4.0 star property

Lenox

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Lovely place!"

Eyee

The price is AU$306

AU$306

includes taxes & fees

10 Nov - 11 Nov

Garden Gables

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lodge with a large building and a dock by a lake, surrounded by forest.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A dining area with large windows, wooden furniture, and a view of a lake.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property

Lee

9.2 out of 10, Wonderful, (1,001 reviews)

9.2/10

Wonderful

(1,001 reviews)

"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"

Gustavo

The price is AU$171

AU$171

includes taxes & fees

3 Dec - 4 Dec

The Black Swan Lee - Lenox, an Ascend Collection Hotel

An outdoor patio with white chairs and tables, a central fire feature, and string lights.

A bar area with a wooden counter, bar stools, and a variety of bottles and glasses.

A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

A hotel with a sign reading "D. HOTEL & SUITES" on the facade.

4. D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property

Holyoke

9.2 out of 10, Wonderful, (2,092 reviews)

9.2/10

Wonderful

(2,092 reviews)

"Very comfortable beds nice clean bathroom Excellent hot breakfast"

Luke

The price is AU$193

AU$193

includes taxes & fees

10 Dec - 11 Dec

D. Hotel Suites & Spa

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

5. Berkshires Untold

Berkshires Untold

3.5 star property

Lenox

9.0 out of 10, Wonderful, (1,068 reviews)

9.0/10

Wonderful

(1,068 reviews)

"Very nice place beautiful view"

Brian

The price is AU$171

AU$171

includes taxes & fees

17 Nov - 18 Nov

Berkshires Untold

A two-story house with a red door, green shutters, and a snow-covered front yard.

A wooden gazebo with a peaked roof, surrounded by a gravel area with potted plants.

A red building with white trim, surrounded by lush greenery and fruit trees.

A dining area with round tables, chairs, and a kitchen counter with a refrigerator.

6. Centennial House

Centennial House

3.5 star property

Northfield

9.8 out of 10, Exceptional, (194 reviews)

9.8/10

Exceptional

(194 reviews)

"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."

Alan

The price is AU$268

AU$268

includes taxes & fees

15 Nov - 16 Nov

Centennial House

A cozy room with a bed, breakfast area, and a wall with Alice in Wonderland-themed decor.

A two-story house with a front porch, a number 20 sign, and a pathway leading to the entrance.

A room with a bed, a chair, a desk, and a globe on a stand.

A living room with two armchairs, a coffee table, a lamp, a mirror, and a chandelier.

7. Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast

3.5 star property

Liberty Heights

9.0 out of 10, Wonderful, (469 reviews)

9.0/10

Wonderful

(469 reviews)

"Room was not only clean and comfortable but unique and charming. Loved the beautiful woodwork, built in fish tank, and electric fireplace in the o’Leary room. The owner is also very kind and goes above and beyond to care for her guests."

Samantha

The price is AU$160

AU$160

includes taxes & fees

24 Nov - 25 Nov

Naomi's Inn Bed & Breakfast

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

A hallway with a collection of plates on the walls, leading to a staircase.

Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

8. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 star property

North Adams

9.4 out of 10, Exceptional, (529 reviews)

9.4/10

Exceptional

(529 reviews)

"Great stay"

Ram

The price is AU$301

AU$301

includes taxes & fees

8 Dec - 9 Dec

The Porches Inn at Mass MoCA

A large, historic building with a prominent tower and a well-lit entrance labeled "Bollywood".

A spacious outdoor seating area with a fire feature, white brick walls, and multiple windows with shutters.

A long dining table set with white tableware, flanked by windows and a skylight.

A spacious living room with a fireplace, comfortable seating, and elegant chandeliers.

9. Inn on Boltwood

Inn on Boltwood

3.0 star property

Amherst

9.4 out of 10, Exceptional, (900 reviews)

9.4/10

Exceptional

(900 reviews)

"the wonderful stay!"

Yong

The price is AU$335

AU$335

includes taxes & fees

12 Nov - 13 Nov

Inn on Boltwood

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

10. The Red Lion Inn

The Red Lion Inn

3.5 star property

Stockbridge

8.8 out of 10, Excellent, (1,012 reviews)

8.8/10

Excellent

(1,012 reviews)

"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."

Lisabeth

The price is AU$329

AU$329

includes taxes & fees

17 Nov - 18 Nov

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

Top Western Massachusetts Hotel Reviews

A two-story building with a sign reading "Chambéry Inn".

A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

Chambery Inn

Lee

10/10 Excellent

The room was large and comfortable and had a gas fire. It was also on ground floor so easy access for suitcases. Staff were helpful and pleasant and it is close to lots of restaurants within walking distance.

Anonymous traveller

Reviewed October 28, 2019Reviewed October 28, 2019

Chambery Inn

Inn on Boltwood

Amherst

10/10 Excellent

My family and I recently stayed at the Inn on Boltwood during a short trip to western Massachusetts. The hotel made for a very pleasant, comfortable stay ! We loved our rooms and enjoyed drinks and nibbles in the bar . The hotel is also within easy driving distance of neighbouring Northampton and local universities . We would highly recommend The Inn on Boltwood to anyone planning to travel to the Amherst area !

Alexander

Reviewed April 28, 2022Reviewed April 28, 2022

Inn on Boltwood

The Yankee Inn

Lenox

10/10 Excellent

A convenient location. Excellent well appointed and clean room. An excellent breakfast provided. Would stay again.

Lawrence

Reviewed April 16, 2026Reviewed April 16, 2026

The Yankee Inn

Explore a world of travel with Expedia

Lodging
Flights
Packages
Cars

Cabin Rentals in Adams
Standard Link for Cabin Rentals in Adams
Adams Hotels
Standard Link for Adams Hotels
The Inn At Crumpin Fox
Standard Link for The Inn At Crumpin Fox
Colrain Hotels
Standard Link for Colrain Hotels
Drury Hotels
Standard Link for Drury Hotels
Luxury Hotels in Goshen
Standard Link for Luxury Hotels in Goshen
B&B in Greenfield
Standard Link for B&B in Greenfield
Hadley Hotels
Standard Link for Hadley Hotels
Heath Hotels
Standard Link for Heath Hotels
Holden Hotels
Standard Link for Holden Hotels
Charming historic cottage on scenic road to Mt. Greylock
Standard Link for Charming historic cottage on scenic road to Mt. Greylock
Lee Hotels
Standard Link for Lee Hotels
33 Main
Standard Link for 33 Main
The Whitlock
Standard Link for The Whitlock
Great Wolf Lodge Boston / Fitchburg
Standard Link for Great Wolf Lodge Boston / Fitchburg
The Colonial Hotel
Standard Link for The Colonial Hotel
B&B in Longmeadow
Standard Link for B&B in Longmeadow
Ludlow Hotels
Standard Link for Ludlow Hotels
Cabin Rentals in Mohawk Trail State Forest
Standard Link for Cabin Rentals in Mohawk Trail State Forest
Sweet Suite in Montague near Colleges and Downtown Turners Falls Great Falls.
Standard Link for Sweet Suite in Montague near Colleges and Downtown Turners Falls Great Falls.
Sleek Butternut Ski Chalet Lakefront with Hot Tub & Sauna Near Great Barrington
Standard Link for Sleek Butternut Ski Chalet Lakefront with Hot Tub & Sauna Near Great Barrington
B&B in Petersham
Standard Link for B&B in Petersham
Petersham Hotels
Standard Link for Petersham Hotels
Fairbridge Inn Express
Standard Link for Fairbridge Inn Express
Pittsfield Hotels
Standard Link for Pittsfield Hotels
B&B in Royalston
Standard Link for B&B in Royalston
Royalston Hotels
Standard Link for Royalston Hotels
Sheffield Hotels
Standard Link for Sheffield Hotels
B&B in Springfield
Standard Link for B&B in Springfield
Candlewood Suites West Springfield by IHG
Standard Link for Candlewood Suites West Springfield by IHG
The Ellery
Standard Link for The Ellery
Springfield Hotels
Standard Link for Springfield Hotels
Sterling Hotels
Standard Link for Sterling Hotels
The Red Lion Inn
Standard Link for The Red Lion Inn
Hotels near Tanglewood Music Center
Standard Link for Hotels near Tanglewood Music Center
Serviced Apartments in The Berkshires
Standard Link for Serviced Apartments in The Berkshires
Hotels near Wachusett Mountain Ski Area
Standard Link for Hotels near Wachusett Mountain Ski Area
Ware Hotels
Standard Link for Ware Hotels
Webster Hotels
Standard Link for Webster Hotels
Cabin Rentals in Western Massachusetts
Standard Link for Cabin Rentals in Western Massachusetts
Westminster Hotels
Standard Link for Westminster Hotels
Cabin Rentals in Williamstown
Standard Link for Cabin Rentals in Williamstown
Lgbt Welcoming Hotels in Williamstown
Standard Link for Lgbt Welcoming Hotels in Williamstown
Beechwood Hotel
Standard Link for Beechwood Hotel
Lgbt Welcoming Hotels in Worcester
Standard Link for Lgbt Welcoming Hotels in Worcester
Worcester Hotels
Standard Link for Worcester Hotels

Flights to Amherst
Standard Link for Flights to Amherst
Flights to Becket
Standard Link for Flights to Becket
Flights to Shrewsbury
Standard Link for Flights to Shrewsbury
Flights to Springfield
Standard Link for Flights to Springfield
Flights to Williamstown
Standard Link for Flights to Williamstown
Flights to Worcester
Standard Link for Flights to Worcester
Flights from Worcester Regional
Standard Link for Flights from Worcester Regional
Flights from Bellingham (BLI) to Worcester (ORH)
Standard Link for Flights from Bellingham (BLI) to Worcester (ORH)
Flights from Cleveland (CLE) to Pittsfield (PSF)
Standard Link for Flights from Cleveland (CLE) to Pittsfield (PSF)
Flights from Lafayette (LFT) to Worcester (ORH)
Standard Link for Flights from Lafayette (LFT) to Worcester (ORH)
Flights from Sydney (SYD) to Worcester (ORH)
Standard Link for Flights from Sydney (SYD) to Worcester (ORH)

Visit Great Barrington
Standard Link for Visit Great Barrington
Hadley Farm Museum
Standard Link for Hadley Farm Museum
National Shrine of the Divine Mercy
Standard Link for National Shrine of the Divine Mercy
Rowe Holidays
Standard Link for Rowe Holidays

Car hire Cheshire
Standard Link for Car hire Cheshire
Car hire Dudley
Standard Link for Car hire Dudley
Car hire Lenox
Standard Link for Car hire Lenox
Car hire Worcester
Standard Link for Car hire Worcester
Thrifty Car Rental Rental Cars in Florence
Standard Link for Thrifty Car Rental Rental Cars in Florence

Romantic Hotels & Resorts in Western Massachusetts from AU$160

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Western Massachusetts romantic hotels

1. The Yankee Inn

2. Garden Gables

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

4. D. Hotel Suites & Spa

5. Berkshires Untold

6. Centennial House

7. Naomi's Inn Bed & Breakfast

8. The Porches Inn at Mass MoCA

9. Inn on Boltwood

10. The Red Lion Inn

Top Western Massachusetts Hotel Reviews

Chambery Inn

10/10 Excellent

Explore a world of travel with Expedia