Western Massachusetts Holiday Rentals, Massachusetts: Private House Rentals

A lake with a rocky shoreline and a forested island.

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Our top choices for Western Massachusetts hotels

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

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

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

A hotel room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.

1. D. Hotel Suites & Spa

Holyoke

Karen

Rp2.177.631

Rp2.548.065 total

includes taxes & fees

5 Oct - 6 Oct

A hotel with a covered entrance, a flag, and a sign.

A modern hotel lobby with a round wooden reception desk, a chandelier, and a large mirror with a crescent moon design.

A spacious living area with a fireplace, sofas, and a coffee table.

A hotel room with a bed, a sofa, a round coffee table, and a nightstand.

2. Comfort Inn & Suites Hadley - Amherst

Hadley

Mutharaju Ram Mohan

Rp2.571.766

Rp2.872.663 total

includes taxes & fees

26 Oct - 27 Oct

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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

3. The Yankee Inn

Lenox

William

Rp1.933.524

Rp2.159.818 total

includes taxes & fees

27 Oct - 28 Oct

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A spacious lobby with a fireplace, seating area, and a bar.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

4. Berkshire Mountain Lodge

Pittsfield

Robert

Rp1.425.067

Rp1.991.753 total

includes taxes & fees

1 Oct - 2 Oct

An outdoor patio area with seating, a fire feature, and a view of the building's exterior.

A modern bar area with a long counter, multiple screens, and a seating area with metal chairs.

A modern reception area with a wooden reception desk, seating area with sofas and chairs, and large windows providing natural light.

A hotel room with two beds, a large window with a view of trees, and a wall mural.

5. Courtyard by Marriott West Springfield

West Springfield

Christopher

Rp2.419.590

Rp2.769.221 total

includes taxes & fees

4 Oct - 5 Oct

A multi-story hotel with a prominent 'La Quinta' sign, featuring a symmetrical facade with evenly spaced windows and a central entrance.

A hotel room with two beds, a desk, a television, and a window with curtains.

A spacious lobby with wooden flooring, a reception desk, and two patterned armchairs.

A hotel dining area with multiple tables and chairs, a patterned carpet, and a reception desk in the background.

6. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center

Meris

Rp2.191.327

Rp2.486.060 total

includes taxes & fees

28 Sept - 29 Sept

A breakfast area with a counter, seating, and a menu display.

A modern living room with a sofa, armchair, and a small table.

A hotel lobby with reception desks, seating area, and a modern ceiling design.

A Holiday Inn Express hotel with large windows, a prominent 'Holiday Inn Express' sign, and classical architectural columns.

7. Holiday Inn Express Springfield Downtown by IHG

Metro Center

Casey

Rp1.852.960

Rp2.102.183 total

includes taxes & fees

26 Oct - 27 Oct

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

A spacious living room with large windows, a fireplace, and a variety of seating options.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

8. Vacation Village in the Berkshires

Williamstown

Jacob

Rp1.703.350

Rp2.099.038 total

includes taxes & fees

27 Sept - 28 Sept

A breakfast area with a waffle station, coffee machine, and various food options.

A hotel room with two beds, a nightstand, and a modern lamp.

An indoor swimming pool with a clear waterline, a metal ladder, and red chairs around the pool area.

A modern lounge area with blue seating, a coffee table, and decorative lighting.

9. Tru by Hilton Chicopee Springfield

Chicopee

SASHAWN

Rp2.187.389

Rp2.481.593 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

A bathroom with a bathtub, toilet, and shower curtain.

A hotel room with two beds, a sofa, a desk, a TV, and a picture on the wall.

A row of single-story motel buildings with a parking lot in front.

10. River Valley Inn

West Hatfield

Michael

Rp1.853.856

Rp2.070.661 total

includes taxes & fees

28 Sept - 29 Sept

A garden with a swing set, a blue chair, and a flower bed.

A breakfast buffet setup with cereal, milk, juice, and pastries.

A garden with a wooden pergola, potted plants, and a lawn with chairs.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

11. Maple Terrace Motel

Williamstown

Deborah

Rp2.309.487

Rp2.579.643 total

includes taxes & fees

27 Sept - 28 Sept

An indoor swimming pool with a pool lift, a changing room, and a view of the outside.

A spacious dining area with multiple tables and chairs, a sofa, and patterned curtains.

A hotel room with two beds, a desk with a flat-screen TV, a chair, and a bedside table with lamps.

A reception area with a wooden reception desk, framed pictures on the wall, a small plant, and a hallway leading to an exit.

12. Hampton Inn & Suites Springfield/Downtown

South End

Claire

Rp2.040.584

Rp2.315.043 total

includes taxes & fees

25 Oct - 26 Oct

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 a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.

13. Hotel Northampton

Northampton

Beth

Rp2.215.496

Rp2.474.732 total

includes taxes & fees

27 Sept - 28 Sept

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

A conference room with a long table, six chairs, a projector screen, and a brick wall.

A gazebo with a red roof and white walls, surrounded by trees and a brick building.

A conference table set for a meeting with chairs and folded red napkins.

14. The Inn At Crumpin Fox

Bernardston

Alan

Rp1.836.311

Rp2.051.147 total

includes taxes & fees

27 Sept - 28 Sept

A modern dining area with a long table, cushioned seating, and framed artwork on the wall.

A hotel conference room with round tables, chairs, and floral centerpieces.

A hotel room with a bed, two bedside tables with lamps, a nightstand, and a carpeted floor.

An outdoor patio area with a pergola, seating, and a barbecue station.

15. Homewood Suites by Hilton Holyoke-Springfield/North

Holyoke

Andrew

Rp2.627.802

Rp2.935.255 total

includes taxes & fees

4 Oct - 5 Oct

An outdoor seating area with wicker furniture, a fire pit, and decorative lamps.

A conference room with two Dell computers, a large autumn-themed painting, and two wall-mounted lamps.

A hotel room with two beds, a desk with a chair, a TV, and a large window with curtains.

A spacious lobby with a central seating area, a reception desk, and a television screen.

16. Courtyard by Marriott Hadley Amherst

Hadley

Yuki

Rp2.561.919

Rp2.861.664 total

includes taxes & fees

26 Oct - 27 Oct

An outdoor seating area with Adirondack chairs and potted plants.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

17. Cozy Corner Motel

Williamstown

Jonathan

Rp1.579.045

Rp1.856.004 total

includes taxes & fees

27 Sept - 28 Sept

A modern hotel lobby with seating areas, tables, and a reception desk.

A kitchenette with a microwave, coffee maker, and coffee cups.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

18. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Maria Dulce

Rp2.130.457

Rp2.379.720 total

includes taxes & fees

27 Oct - 28 Oct

An indoor swimming pool with clear water, surrounded by windows with a view of trees.

A breakfast area with a sign reading 'HAPPY BREAKFAST STARTS HERE.'

A hotel lobby with a fireplace, seating area, and large windows.

A hotel with a large entrance, a sign reading 'Hampton Inn & Suites,' and a parking lot.

19. Hampton Inn & Suites Greenfield

Greenfield

Pamela

Rp3.802.239

Rp4.247.101 total

includes taxes & fees

12 Oct - 13 Oct

An indoor swimming pool with tiled flooring, metal railings, and multiple seating areas with chairs and tables.

A spacious lobby with a large wooden table, leopard-print chairs, and modern pendant lighting.

A hotel reception area with a central counter, a sign reading "The Pavilion Pantry," and a wall with a quote.

A modern gym with treadmills, an elliptical, and a rowing machine. There are dumbbells and a red exercise ball.

20. Hilton Garden Inn-Springfield, MA

South End

Richard

Rp2.187.389

Rp2.481.593 total

includes taxes & fees

21 Oct - 22 Oct

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Holiday Rentals in Western Massachusetts

Aparthotel

Berkshire Mountain Lodge

Pittsfield

"Clean & comfortable stay"

Aparthotel

Vacation Village in the Berkshires

Williamstown

"Love this place for a weekend getaway."

Aparthotel

A large, multi-story house with a reflective pond in front, surrounded by stone walls and trees.

A stone bench by a calm lake with a stone wall and grass in the foreground.

A serene pond with a stone bridge, surrounded by lush greenery and a house in the background.

The Ponds at Foxhollow

Lenox

"Was a nice place to stay"

Cottage

A cozy room with a large bed, a wooden ceiling, a TV, and a desk with a chair.

A cozy living room with a sofa, armchairs, a coffee table, and a TV. There are wooden walls and a ceiling fan.

A cozy living room with a blue sofa, a coffee table, and a bookshelf.

A garden pathway leading to a porch with a red building, surrounded by various plants and flowers.

Cavalier Cottage B&B

Shelburne Falls

"Cavalier Cottage was perfect for my two-night stay. It was very spacious and clean. Patricia was an excellent host, and provided delicious, warm home-made scones each morning which was a really nice touch!"

Cottage

A spacious living room with a fireplace, a dining area with a wooden table and chairs, and a staircase leading to an upper floor.

A garden with a pond, surrounded by dense foliage and various plants.

A traditional bedroom with a wooden bed, a rocking chair, a chair with a woven seat, and a small table with a lamp.

A hallway with a wooden cabinet and a door leading to a room.

Historic Huntington Home - Walk to Westfield River

Huntington

"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."

Cottage

A wooden deck with outdoor furniture and a red umbrella, overlooking a grassy yard and a forested hill.

A compact kitchen with wooden cabinets, a white refrigerator, a microwave, and a sink.

A white two-story house with a porch, a small attached garage, and a grassy yard.

A living room with a blue sofa, a wooden coffee table, a fan, and a patterned rug.

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Charlemont

"Loved this old home! Record player and records were fun to listen to. Pickle ball across the street was excellent! Well stocked kitchen great for cooking in. I had a tough time with water pressure and temperature but it could have been user error. Beds were comfortable except for the twin, which was a bit too firm! Would definitely rent here again "

Cottage

A spacious living room with exposed wooden beams, a fireplace, and comfortable seating.

A wooden deck with a stone wall, a grill, and outdoor furniture.

A two-story house with a large tree in front, surrounded by lush greenery.

A living room with exposed wooden beams, a television, wicker furniture, and a patterned rug.

Charlemont Retreat on Chickley River w/ EV Charger

Charlemont

"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...

Cottage

A spacious living room with a fireplace, leather sofas, a coffee table, and a dining area with a table and chairs.

A modern kitchen with light grey cabinets, stainless steel appliances, and a large window providing a view of greenery.

A rustic wooden interior with a counter displaying various items, a sign for 'MERLOT', and a view of the outdoors.

A sign for Balderdash Cellars with a wooden fence, a tree, and a parking lot in the background.

3 Acres, Mtn Views, Hot Tub, Steps to Winery

Richmond

"This home is exceptional in all respects --beautifully situated on lovely property, well located in southern Berkshires. Newly remodeled. Great outdoor space. Fabulous kitchen with new appliances, extremely well-outfitted. Host easily accessible. Exceeded all expectations. Would definitely return if plans allow."

Apartment

A lakeside view with a red building, trees, and a calm lake.

A spacious kitchen with a large oven and a dining area with a round table and chairs.

A gazebo with a lattice top and flower arrangements, surrounded by picnic tables and benches, set in a wooded area with a lake in the background.

A compact kitchen with a refrigerator, microwave, and sink. There is a dining table with chairs and a vase of flowers. The room has wooden beams on the ceiling and a ceiling fan.

Lakefront Orange Vacation Rental - Pet Friendly!

Orange

"Lovely, very clean, and well appointed. Host was amazing, 2 rocking chairs on front stoop overlooking the water was beautiful, peaceful.The interiorand decor was beautiful and very comfortable. We used our kayaks, which was great. It is an in̈cline downhill to carry your kayak. "

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Stay near popular Western Massachusetts attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)

Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.

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A roller coaster at an amusement park with a clear sky.

Six Flags New England

8.4/10 (599 reviews)

New England's largest amusement park thrills with 11 roller coasters, including the top-rated Superman The Ride. Experience heart-pounding drops on Wicked Cyclone, or cool off at Hurricane Harbour water park.

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A hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)

Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.

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A basketball court with spectators, a scoreboard, and a wall of portraits.

Naismith Memorial Basketball Hall of Fame

8.6/10 (481 reviews)

The Basketball Hall of Fame celebrates the sport's greatest legends in Springfield, basketball's birthplace. Explore interactive exhibits, test your skills on Centre Court, and immerse yourself in the game's rich history.

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A carousel with colorful decorations and a tall tower structure.

Eastern States Exposition

8.4/10 (260 reviews)

New England's largest fair, The Big E draws 1.6 million visitors annually with agricultural exhibits and entertainment. Explore the Avenue of States and Storrowton Village while sampling diverse regional cuisine.

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A snowy cityscape with various buildings and a large sports stadium.

Amherst College

9.2/10 (300 reviews)

Explore Amherst College's historic College Row and impressive art and natural history museums. Wander through the tranquil Yushien Japanese Garden or attend one of the many public cultural events on campus.

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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)

Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.

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Eastern States Exposition

8.6/10 (302 reviews)

This beloved New England fair showcases all six states' cultures through exhibits, food, and entertainment. Explore the Avenue of States, sample iconic cream puffs, or catch a live concert during its September run.

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Learn more about Western Massachusetts

Rolling hills and charming towns define this picturesque region, where art lovers flock to MASS MoCA in North Adams. Outdoor enthusiasts can hike Mount Greylock, while history buffs explore Norman Rockwell's studio in Stockbridge.

See all hotels in Western Massachusetts

A panoramic view of a valley with autumn foliage, a town in the distance, and rolling hills.

Top Western Massachusetts Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent

"It was very clean and the employees where very friendly"

Hotel UMass

10/10 Excellent

"We didn't expect much from a college hotel. We were wrong. It exceeded our expectations."

Berkshires Untold

10/10 Excellent

"Love the property, room seemed a little tired since I was there last, about 3 years ago. Wish we could stay just one night instead of minimum two, as we often come just for a Tanglewood concert and stay only one night in town."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"I stayed in a townhouse, an upgrade from the room I booked. It was quiet and private, which I enjoyed, and more room than I needed. If my family's schedule had been different, I could have invited them over for a cookout (they live nearby). The townhouse was rather dated and I am afraid a bit dreary, with a lot of browns and beiges. But well-outfitted and convenient."

The Red Lion Inn

10/10 Excellent

"A most amazing place to stay! Has everything a hotel should have - we had a very large room! Great porch! We have stayed there several times."

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."

More cheap stays in Western Massachusetts

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

Rp1.597.843

Rp1.828.731 total

18 Oct - 19 Oct

includes taxes & fees

7.2/10 Good! (1,014 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Rp1.810.888

Rp2.022.761 total

18 Oct - 19 Oct

includes taxes & fees

Holiday Inn Express Springfield Downtown by IHG

145 State Street Springfield MA

Rp1.852.960

Rp2.102.183 total

26 Oct - 27 Oct

includes taxes & fees

Hotel UMass

1 Campus Center Way Amherst MA

Rp1.964.138

Rp2.218.940 total

28 Sept - 29 Sept

includes taxes & fees

9/10 Wonderful! (1,016 reviews)

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA

Rp2.240.739

Rp2.564.527 total

4 Oct - 5 Oct

includes taxes & fees

Comfort Inn & Suites Hadley - Amherst

400 Russell St Hadley MA

Rp2.571.766

Rp2.872.663 total

26 Oct - 27 Oct

includes taxes & fees

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Book Hotels in Western Massachusetts on Expedia.com

Find hotels in Western Massachusetts, MA from Rp1.828.731

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Western Massachusetts

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Western Massachusetts hotels

1. D. Hotel Suites & Spa

2. Comfort Inn & Suites Hadley - Amherst

3. The Yankee Inn

4. Berkshire Mountain Lodge

5. Courtyard by Marriott West Springfield

6. La Quinta Inn & Suites by Wyndham Springfield MA

7. Holiday Inn Express Springfield Downtown by IHG

8. Vacation Village in the Berkshires

9. Tru by Hilton Chicopee Springfield

10. River Valley Inn

11. Maple Terrace Motel

12. Hampton Inn & Suites Springfield/Downtown

13. Hotel Northampton

14. The Inn At Crumpin Fox

15. Homewood Suites by Hilton Holyoke-Springfield/North

16. Courtyard by Marriott Hadley Amherst

17. Cozy Corner Motel

18. Holiday Inn Express Hotel & Suites Great Barrington by IHG

19. Hampton Inn & Suites Greenfield

20. Hilton Garden Inn-Springfield, MA

Holiday Rentals in Western Massachusetts

Berkshire Mountain Lodge

Vacation Village in the Berkshires

The Ponds at Foxhollow

Cavalier Cottage B&B

Historic Huntington Home - Walk to Westfield River

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Charlemont Retreat on Chickley River w/ EV Charger

3 Acres, Mtn Views, Hot Tub, Steps to Winery

Lakefront Orange Vacation Rental - Pet Friendly!

Stay near popular Western Massachusetts attractions

Tanglewood Music Center

Six Flags New England

Jiminy Peak Mountain Resort

Naismith Memorial Basketball Hall of Fame

Eastern States Exposition

Amherst College

Williams College

Eastern States Exposition

Learn more about Western Massachusetts

Top Western Massachusetts Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

Hotel UMass

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Red Lion Inn

Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Western Massachusetts

Quality Inn West Springfield

Quality Inn Great Barrington

Holiday Inn Express Springfield Downtown by IHG

Hotel UMass

Hampton Inn West Springfield

Comfort Inn & Suites Hadley - Amherst

Explore a world of travel with Expedia

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