A lake with a rocky shoreline and a forested island.

Holiday Homes in Western Massachusetts

  • 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

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Western Massachusetts holiday homes

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

1. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is NZ$766
includes taxes & fees
11 Oct - 12 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

2. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is NZ$404
includes taxes & fees
2 Nov - 3 Nov
Lovely 2nd Floor Apartment
A cozy room with two beds, large windows, and a view of a snowy landscape.

3. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is NZ$495
includes taxes & fees
12 Oct - 13 Oct
The Creation Station is a cozy place so make yourself at home.
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

4. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$657
includes taxes & fees
14 Oct - 15 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A bedroom with a bed, curtains, a bedside table, and a lamp.

5. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is NZ$798
includes taxes & fees
13 Oct - 14 Oct
Townhouse with Pool Table - Renovated w/ King Bed
A house with a porch, a garden with pink flowers, and a stone wall along the road.

6. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (153 reviews)
"Great location"
United States
Will G.
The price is NZ$619
includes taxes & fees
12 Oct - 13 Oct
Big farmhouse in the foothills of the Berkshires
A hot tub with a string of lights above it, set against a dark night sky.

7. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$677
includes taxes & fees
12 Oct - 13 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

8. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is NZ$861
includes taxes & fees
31 Oct - 1 Nov
Greylock Cabin
A kitchen with white cabinets, a wooden dining table, and pendant lights.

9. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is NZ$839
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

10. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is NZ$617
includes taxes & fees
13 Oct - 14 Oct
Home in Great Barrington
A lakeside residential area with houses along the water's edge, a dock, and a boat.

11. 3br Lakefront Oasis in Shutesbury with central air and 180-deg views!

3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
Shutesbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time at the house. Perfect for family and young kids. Very clean. View of lake and bald eagles! were amazing. Host was very responsive and provided a lot of extra info on location places to eat, events, etc. Would definitely stay again."
United States
Tara I.
The price is NZ$1,372
includes taxes & fees
1 Nov - 2 Nov
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
A modern living room with a sofa, a coffee table, and a red patterned rug.

12. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (51 reviews)
"House was super clean, coffee was a nice surprise. Comfy beds, quiet street. Super close to the Big E. Thanks Rose!"
United States
Brian
The price is NZ$611
includes taxes & fees
12 Oct - 13 Oct
Cozy & Spacious Entire Home in Springfield
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

13. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is NZ$1,065
includes taxes & fees
13 Oct - 14 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

14. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is NZ$1,150
includes taxes & fees
13 Oct - 14 Oct
Spacious 5BR w/ Hot Tub & Games
A staircase with a wooden handrail and a white wall with a light switch.

15. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is NZ$530
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

16. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is NZ$588
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A hallway with wooden flooring, white walls, and a bed in the background.

17. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is NZ$760
includes taxes & fees
19 Oct - 20 Oct
Cozy private 2 bed apartment in Shelburne Falls
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

18. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is NZ$1,356
includes taxes & fees
13 Oct - 14 Oct
5BR Berkshire Home Mins To The Mountain
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

19. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.6 out of 10, Excellent, (21 reviews)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is NZ$703
includes taxes & fees
18 Oct - 19 Oct
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

20. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (29 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
Secluded Family Home in Serene Stockbridge Woods
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Western Massachusetts Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

8/10 Good
"Clean, friendly with decent bar and good choices available in their lobby store for food and drinks."
Adam 2-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Springfield MA

Find out more about Western Massachusetts

Western Massachusetts Holiday Homes information

Number of reviews
684
Accommodation
464 Holiday Homes
Lowest Price
NZ$404
Highest Price
NZ$1,372

Explore a world of travel with Expedia