A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Western Massachusetts vacation homes

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

1. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 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 ￥19,778
￥33,748 total
includes taxes & fees
Oct 18 - Oct 19
Lovely 2nd Floor Apartment
A cozy room with two beds, large windows, and a view of a snowy landscape.

2. 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 ￥28,458
￥43,797 total
includes taxes & fees
Nov 3 - Nov 4
The Creation Station is a cozy place so make yourself at home.
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

3. 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 ￥42,687
￥69,686 total
includes taxes & fees
Oct 18 - Oct 19
Charming, updated 3 bedroom farmhouse farm stay.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

4. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥18,972
￥33,906 total
includes taxes & fees
Oct 20 - Oct 21
Private bed with En-suite bathroom Marigold Room
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.

5. 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 ￥23,051
￥59,302 total
includes taxes & fees
Oct 27 - Oct 28
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use 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.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 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 ￥11,699
￥50,329 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
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
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,328
￥62,197 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A bedroom with a bed, a desk, a chair, a ceiling fan, a window with curtains, and a wall-mounted TV.

8. 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 ￥33,296
￥70,957 total
includes taxes & fees
Oct 27 - Oct 28
Townhouse with Pool Table - Renovated w/ King Bed
A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

9. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"Fantastic stay in Holyoke. House is close to town, well outfitted, and super clean. Easy check in process and great experience all around. "
United States
Grant J.
The price is ￥24,664
￥57,041 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Home in Holyoke with 3 bedrooms
A house with a porch, a garden with pink flowers, and a stone wall along the road.

10. 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 place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is ￥31,304
￥57,152 total
includes taxes & fees
Oct 19 - Oct 20
Big farmhouse in the foothills of the Berkshires
A hallway with wooden flooring, white walls, and a bed in the background.

11. 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 ￥33,201
￥67,638 total
includes taxes & fees
Oct 19 - Oct 20
Cozy private 2 bed apartment in Shelburne Falls
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 ￥26,324
￥53,901 total
includes taxes & fees
Oct 18 - Oct 19
Cozy & Spacious Entire Home in Springfield
A dining area with a round table, four chairs, and a kitchen in the background.

13. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is ￥28,316
￥39,301 total
includes taxes & fees
Oct 19 - Oct 20
Cozy 2-Bedroom Springfield Home 1.5 Baths
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

14. 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, (22 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 ￥28,458
￥61,702 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
A bedroom with a four-poster bed, a dresser, a chair, and a large window.

15. Steps from Amherst town common, 3 BR charmer

Steps from Amherst town common, 3 BR charmer
East Village Historic District
The price is ￥39,051
￥49,977 total
includes taxes & fees
Nov 4 - Nov 5
Steps from Amherst town common, 3 BR charmer
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

16. 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 ￥36,426
￥56,581 total
includes taxes & fees
Oct 26 - Oct 27
Home in Great Barrington
A living room with two sofas, a coffee table, and a potted plant.

17. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.2 out of 10, Wonderful, (13 reviews)
"Great stay"
United States
Angelina O.
The price is ￥28,454
￥61,693 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

18. Amherst -NEW - Campus Convenience & Social Privacy

Amherst -NEW - Campus Convenience & Social Privacy
Amherst
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our stay!"
United States
Susan N.
The price is ￥94,702
￥119,380 total
includes taxes & fees
Nov 5 - Nov 6
Amherst -NEW - Campus Convenience & Social Privacy
A modern living room with a black leather sofa set, a glass coffee table, and a patterned rug.

19. Beautifully Renovated First-Floor Apartment Getaway

Beautifully Renovated First-Floor Apartment Getaway
Forest Park
9.6 out of 10, Exceptional, (7 reviews)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is ￥28,173
￥52,231 total
includes taxes & fees
Oct 27 - Oct 28
Beautifully Renovated First-Floor Apartment Getaway
A dining area with a long wooden table set for six, surrounded by chairs. There are hanging pendant lights above the table.

20. Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Amherst
10.0 out of 10, Exceptional, (13 reviews)
"Perfect location, clean house, great for families with kids!"
United States
Emily Robustelli K.
The price is ￥157,942
￥256,951 total
includes taxes & fees
Nov 4 - Nov 5
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
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.
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Top Western Massachusetts Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Great room and great bar. It takes time but is worth it"
Benjamin 1-night trip
Posted 1 hour ago
Berkshires Untold

Find out more about Western Massachusetts

Western Massachusetts Vacation Homes information

Number of reviews
533
Accommodation
472 Vacation Homes
Lowest Price
￥33,748
Highest Price
￥256,951

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