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Our top choices for Western Massachusetts vacation homes

1. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 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 ¥39,392
¥63,414 total
includes taxes & fees
Dec 6 - Dec 7
Charming, updated 3 bedroom farmhouse farm stay.

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 ¥28,748
¥42,459 total
includes taxes & fees
Nov 18 - Nov 19
The Creation Station is a cozy place so make yourself at home.

3. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (74 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is ¥24,436
¥37,999 total
includes taxes & fees
Nov 17 - Nov 18
Lovely 2nd Floor Apartment

4. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is ¥18,367
¥31,577 total
includes taxes & fees
Nov 16 - Nov 17
Private room with En-suite bathroom Marigold Room

5. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is ¥23,637
¥53,519 total
includes taxes & fees
Nov 27 - Nov 28
Cozy Home in Holyoke with 3 bedrooms

6. 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, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ¥25,586
¥57,657 total
includes taxes & fees
Nov 16 - Nov 17
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

7. 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, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is ¥23,286
¥57,408 total
includes taxes & fees
Nov 16 - Nov 17
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 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 ¥12,457
¥49,058 total
includes taxes & fees
Nov 26 - Nov 27
Real Estate: Therapy - Lake, Laundry, Love it

9. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
10.0 out of 10, Exceptional, (1 review)
"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 ¥32,142
¥63,199 total
includes taxes & fees
Nov 16 - Nov 17
Shelburne Falls on Main

10. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (44 reviews)
"Clean, comfortable, peaceful, great hosts!"
United States
Megan D.
The price is ¥34,967
¥63,295 total
includes taxes & fees
Dec 3 - Dec 4
Linny's - Private Dock - Lake Access - Firepit

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (20 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is ¥31,910
¥66,280 total
includes taxes & fees
Nov 16 - Nov 17
Townhouse with Pool Table - Renovated w/ King Bed

12. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
West Springfield
10.0 out of 10, Exceptional, (1 review)
"Adorable home, set up so cute plus being pet friendly means everything to me when deciding. All was as described and our host had everything you could need and more available to us in the well stocked kitchen and bathroom. Very quiet safe and friendly neighborhood on a dead end street, gated walkway as well as a gated driveway made me feel plenty safe enough to take my dog out at night. Bedrooms were welcoming and set up with pretty fairy lights throughout, all three beds were very comfortable...
United States
Jaimie F.
The price is ¥22,998
¥46,793 total
includes taxes & fees
Nov 16 - Nov 17
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

13. Bling nest

Bling nest
Ludlow
The price is ¥28,748
¥63,509 total
includes taxes & fees
Nov 16 - Nov 17
Bling nest

14. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (156 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 ¥31,623
¥55,203 total
includes taxes & fees
Nov 18 - Nov 19
Big farmhouse in the foothills of the Berkshires

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

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.8 out of 10, Excellent, (26 reviews)
"The stove was broken, which we were made aware of and there was an offer to cancel for us. We chose to still go because we needed a place to stay. The stove was in the middle of the kitchen when we arrived. I did decide to cancel the second night in the owner, said they would refund us, but they only refund part of the second night."
United States
Gladys B.
The price is ¥28,748
¥59,614 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

16. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (54 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 ¥27,454
¥53,073 total
includes taxes & fees
Nov 16 - Nov 17
Cozy & Spacious Entire Home in Springfield

17. 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 ¥43,122
¥87,295 total
includes taxes & fees
Nov 30 - Dec 1
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

18. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ¥31,942
¥48,346 total
includes taxes & fees
Dec 13 - Dec 14
Home in Great Barrington

19. 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 ¥39,482
¥77,105 total
includes taxes & fees
Dec 4 - Dec 5
A roomy remodeled retreat close to MassMoCA

20. 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 ¥28,029
¥53,725 total
includes taxes & fees
Nov 16 - Nov 17
Beautifully Renovated First-Floor Apartment Getaway
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.

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.

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

Top reviews in Western Massachusetts

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