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Our top choices for Western Massachusetts vacation homes

1. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is AED 562
AED 874 total
includes taxes & fees
5 Nov - 6 Nov
Lovely 2nd Floor Apartment

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 AED 661
AED 972 total
includes taxes & fees
5 Nov - 6 Nov
The Creation Station is a cozy place so make yourself at home.

3. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 422
AED 726 total
includes taxes & fees
8 Nov - 9 Nov
Private room with En-suite bathroom Marigold Room

4. 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 AED 1,037
AED 1,601 total
includes taxes & fees
5 Nov - 6 Nov
Charming, updated 3 bedroom farmhouse farm stay.

5. 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 AED 195
AED 1,018 total
includes taxes & fees
9 Nov - 10 Nov
Real Estate: Therapy - Lake, Laundry, Love it

6. 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 AED 569
AED 1,260 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Home in Holyoke with 3 bedrooms

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 AED 536
AED 1,312 total
includes taxes & fees
5 Nov - 6 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (18 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AED 747
AED 1,543 total
includes taxes & fees
9 Nov - 10 Nov
Townhouse with Pool Table - Renovated w/ King Bed

9. Bling nest

Bling nest
Ludlow
The price is AED 661
AED 1,473 total
includes taxes & fees
5 Nov - 6 Nov
Bling nest

10. 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 AED 739
AED 1,453 total
includes taxes & fees
5 Nov - 6 Nov
Shelburne Falls on Main

11. 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 AED 588
AED 1,375 total
includes taxes & fees
5 Nov - 6 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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 AED 595
AED 1,160 total
includes taxes & fees
9 Nov - 10 Nov
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

13. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is AED 658
AED 880 total
includes taxes & fees
5 Nov - 6 Nov
Cozy 2-Bedroom Springfield Home 1.5 Baths

14. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (155 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 AED 727
AED 1,270 total
includes taxes & fees
5 Nov - 6 Nov
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, (25 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 AED 661
AED 1,371 total
includes taxes & fees
5 Nov - 6 Nov
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

16. 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 AED 992
AED 1,995 total
includes taxes & fees
22 Nov - 23 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

17. 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 AED 612
AED 1,198 total
includes taxes & fees
5 Nov - 6 Nov
Beautifully Renovated First-Floor Apartment Getaway

18. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AED 793
AED 1,186 total
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington

19. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (53 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 AED 661
AED 1,208 total
includes taxes & fees
8 Nov - 9 Nov
Cozy & Spacious Entire Home in Springfield

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

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.0 out of 10, Wonderful, (14 reviews)
"Our stay was fantastic. Check in was super smooth and the host was very responsive. I would definitely stay here again in the future."
United States
Nicholas T.
The price is AED 661
AED 1,371 total
includes taxes & fees
5 Nov - 6 Nov
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
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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