A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (69 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is AED 511
AED 853 total
includes taxes & fees
22 Oct - 23 Oct
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 AED 661
AED 1,017 total
includes taxes & fees
20 Oct - 21 Oct
The Creation Station is a cozy place so make yourself at home.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

3. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 780 total
includes taxes & fees
28 Oct - 29 Oct
Private bed with En-suite bathroom Marigold Room
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

4. 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 AED 992
AED 1,631 total
includes taxes & fees
5 Oct - 6 Oct
Charming, updated 3 bedroom farmhouse farm stay.
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 AED 542
AED 1,385 total
includes taxes & fees
7 Oct - 8 Oct
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
9.0 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 AED 345
AED 1,251 total
includes taxes & fees
28 Oct - 29 Oct
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
9.8 out of 10, Exceptional, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 588
AED 1,441 total
includes taxes & fees
14 Oct - 15 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A bedroom with a bed, curtains, a bedside table, and a lamp.

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 AED 803
AED 1,686 total
includes taxes & fees
5 Oct - 6 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.

9. 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 AED 680
AED 1,270 total
includes taxes & fees
12 Oct - 13 Oct
Big farmhouse in the foothills of the Berkshires
A hallway with wooden flooring, white walls, and a bed in the background.

10. 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 AED 771
AED 1,571 total
includes taxes & fees
5 Oct - 6 Oct
Cozy private 2 bed apartment in Shelburne Falls
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

11. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 779
AED 1,231 total
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A bedroom with a bed, dresser, and floor lamp.

12. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is AED 658
AED 913 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 2-Bedroom Springfield Home 1.5 Baths
A modern living room with a sofa, a coffee table, and a red patterned rug.

13. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (50 reviews)
"It was nice stay!"
United States
Lorrie
The price is AED 615
AED 1,256 total
includes taxes & fees
11 Oct - 12 Oct
Cozy & Spacious Entire Home in Springfield
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, (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 AED 661
AED 1,433 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Pool

15. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is AED 591
AED 1,988 total
includes taxes & fees
27 Oct - 28 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A living room with two sofas, a coffee table, and a potted plant.

16. 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 AED 661
AED 1,433 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
A modern living room with a black leather sofa set, a glass coffee table, and a patterned rug.

17. Beautifully Renovated First-Floor Apartment Getaway

Beautifully Renovated First-Floor Apartment Getaway
Forest Park
9.4 out of 10, Exceptional, (6 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 618
AED 1,168 total
includes taxes & fees
12 Oct - 13 Oct
Beautifully Renovated First-Floor Apartment Getaway
A two-story house with a porch, a large tree in front, and a mailbox.

18. Modern Victorian 3BR 2BA Apt with Parking

Modern Victorian 3BR 2BA Apt with Parking
McKnight
10.0 out of 10, Exceptional, (3 reviews)
"This is a beautiful old Victorian home. Very well maintained and very well appointed. The hosts are attentive and respond to questions promptly. The house was well stocked with all essentials Highly recommended."
United States
Brandi S.
The price is AED 1,469
AED 2,654 total
includes taxes & fees
7 Oct - 8 Oct
Modern Victorian 3BR 2BA Apt with Parking
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

19. 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.
Greylock Cabin
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

20. 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 1,116
AED 2,273 total
includes taxes & fees
4 Nov - 5 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"The personal was excellent"
Vielka 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA

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