A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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, (71 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 AED 562
AED 919 total
includes taxes & fees
27 Oct - 28 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 1,030 total
includes taxes & fees
3 Nov - 4 Nov
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, (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 992
AED 1,631 total
includes taxes & fees
8 Nov - 9 Nov
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 room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 473
AED 824 total
includes taxes & fees
9 Nov - 10 Nov
Private room 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, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,378 total
includes taxes & fees
3 Nov - 4 Nov
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 AED 217
AED 1,100 total
includes taxes & fees
28 Oct - 29 Oct
Real Estate: Therapy - Lake, Laundry, Love it
A bedroom with a bed, curtains, a bedside table, and a lamp.

7. 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 904
AED 1,817 total
includes taxes & fees
25 Nov - 26 Nov
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.

8. 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 577
AED 1,329 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Home in Holyoke with 3 bedrooms
A hot tub with a string of lights above it, set against a dark night sky.

9. 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 AED 588
AED 1,445 total
includes taxes & fees
9 Nov - 10 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A hallway with wooden flooring, white walls, and a bed in the background.

10. Shelburne Falls on Main

Shelburne Falls on Main
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 739
AED 1,531 total
includes taxes & fees
8 Nov - 9 Nov
Shelburne Falls on Main
A house with a porch, a garden with pink flowers, and a stone wall along the road.

11. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (154 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 1,328 total
includes taxes & fees
27 Oct - 28 Oct
Big farmhouse in the foothills of the Berkshires
A single-story house with a red front door, white siding, and a brick chimney.

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
The price is AED 661
AED 1,341 total
includes taxes & fees
27 Oct - 28 Oct
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

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 913 total
includes taxes & fees
27 Oct - 28 Oct
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
8.8 out of 10, Excellent, (23 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 1,446 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
A modern living room with a sofa, a coffee table, and a red patterned rug.

15. 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 612
AED 1,261 total
includes taxes & fees
29 Oct - 30 Oct
Cozy & Spacious Entire Home in Springfield
A two-story house with a front porch, a small entryway, and a set of stairs leading to the front door.

16. Bling nest

Bling nest
Ludlow
The price is AED 826
AED 1,760 total
includes taxes & fees
27 Oct - 28 Oct
Bling nest
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

17. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AED 846
AED 1,314 total
includes taxes & fees
27 Oct - 28 Oct
Home in Great Barrington
A kitchen with white cabinets, a wooden dining table, and pendant lights.

18. 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 AED 841
AED 1,768 total
includes taxes & fees
30 Oct - 31 Oct
A roomy remodeled retreat close to MassMoCA
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 AED 612
AED 1,265 total
includes taxes & fees
2 Nov - 3 Nov
Beautifully Renovated First-Floor Apartment Getaway
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

20. Amherst -NEW - Campus Convenience & Social Privacy

Amherst -NEW - Campus Convenience & Social Privacy
Amherst
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic property and host. Left a suit accidentally and they were extremely accommodating in helping us get it back."
United States
Kimberly D.
Amherst -NEW - Campus Convenience & Social Privacy
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

Hotel On North

Hotel On North

10/10 Excellent
"Perfect for our weekend family trip. Staff was super friendly. Walkable to multiple bakeries/cafes for breakfast. Walls are a little thin so noise can be a problem but otherwise no complaints."
Rahul 3-night trip
Posted less than an hour ago
Hotel On North

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