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Compare 348 Vacation Homes in Western Massachusetts with updated reviews, rates, and availability.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AED 962
AED 1,962 total
includes taxes & fees
6 Nov - 7 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Historic Farmhouse Near Mountains & Colleges!
Westfield Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required
Historic Farmhouse Near Mountains & Colleges!
10.0 out of 10, Exceptional, (2)
"Beautiful & well-maintained historic home.... everything was perfect! Amendies were first class! We will be back:)"
Historic Farmhouse Near Mountains & Colleges!
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!
Amore Estate - beautiful room with many places to explore and relax in.
9.8 out of 10, Exceptional, (16)
"Clean, house has plenty of room. Lovely property. "
Amore Estate - beautiful room with many places to explore and relax in.
Secluded Family Home in Serene Stockbridge Woods
Living area
Secluded Family Home in Serene Stockbridge Woods
10.0 out of 10, Exceptional, (18)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Spectacular views and close to Great Barrington.
Private kitchen
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (220)
"A quick weekend! Repeat guests! Place is always immaculate- and easy check in/check out. "
The price is AED 525
AED 808 total
includes taxes & fees
11 Nov - 12 Nov
Berkshire Village Carriage House - Super Private!!
PICON COZY
Private kitchen
PICON COZY
8.0 out of 10, Very Good, (50)
"Had a good weekend at the property, it worked for what i intended it to do. Hopefully will be able to return again next year."
The price is AED 275
AED 625 total
includes taxes & fees
6 Nov - 7 Nov
PICON COZY
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Fully stocked newly renovated Kitchen.
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (105)
"Julie was a fantastic host. She was proactive in reaching out to ensure there were no issues with our stay. The property was everything the listing had described. We enjoyed our stay and the area. It was a good point to get to the places we wanted to see. "
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Charming 4Bds+1crib house with patio Amherst Center
Pool
Charming 4Bds+1crib house with patio Amherst Center
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location near restaurants and stores. House is "
The price is AED 716
AED 1,493 total
includes taxes & fees
6 Nov - 7 Nov
Charming 4Bds+1crib house with patio Amherst Center
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
View from deck looking over our dock on a still day in last days of October.
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (145)
"Beautiful fall colors surrounding the lake. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Tranquil 3-BR Waterfront Retreat
Tranquil 3-BR Waterfront Retreat
9.8 out of 10, Exceptional, (10)
"Very clean and nicely decorated. Comfortable vibe. Came to relax and enjoy the fall colors. It looks bigger in the pictures, but was plenty big for the 4 of us. Having laundry was a plus, and enjoyed the ping pong table Loved the duvet covers…so soft. Upstairs bathroom could use a mirror in a better place, as blow drying hair and putting on makeup would be difficult, but just didn’t bother. Hope to go again next fall. "
Tranquil 3-BR Waterfront Retreat
The Creation Station is a cozy place so make yourself at home.
Exterior
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (61)
"We needed a pet friendly location to stay for one night. This place is amazing. Very unconventional and much more than I needed for my family of four but I would recommend it highly. The host was very helpful and friendly. The property would be great for an adult birthday or an extended family get together. "
The price is AED 661
AED 1,034 total
includes taxes & fees
13 Nov - 14 Nov
The Creation Station is a cozy place so make yourself at home.
Amherst, Perfect Location, UMass, Smith, MHC!
The Valley is known for our picturesque red tobacco barns and expansive cornfields.
Amherst, Perfect Location, UMass, Smith, MHC!
10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lenox Vacation Rental | 3BR | 2BA | 2,457 Sq Ft | Step-Free Access
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (35)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Great Room with lake view
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
10.0 out of 10, Exceptional, (89)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
Granby Vacation Rental | 3BR | 2.5BA | 3,300 Sq Ft | 4 Stairs to Access
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
9.8 out of 10, Exceptional, (27)
"Very quiet home. Well equipped for a large family "
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Front of house
1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, (67)
"The house was clean and looked newly remodeled. It had everything we needed for our 3 night stay. It is a good location when visiting Western MA. We would stay there again. Western MA. "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Exterior
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
10.0 out of 10, Exceptional, (31)
"The castle house is fantastic. Spacious, beautifully decorated and equipped. There is no meal you can't craft from this kitchen. The house is super quiet,the beds are comfy, towels plush...close to Great Barrington. I can't say enough good things. Book it."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Lovely 2nd Floor Apartment
Living area
Lovely 2nd Floor Apartment
9.8 out of 10, Exceptional, (12)
"Apartment was clean and a good location for what I needed. Everything required for a comfortable stay"
The price is AED 437
AED 763 total
includes taxes & fees
6 Nov - 7 Nov
Lovely 2nd Floor Apartment
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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Other property types in Western Massachusetts

Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1743)
"The suite was clean, comfortable, and ready when I arrived."
The price is AED 620
AED 717 total
includes taxes & fees
6 Nov - 7 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (914)
"Nice fall view"
The price is AED 547
AED 600 total
includes taxes & fees
6 Nov - 7 Nov
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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.