Holiday Homes in Western Massachusetts

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Western Massachusetts

Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is AU$312
includes taxes & fees
19 Aug - 20 Aug
Lovely 2nd Floor Apartment
Contemporary Berkshire Home with Views of Taconic Golf Course
Smart TV, fireplace, DVD player, books

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (128)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Terrace/patio

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (107)
"My wife and I stayed in the upper apartment for 2 nights. The place was perfect in every aspect. It was clean, quiet and well equipped. Beds were comfortable and it was close the UMASS. We will definitely stay here again when we are in the area. "
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Tiny Home with AC and WiFi in lovely Ludlow
1 bedroom, WiFi, bed sheets

Tiny Home with AC and WiFi in lovely Ludlow

8.6 out of 10, Excellent, (4)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
The price is AU$233
includes taxes & fees
18 Aug - 19 Aug
Tiny Home with AC and WiFi in lovely Ludlow
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds
Property grounds

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (4)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is AU$207
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds
3-bedroom house in perfect Springfield with WiFi, AC
TV

3-bedroom house in perfect Springfield with WiFi, AC

2.0 star property
9.2 out of 10, Wonderful, (5)
3-bedroom house in perfect Springfield with WiFi, AC
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is AU$565
includes taxes & fees
18 Aug - 19 Aug
Big farmhouse in the foothills of the Berkshires
Lake Congamond Cozy Stylish Comfortable House
Sun-loungers, beach towels

Lake Congamond Cozy Stylish Comfortable House

2.0 star property
10.0 out of 10, Exceptional, (6)
"This cozy cottage was perfect. It was definitely a great lication and close to a lot of stores. The beds were really comfortable too. Thesellerr was super helpfula sn"
Lake Congamond Cozy Stylish Comfortable House
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Exterior

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (13)
"The place was very comfortable and in a great location. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Spacious Private Retreat Near Holyoke State Park!
Fridge, microwave, oven, stovetop

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (9)
"We stayed for a guys hunting trip and the place was what we needed after a long day"
Spacious Private Retreat Near Holyoke State Park!
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (5)
"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.
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Dining

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (3)
"Friends and I were in the area for a concert at Tree House Brewing. This house wasn’t far and it is a gorgeous home. Super clean and had all amenities. Would stay here again!"
The price is AU$578
includes taxes & fees
21 Aug - 22 Aug
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Poolside Luxe at Long Pond
Exterior

Poolside Luxe at Long Pond

Poolside Luxe at Long Pond
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (130)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Home in the woods - Big, Acreage, Nature Oasis, King Bed, Giant Windows
Exterior

Home in the woods - Big, Acreage, Nature Oasis, King Bed, Giant Windows

9.4 out of 10, Exceptional, (28)
"Very Large home with well equipped kitchen. Beds were all very comfortable. Host was very attentive to our needs and questions during our stay."
Home in the woods - Big, Acreage, Nature Oasis, King Bed, Giant Windows
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Private kitchen

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

9.0 out of 10, Wonderful, (2)
"Mini family vacation. The property was pleasant and convenient to the Museums and Zoo.This is not specific to this stay, but I wish the fees would be available prior to the booking/ payment process. We had to stop the booking of a different property for this trip when the hidden fees more than doubled the cost of the rental."
The price is AU$560
includes taxes & fees
26 Aug - 27 Aug
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Fridge, microwave, oven, stovetop

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (81)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
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 Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Walking distance to MassMOCA and several good restaurants and coffee shops. "
James 2-night trip
Posted 1 day ago
Hotel Downstreet, Ascend Hotel Collection