Search Vacation Homes in Western Massachusetts

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Vacation Homes in Western Massachusetts

Property grounds
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, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
$248 nightly
The price is $277
Dec 8 - Dec 9
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield
10.0 out of 10, Exceptional, (45)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
$181 nightly
The price is $202
Dec 7 - Dec 8
Total with taxes and fees
Lovely 2nd Floor Apartment
Fridge, microwave, oven, stovetop
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Boston Road
9.2 out of 10, Wonderful, (13)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
$283 nightly
The price is $321
Dec 7 - Dec 8
Total with taxes and fees
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Fridge, microwave, oven, stovetop
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Granby
9.4 out of 10, Exceptional, (20)
"Great overnight stay! "
United States
Carrie M.
$255 nightly
The price is $269
Dec 6 - Dec 7
Total with taxes and fees
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Terrace/patio
Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms

Holyoke
9.8 out of 10, Exceptional, (12)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
United States
Eric W.
$288 nightly
The price is $322
Dec 7 - Dec 8
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
$344 nightly
The price is $364
Dec 7 - Dec 8
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$316 nightly
The price is $339
Dec 7 - Dec 8
Total with taxes and fees
Florida Mountain Log Cabin
Dining
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, (10)
"Great stay"
United States
Angelina O.
$283 nightly
The price is $321
Dec 7 - Dec 8
Total with taxes and fees
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.2 out of 10, Wonderful, (24)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
$400 nightly
The price is $446
Dec 8 - Dec 9
Total with taxes and fees
North Getaway Cottage
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$404 nightly
The price is $451
Dec 8 - Dec 9
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop
Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed

Chicopee
10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
United States
Matt G.
$339 nightly
The price is $385
Dec 7 - Dec 8
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
Exterior
Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow

Ludlow
8.4 out of 10, Very Good, (8)
"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."
United States
Matthew H.
$134 nightly
The price is $150
Dec 6 - Dec 7
Total with taxes and fees
Tiny Home with AC and WiFi in lovely Ludlow
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$351 nightly
The price is $392
Dec 15 - Dec 16
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Historic downtown house. Unscented products and sustainability practices.

Historic downtown house. Unscented products and sustainability practices.

Northampton
10.0 out of 10, Exceptional, (6)
"We stayed here to move our daughter into Smith, and it was a great property in a beautiful area. Debra was incredibly responsive and helpful and made a stressful time much easier."
United States
Lindsay R.
$663 nightly
The price is $741
Dec 31 - Jan 1, 2026
Total with taxes and fees
Historic downtown house. Unscented products and sustainability practices.
Fridge, microwave, oven, stovetop
Beautiful 4BR 2 Bathroom House with Parking

Beautiful 4BR 2 Bathroom House with Parking

Forest Park
10.0 out of 10, Exceptional, (11)
"Arranged for my managers to stay at this location as they needed to be close to a Trade Show. Host was very accommodating and quick with responses. Everyone who stayed at the house was more than pleased with everything!"
United States
Ursula D.
$686 nightly
The price is $778
Dec 6 - Dec 7
Total with taxes and fees
Beautiful 4BR 2 Bathroom House with Parking
Smart TV, fireplace, video games, books
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Forest Park
9.8 out of 10, Exceptional, (36)
"His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
$272 nightly
The price is $308
Dec 6 - Dec 7
Total with taxes and fees
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Dec 8 - Dec 9
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Smart TV
PICON COZY

PICON COZY

Sixteen Acres
7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
United States
Linda W.
$151 nightly
The price is $171
Dec 23 - Dec 24
Total with taxes and fees
PICON COZY
Dining
FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain
9.8 out of 10, Exceptional, (38)
"Great place and convenient to get to and from Berkshire East."
United States
Jeffrey B.
$573 nightly
The price is $640
Dec 7 - Dec 8
Total with taxes and fees
FaLL Western Mass Getaway-Airhockey-Firepit
Property grounds
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge
10.0 out of 10, Exceptional, (29)
"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "
United States
Phillip F.
$764 nightly
The price is $853
Dec 7 - Dec 8
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the many nature trails here. And the bed was so perfectly firm and cozy that I drifted effortlessly to sleep. The grounds, the amenities and the coordinated activities to bring you together in community made me feel included. Definitely a place I will continue to return to for many years."
salena 9-night trip
Posted 1 day ago
Berkshire Mountain Lodge

Find out more about Western Massachusetts

Western Massachusetts Vacation Homes information

Number of reviews
596
Accommodation
446 Vacation Homes
Lowest Price
$150
Highest Price
$853

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