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26 Sep - 28 Sep
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Vacation Homes in Western Massachusetts

Our top choices for Western Massachusetts vacation homes

Tiny Home with AC and WiFi in lovely Ludlow
1 bedroom, WiFi, bed sheets

Tiny Home with AC and WiFi in lovely Ludlow

9.0 out of 10, Wonderful, (6)
The price is SAR 296
SAR 562 total
includes taxes & fees
29 Sep - 30 Sep
Tiny Home with AC and WiFi in lovely Ludlow
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (147)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Fridge, microwave, oven, stovetop

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

10.0 out of 10, Exceptional, (23)
"This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. "
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Spacious Private Retreat Near Holyoke State Park!
Fridge, microwave, oven, stovetop

Spacious Private Retreat Near Holyoke State Park!

9.4 out of 10, Exceptional, (10)
"Enjoyed our stay. Plenty of room for our family of 10! Host very nice to work with! "
Spacious Private Retreat Near Holyoke State Park!
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

10.0 out of 10, Exceptional, (37)
"We had the most wonderful trip! The location is perfect - easy access to downtown GB but still very relaxing and private. The kitchen is beautifully equipped and we ended up cooking most of our meals there. And the living room/great room led to hours of conversation. Can't wait to come back for a longer stay."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Smart TV, fireplace, video games, books

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

9.6 out of 10, Exceptional, (35)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is SAR 694
SAR 1,158 total
includes taxes & fees
1 Oct - 2 Oct
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Fireplace, books

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

9.6 out of 10, Exceptional, (37)
"My friends and I had the most beautiful rainy weekend here to celebrate my 40th birthday. The spot was perfect for the 5 of us and the river was such a wonderful bonus to our peaceful trip!"
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (11)
"I was in a nice, quiet neighborhood. House was clean and comfy. There is a store literally right around the corner. I would definitely stay agin and recommend to others. The property manager answered my questions and gave good customer service."
The price is SAR 525
SAR 1,281 total
includes taxes & fees
15 Sep - 16 Sep
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (36)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is SAR 436
SAR 759 total
includes taxes & fees
14 Sep - 15 Sep
Lovely 2nd Floor Apartment
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (73)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (48)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
General Williams Estate House Lenox/Stockbridge
Exterior

General Williams Estate House Lenox/Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (110)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
General Williams Estate House Lenox/Stockbridge
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

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

10.0 out of 10, Exceptional, (25)
"We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior detail

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (93)
"This was our third time at this property. We still love it and look forward to returning again."
Hearts Desire is a furnished whole house in a small, colorful garden center.
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Amazing Inn. Cozy and everything we needed. "
The price is SAR 2,247
SAR 4,168 total
includes taxes & fees
17 Sep - 18 Sep
Hancock Village Inn at Jiminy Peak
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is SAR 1,097
SAR 2,307 total
includes taxes & fees
18 Sep - 19 Sep
Spacious 5-bedroom house in charming Lee with WiFi
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is SAR 604
SAR 1,776 total
includes taxes & fees
13 Sep - 14 Sep
Comfortable Berkshires retreat on mtn resort, SISO
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (220)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake
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, (7)
"We had a wonderful four night stay at this home in Williamstown. Kathy, the owner, was great and easy to reach. The home was thoughtfully and thoroughly appointed, comfortably accommodating our extended family of ten. The grounds were beautifully maintained and the views of the Berkshires were breathtaking. We wouldn’t hesitate to stay again and we would highly recommend this lovely property. "
Contemporary Berkshire Home with Views of Taconic Golf Course
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"I visit here vacation village every 2 to 3 months. It's a wonderful experience. Peaceful and safe. Staff are friendly and very helpful. A beautiful outdoor heated swimming pool with Jacuzzi. Its a beautiful Place to visit. I would highly recommend it. "
Claire 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires

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