Holiday Rentals in Western Massachusetts

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Holiday Rentals in Western Massachusetts

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1762)
"In door pool was very nice. Room was clean and had all the basics. "
The price is €130
includes taxes & fees
23 Feb - 24 Feb
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is €198
includes taxes & fees
23 Feb - 24 Feb
Jiminy Peak Mountain Resort

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (16)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
The price is €2,540
includes taxes & fees
19 Feb - 20 Feb
Private Estate, Heated Yearround Outdoor Pool

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

PICON COZY

7.6 out of 10, Good, (57)
"I booked this for my elderly Mom and her adult granddaughter who were in town for the holidays and also awaiting a January 1 move in to a new apartment. Fidelis was attentive, kind, and responded quickly to any issues in the property. The place itself was truly like home away from home and convenient to stores, shopping and public transportation. I would recommend anyone looking for a cozy stay in Springfield to check it out. It is well worth the price. I would even say it is a bargain and...
The price is €167
includes taxes & fees
18 Feb - 19 Feb
PICON COZY

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

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is €1,070
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at Jiminy Peak

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (55)
"Perfect lake front home to get away for a quick weekend trip with the family over the holidays!! Location, location location, close proximity to downtown Pittsfield, 15 from Jiminy peak & Bousquet Mt. Andrey was extremely helpful throughout the process with suggestions for food and activities for the kids. The house was a perfect fit for our family and friends. Everyone enjoyed their time there and would definitely book again"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

Peaceful Retreat Compound 10 Minutes to Great Barrington!

10.0 out of 10, Exceptional, (22)
"This home is located in a beautiful area with plenty of nature surrounding. The amenities included are incredible. A large group of us visited and had so much fun on the pickle ball courts, hanging around the bonfire, and relaxing with the sauna and hot tub. This place can’t be beat!!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!

Comfortable Berkshires retreat on mtn resort, SISO

The price is €660
includes taxes & fees
24 Feb - 25 Feb
Comfortable Berkshires retreat on mtn resort, SISO

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (43)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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

9.6 out of 10, Exceptional, (30)
"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 €304
includes taxes & fees
7 Mar - 8 Mar
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (40)
"We have stayed here twice and it is a great spot, located a few minute drive north of downtown Lenox. The house is cozy yet spacious and is great for our family to stay in while visiting family in the area. We used the kitchen to cook a meal during one of the stays and we had everything we needed. There is an air hockey table in the basement which the kids enjoyed. The house is on a main road, but it was still easy enough to pull in and out of and the noise of the road did not bother us at all....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (2)
"The house was fantastic. It had more rooms than we needed, everything was clean, the dining/living area had a lot of lighting, and there was a large fenced in backyard which our dogs loved running around in. It was a great getaway for us as we were coming from Brooklyn. Grocery stores were only 15 min away. Would highly recommend booking! When there was a minor issue, our host Lindsey was very communicative and had it solved right away!"
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!
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 types of properties in Western Massachusetts you may be interested in

MGM Springfield

4.0 star property
8.8 out of 10, Excellent, (1290)
"Quick night away for a comedy show and it was better than I expected. What a wonderful location. "
The price is €183
includes taxes & fees
18 Feb - 19 Feb
MGM Springfield

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2368)
"Had stayed before. We really like the property "
The price is €147
includes taxes & fees
18 Feb - 19 Feb
D. Hotel Suites & Spa

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1762)
"In door pool was very nice. Room was clean and had all the basics. "
The price is €130
includes taxes & fees
23 Feb - 24 Feb
Vacation Village in the Berkshires
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.