Western Massachusetts Holiday Rentals

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Holiday Rentals in Western Massachusetts

Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (858)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is NZ$278
includes taxes & fees
2 Jun - 3 Jun
Jiminy Peak Mountain Resort
7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
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Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Fridge, microwave, oven, stovetop
PICON COZY
8.0 out of 10, Very good, (43)
"Fidelis demonstrated exceptional professionalism throughout our interaction. He was remarkably accommodating, consistently honest, and promptly addressed any inquiries I had, usually within minutes. On the rare occasion that he couldn't respond immediately, he took the time to provide an explanation and offer his apologies. Recently, my son relocated to this area for work, and thanks to Fidelis, I can now rest assured that my 24-year-old son, who has yet to experience living on his own, is safe...
The price is NZ$277
includes taxes & fees
31 May - 1 Jun
PICON COZY
Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Terrace/patio
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, (81)
"Comfortable and convenient"
The price is NZ$340
includes taxes & fees
29 May - 30 May
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Property grounds
The Ponds at Foxhollow by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, (110)
"Comfortable condo accommodations. Ample size, Workable kitchen. Comfortable bed. Lovely setting. And a community facility with a pool, workout equipment, and sauna too! Small but tangible complaint: outside lighting is very bright and shines into BR window. "
The Ponds at Foxhollow by Capital Vacations
Property grounds
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (52)
"Wonderful place to stay, had a great time lots of instruments to try, had lots of space to spread out and hangout, the hot tub was very nice and clean. Overall had a fantastic stay the lighted walkway is amazing! All the amenities available where also great, Jon was a great host and we had a great time speaking with him!"
The price is NZ$389
includes taxes & fees
4 Jun - 5 Jun
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is NZ$438
includes taxes & fees
29 May - 30 May
Perfect Vacation Get Away - Historical New Marlborough
Fridge, microwave, oven, stovetop
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
9.0 out of 10, Wonderful, (18)
"The property is as advertised. If you have a lot of people that just needs a place to sleep and collect yourseves, this is a wonderful place fir the price. The owner is a pleasure to work with and very responsive. Also met some of the neighbors and it is reassuring that they all watch out for one another."
The price is NZ$944
includes taxes & fees
29 May - 30 May
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Dining
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
9.6 out of 10, Exceptional, (28)
"It was nice stay!"
The price is NZ$511
includes taxes & fees
2 Jun - 3 Jun
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Microwave, oven, stovetop, dishwasher
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
4.0 out of 10, (1)
"Location has the potential to be great but it is run down and needs A LOT of work. From first walking in, refrigerator was so dirty/dusty you could run your finger down it and have a film on your hand. Wood flooring in kitchen area is warped because of an obvious leak in the ceiling. Ceiling in the kitchen has brown water stains in the ceiling, floor tiles in the upstairs bathroom are cracked, ants kept coming in from outside, food left in the fridge and trash was left in and on the garbage can,...
The price is NZ$365
includes taxes & fees
29 May - 30 May
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (11)
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Exterior
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
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See all available properties in Western Massachusetts
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.

Other types of properties in Western Massachusetts you may be interested in

8 restaurants, breakfast, lunch, dinner served; American cuisine
MGM Springfield
4.0 star property
8.8 out of 10, Excellent, (1008)
"Everyone was kind and helpful"
The price is NZ$275
includes taxes & fees
2 Jun - 3 Jun
MGM Springfield
Lobby
Quality Inn West Springfield
2.5 star property
7.2 out of 10, Good, (1004)
"The hotel was clean, quiet and safe. The breakfast was good and accessible. "
The price is NZ$164
includes taxes & fees
3 Jun - 4 Jun
Quality Inn West Springfield
Indoor pool
D. Hotel Suites & Spa
3.0 star property
9.4 out of 10, Exceptional, (2278)
"This is a charming hotel that we’ve stayed in a couple of times. Staff is always excellent and our stay very comfortable."
The price is NZ$282
includes taxes & fees
29 May - 30 May
D. Hotel Suites & Spa
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Western Massachusetts holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Western Massachusetts. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Western Massachusetts. Seeing all the best attractions is bound to make you fall in love with Western Massachusetts. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Western Massachusetts short-term rentals, that won’t be hard to do.

Recent reviews of Western Massachusetts properties
Expedia verified reviews

Hilton Garden Inn-Springfield, MA

Hilton Garden Inn-Springfield, MA

5/5 Excellent
"Great for the money"
A verified traveller stayed at Hilton Garden Inn-Springfield, MA
Posted 8 hours ago
Hilton Garden Inn-Springfield, MA