Western Massachusetts Vacation Rentals

Vacation 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 $154
$169 total
includes taxes & fees
May 30 - May 31
Jiminy Peak Mountain Resort
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
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 $75
$170 total
includes taxes & fees
May 30 - May 31
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 $145
$208 total
includes taxes & fees
May 28 - May 29
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 $160
$239 total
includes taxes & fees
May 28 - May 29
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 $150
$271 total
includes taxes & fees
May 28 - May 29
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 $300
$581 total
includes taxes & fees
May 28 - May 29
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 $182
$314 total
includes taxes & fees
Jun 2 - Jun 3
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 $75
$225 total
includes taxes & fees
May 28 - May 29
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.

Western Massachusetts Vacation Rental Travel Info

Vacation rentals
47
Popular accommodation
Western Massachusetts private vacation homes
International airports
Boston, MA (BOS-Logan Intl.), Hartford, CT (BDL-Bradley Intl.) and Albany, NY (ALB-Albany Intl.)

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 $129
$169 total
includes taxes & fees
May 28 - May 29
MGM Springfield
Lobby
Quality Inn West Springfield
2.5 star property
7.2 out of 10, Good, (1003)
"The hotel was clean, quiet and safe. The breakfast was good and accessible. "
The price is $92
$103 total
includes taxes & fees
Jun 18 - Jun 19
Quality Inn West Springfield
Indoor pool
D. Hotel Suites & Spa
3.0 star property
9.4 out of 10, Exceptional, (2277)
"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 $136
$157 total
includes taxes & fees
Jun 10 - Jun 11
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.

Everything you need to know about Western Massachusetts vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Western Massachusetts vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Western Massachusetts vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Western Massachusetts vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Western Massachusetts. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Western Massachusetts in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Western Massachusetts rentals

At Expedia, we put the best Western Massachusetts vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Western Massachusetts rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Western Massachusetts vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Western Massachusetts. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Western Massachusetts properties
Expedia verified reviews

Holiday Inn Express Springfield Downtown, an IHG Hotel

Holiday Inn Express Springfield Downtown, an IHG Hotel

5/5 Excellent
"Front desk young lady was great very helpful,rooms very good and clean and quiet,only issue elevators need attention"
A verified traveler stayed at Holiday Inn Express Springfield Downtown, an IHG Hotel
Posted 2 days ago
Holiday Inn Express Springfield Downtown, an IHG Hotel