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Western Massachusetts Vacation Rentals

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Vacation Rentals in Western Massachusetts

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Hancock, MA
Situated in Hancock, this condo building is 0.1 mi (0.1 km) from Jiminy Peak Mountain Resort and within 6 mi (10 km) of Mount Greylock State Reservation and ...
4.2/5Excellent! (1,393 reviews)
"Our two bedroom suite was very clean, Mountain View, very spacious. The property itself offers great amenities for families like mine. My kids enjoyed every min. I will definitely go back"

Reviewed on Jul 24, 2021

Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
The price is $159 per night from Aug 2 to Aug 2
Located in the mountains, this Hancock condo resort offering ski-in/ski-out access is 6.1 mi (9.7 km) from Mount Greylock State Reservation Visitor Center and ...
4/5Very Good! (716 reviews)
"very relaxing ,beautiful view , friendly staff"

Reviewed on Jul 29, 2021

Jiminy Peak Mountain Resort
The Ponds at Foxhollow by Capital Vacations

The Ponds at Foxhollow by Capital Vacations

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Situated in the entertainment district, this condo building is within 3 mi (5 km) of The Mount, Housatonic River, and Animagic Museum of Animation. Lee Library ...
4.2/5Very Good! (49 reviews)
"Beautiful maintained property"

Reviewed on Jul 17, 2021

The Ponds at Foxhollow by Capital Vacations
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Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket, MA
Located in Sherwood Forest, this romantic cabin is within 6 mi (10 km) of Iroquis Waterfront, Jacob's Pillow, and October Mountain State Forest. Becket Land ...
4.5/5Wonderful! (81 reviews)
Cabin in the woods
"A couple of small issues but we’re resolved quickly. Property was well Thought out and supplied."

Reviewed on Jul 9, 2021

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Picon Cozy

Picon Cozy

Springfield, MA
The price is $75 per night from Aug 2 to Aug 2
Located in Sixteen Acres, this vacation home is 1.8 mi (2.9 km) from Fresenius Medical Care at Kindred Hospital Park View and 2.8 mi (4.6 km) from Springfield ...
4.4/5Excellent! (5 reviews)
Good stay
"Good stay"

Reviewed on Jul 14, 2021

Picon Cozy
Etinde House is Located ten Minutes From Umass, Amherst College, Hampshire Mall, Mount Holyoke College and a Minute From Hampshire College

Etinde House is Located ten Minutes From Umass, Amherst College, Hampshire Mall, Mount Holyoke College and a Minute From Hampshire College

Amherst, MA
The price is $700 per night from Aug 2 to Aug 2
Situated in Amherst, this vacation home is 0.9 mi (1.4 km) from Hampshire College and 3.1 mi (4.9 km) from Amherst College. Eric Carle Museum of Picture Book ...
2/5 (2 reviews)
Perfect location and size but could have been cleaner
"I have contacted the owner about our cleanliness issues and he was very receptive. Much of it was because of a mouse and droppings everywhere. We weren't notified that we needed blankets. Also there is no information available on things like recycling and what to do on departure. Again, the owner ..."

Reviewed on Jul 22, 2021

Etinde House is Located ten Minutes From Umass, Amherst College, Hampshire Mall, Mount Holyoke College and a Minute From Hampshire College
Kimball Upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Kimball Upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Amherst, MA
The price is $100 per night from Aug 29 to Aug 29
This family-friendly Amherst vacation home is located in a rural location, within 3 mi (5 km) of Puffers Pond South Beach and University of Massachusetts-Amherst. ...
4.8/5Exceptional! (42 reviews)
comfortable place in a great location
"A spacious and comfortable apartment within easy driving distance of Amherst, with a great cafe just two blocks away, and a nearby walking path to a delightful pond and natural area."

Reviewed on May 18, 2021

Kimball Upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
!!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

Springfield, MA
The price is $250 per night from Aug 4 to Aug 4
This family-friendly Springfield vacation home is located in the mountains, within 1 mi (2 km) of Zoo in Forest Park and Education Center and Forest Park. Naismith ...
4.8/5Exceptional! (14 reviews)
Awesome stay in Springfield, MA
"We had a wonderful time at Rose's place in Springfield, MA over July 4 weekend. The neighborhood is very quiet. The driveway parking is great as on street parking is quite limited. The beds were comfy! The house was so clean and sparkled! There are a lot of great extras - toiletries and coffee and ..."

Reviewed on Jul 20, 2021

!!upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself
NEW Secluded A-frame Cabin: Fire Pit, Walk to Lake

NEW Secluded A-frame Cabin: Fire Pit, Walk to Lake

Becket, MA
Located in Sherwood Forest, this cabin is 2.8 mi (4.5 km) from Iroquis Waterfront and within 6 mi (10 km) of October Mountain State Forest and Jacob's Pillow. ...
4.7/5Exceptional! (3 reviews)
An Amazing Getaway
"We really enjoyed our stay at the A-Frame cabin. The place is just as great as it looks in the pictures. Such a cozy & comfortable place to stay! Communication with Kathy & Chris was top notch. They were excellent hosts. The cabin felt so secluded with the lake right across from it. We can't wait ..."

Reviewed on Mar 31, 2021

NEW Secluded A-frame Cabin: Fire Pit, Walk to Lake
Comfort, Luxury, Privacy

Comfort, Luxury, Privacy

Amherst, MA
The price is $105 per night from Aug 4 to Aug 4
Situated in a rural location, this apartment building is 0.5 mi (0.8 km) from Puffers Pond South Beach and 2.9 mi (4.7 km) from University of Massachusetts-Amherst. ...
4.8/5Exceptional! (18 reviews)
Awesome as always.
"Have stayed here multiple times, and can't say enough. Communication and check-in process is smooth. Quiet, close to campus and very reasonable price. Will be back soon."

Reviewed on Jun 10, 2021

Comfort, Luxury, Privacy
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Williamsburg, MA
Situated in Williamsburg, this cabin is within 9 mi (15 km) of Westfield River, Swift River, and Chesterfield Gorge. Chapel Brook and David Mustante Beach are ...
4.3/5Excellent! (16 reviews)
Very clean
"If you are looking for peace and quiet this is the place for you, perfect secluded area in the woods. Definitely relaxing.!"

Reviewed on Jul 22, 2021

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Cozy Home

Cozy Home

3.5 out of 5
7 Worthy St, Springfield, MA
The price is $170 per night from Aug 3 to Aug 3
Situated in Springfield, this vacation home is 1 mi (1.7 km) from Mercy Hospital and within 3 mi (5 km) of Springfield Armory and MassMutual Center. MGM Springfield ...
Cozy Home
Cozy Agawam Studio w/ Yard: 2 Miles to Six Flags!

Cozy Agawam Studio w/ Yard: 2 Miles to Six Flags!

Agawam, MA
Situated in Agawam, this apartment building is 1.2 mi (1.9 km) from Six Flags New England and 3 mi (4.8 km) from Eastern States Exposition. Westfield River is ...
5/5Exceptional! (5 reviews)
Great stay!
"Our hosts were so sweet and thoughtful! The apartment is adorable! We were greeted with a plate of delicious cookies and a bottle of champagne!"

Reviewed on Oct 16, 2019

Cozy Agawam Studio w/ Yard: 2 Miles to Six Flags!
Cabin w/3 Acres, Tennis+bball Courts by 4 Ski Mtns

Cabin w/3 Acres, Tennis+bball Courts by 4 Ski Mtns

Sandisfield, MA
Situated in Sandisfield, this cabin is within 9 mi (15 km) of Otis Ridge, Ashintully Gardens, and Beartown State Forest. Bidwell House Museum and County Beach ...
4.7/5Exceptional! (12 reviews)
Lovely place
"We were mostly stuck inside the whole time because of rainy cold weather, but the house was perfect for a gathering of three families. It was clean and solid and all around a great time. Krystal was a perfect property manager!"

Reviewed on Jun 15, 2021

Cabin w/3 Acres, Tennis+bball Courts by 4 Ski Mtns
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

Williamstown, MA
Situated in Williamstown, this vacation home is 2.1 mi (3.4 km) from Jiminy Peak Mountain Resort and within 6 mi (10 km) of Pittsfield State Forest and Mount ...
5/5Exceptional! (6 reviews)
A lovely relaxing stay
"We had such a nice time. It was great being able to just relax in front of the fire place for a couple days. Very peaceful."

Reviewed on May 7, 2021

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!
Beautiful 2 Bedroom Apartment in the Lenox Dale Ma

Beautiful 2 Bedroom Apartment in the Lenox Dale Ma

Lee, MA
Situated in Lee, this apartment building is within 1 mi (2 km) of Housatonic River and Wood's Pond. Berkshire Scenic Railway Museum and The Mount are also within ...
4.9/5Exceptional! (7 reviews)
Cozy Berkshire Getaway
"This apartment was spacious and just right for our family of 4. The location was central to the ski mountains, which was important to us. The little market right across the street was handy, too. The owners were super responsive and helpful when we had questions. Washer/dryer was convenient so we ..."

Reviewed on Mar 7, 2021

Beautiful 2 Bedroom Apartment in the Lenox Dale Ma
Serene Shelburne Studio Cabin W/spring-fed Pool!

Serene Shelburne Studio Cabin W/spring-fed Pool!

Shelburne Falls, MA
Situated in Shelburne Falls, this cabin is within 6 mi (10 km) of Old Greenfield Village, High Ledges Wildlife Sanctuary, and Greenfield Community College. Bardwell's ...
4.4/5Excellent! (8 reviews)
Great little cabin!
"Perfect little cabin in the woods. You feel a million miles away from the hustle and bustle of a busy town yet you’re right around to corner to a lot of conveniences. Love it."

Reviewed on Nov 10, 2019

Serene Shelburne Studio Cabin W/spring-fed Pool!
Honeysuckle Rose Cottage

Honeysuckle Rose Cottage

Pittsfield, MA
Situated in Pittsfield, this vacation home is within 2 mi (3 km) of Colonial Theater, Berkshire Museum, and Berkshire Athenaeum. Housatonic River and Canoe Meadows ...
4.5/5Wonderful! (2 reviews)
Quaint and Beautiful Little Cottage
"We loved staying here! It was quaint and relaxing, just what we wanted. Despite the age of the cottage the heaters throughout kept us nice and warm. We were cozy the whole time. Some great books to read on the shelves and the TV was set up with streaming services and cable. Not a far drive from trails ..."

Reviewed on Mar 11, 2021

Honeysuckle Rose Cottage
Spacious 3BR 3 BA on Jiminy Mountain Resort 1900 Sqft w Tons of Perks

Spacious 3BR 3 BA on Jiminy Mountain Resort 1900 Sqft w Tons of Perks

Hancock, MA
Located in the mountains, this Hancock property offering ski-in/ski-out access is 0.2 mi (0.3 km) from Jiminy Peak Mountain Resort and within 9 mi (15 km) of ...
5/5Exceptional! (5 reviews)
"The house was equipped with every little detail"

Reviewed on Jul 30, 2021

Spacious 3BR 3 BA on Jiminy Mountain Resort 1900 Sqft w Tons of Perks
Jiminy Peak 4 Level Deluxe SKI Condo- 3+ Bedrooms, 2 Baths, Whirlpool,sauna More

Jiminy Peak 4 Level Deluxe SKI Condo- 3+ Bedrooms, 2 Baths, Whirlpool,sauna More

Lanesborough, MA
This family-friendly Lanesborough condo building is located in the mountains, within 3 mi (5 km) of Jiminy Peak Mountain Resort, Mount Greylock State Reservation ...
4.6/5Exceptional! (13 reviews)
Great ski vacation
"Lovely, well-kept property with a very homey feel. Marc was very responsive when I reached out to him with a question. We had a wonderful time playing games in front of the fire and snow shoeing in the area. The kids had a great time skiing"

Reviewed on Feb 26, 2021

Jiminy Peak 4 Level Deluxe SKI Condo- 3+ Bedrooms, 2 Baths, Whirlpool,sauna More
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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.

Large Group Cabins Western Massachusetts

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket, MA
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cabin w/3 Acres, Tennis+bball Courts by 4 Ski Mtns

Cabin w/3 Acres, Tennis+bball Courts by 4 Ski Mtns

Sandisfield, MA
Cabin w/3 Acres, Tennis+bball Courts by 4 Ski Mtns
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 months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Western Massachusetts vacation rentals range between $75 per night and $700 per night.

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.