Western Massachusetts Vacation Rentals

Save 10% or more on select stays with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Vacation Rentals in Western Massachusetts

Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA, 01237
The price is $149 per night from Sep 5 to Sep 6
Stay at this 3-star ski condo in Hancock. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. ...
4/5 Very Good! (797 reviews)
"Was a very good experience place was clean room very nice , small kitchen, small living room big bathroom and nice bedroom"

Reviewed on Aug 8, 2022

Jiminy Peak Mountain Resort
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Hancock, MA, 01237
Stay at this 3-star condo in Hancock. Enjoy free WiFi, free parking, and a children's pool. Our guests praise the pool and the clean rooms in our reviews. Popular ...
4.2/5 Excellent! (1,564 reviews)
"Excellent kitchen amenities and supplies. Spacious rooms including a large bathroom. Limited number of units per building. The decor is very drab. Dull colors even in the prints on the walls."

Reviewed on Jul 25, 2022

Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA, 01240
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the spacious rooms in our reviews. Popular ...
4.3/5 Excellent! (74 reviews)
"This was a great space for a family vacation. On-site amenities including indoor and outdoor pools, tennis court, shuffleboard and playground were great for kids. Location is wonderful, just about 2 miles to Tanglewood and downtown Lenox with shops and restaurants. Condo is dated and areas of the ..."

Reviewed on Aug 2, 2022

The Ponds at Foxhollow by Capital Vacations
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Gorgeous Zen Suite- Sleeps 4- Ski On Off Jiminy Mtn- Must See Luxury
Enjoy free WiFi, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock State Reservation Visitor Center are located ...
5/5 Exceptional! (2 reviews)
This place was awesome!
"The massage table and defuser we're great for relaxing. We were able to have a self contained relaxation experience inside while still having the fun of so many activities just outside, even I'm the summer! Such a cute and convient space."

Reviewed on Aug 5, 2022

Gorgeous Zen Suite- Sleeps 4- Ski On Off Jiminy Mtn- Must See Luxury
Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA
Stay at this condo in Lenox. Enjoy an outdoor pool, WiFi, and a spa tub. Popular attractions Norman Rockwell Museum and The Mount are located nearby. Discover ...
4.7/5 Exceptional! (3 reviews)
Beautiful setting and great condo
"Loved the condo It had everything we needed! The owner was wonderful to communicate with Beautiful setting"

Reviewed on Aug 22, 2021

Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA
The Lodge @ America's Switzerland - The Mountains Are Calling!
Stay at this vacation home in North Adams. Enjoy WiFi, 2 bathrooms, and 3 bedrooms. Popular attractions Mass MoCA and Natural Bridge State Park are located nearby. ...
5/5 Exceptional! (1 review)
Breathtaking Views
"Lea is an amazing host. The property was beautiful, well maintained, and clean. You can’t get views any better than this. The coffee shop next door is so convenient and food and coffee are delicious. I was not aware that this property has multiple smaller cabins, hammocks, and picnic tables, yet ..."

Reviewed on Jun 24, 2022

The Lodge @ America's Switzerland - The Mountains Are Calling!
Lovley Romantic/fun en Suite With Hottub and Claw Foot Tub!
The price is $275 per night from Aug 16 to Aug 17
Stay at this chalet in North Adams. Enjoy WiFi, 1 bedroom, and air conditioning. Popular attractions Mass MoCA and Mount Greylock are located nearby. Discover ...
5/5 Exceptional! (1 review)
Great spot!
"Great view from the deck! Outdoor spaces lovely. Enjoyed the interesting architecture of the room & bath rooms. Clean, comfortable experience."

Reviewed on Aug 7, 2022

Lovley Romantic/fun en Suite With Hottub and Claw Foot Tub!
Beautiful romantic Private en suite
The price is $275 per night from Aug 16 to Aug 17
Enjoy WiFi, onsite parking, and a garden. Popular attractions Mass MoCA and Mount Greylock are located nearby. Discover genuine guest reviews for Beautiful romantic ...
Beautiful romantic Private en suite
Disney Magic Suite On Jiminy Peak Mtn Resort - Must See Gorgeous - Sleeps 4
Enjoy free WiFi, an outdoor pool, and a spa tub. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock State Reservation Visitor Center are located ...
5/5 Exceptional! (2 reviews)
Beautiful and clean
"We stayed in this magical suite at Jiminy Peak for a weekend. The suite was clean and well put together! The Disney theme was a lot of fun for our two girls and we made Mickey waffles, watched Finding Nemo and played a few Disney themed games! Easy to all the amenities, this is a great option for ..."

Reviewed on Jul 22, 2022

Disney Magic Suite On Jiminy Peak Mtn Resort - Must See Gorgeous - Sleeps 4
PICON COZY
Springfield, MA
The price is $75 per night from Aug 16 to Aug 17
Stay at this vacation home in Springfield. Enjoy WiFi, onsite parking, and a TV. Popular attractions MGM Springfield and Naismith Memorial Basketball Hall of ...
4/5 Very Good! (26 reviews)
Short & sweet
"My friend and I just needed a little getaway, and this house was a perfect little place to stay. Quiet neighborhood and attentive host. Thanks again!"

Reviewed on Apr 2, 2022

PICON COZY
Don't see what you're looking for?
See all available properties in Western Massachusetts
View all properties
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

MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA, 01103
The price is $116 per night from Aug 23 to Aug 24
MGM Springfield
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA, 01104
Fully refundableReserve now, pay when you stay
The price is $114 per night from Aug 23 to Aug 24
La Quinta Inn & Suites by Wyndham Springfield MA
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