Holiday Rentals in Western Massachusetts

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Holiday Rentals in Western Massachusetts

Our top choices for Western Massachusetts holiday rentals

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1975)
"Beautiful location!"
The price is €111
includes taxes & fees
7 Sept - 8 Sept
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (969)
"Quiet, clean, accessible. "
The price is €153
includes taxes & fees
2 Sept - 3 Sept
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is €94
includes taxes & fees
2 Sept - 3 Sept
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (126)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

HOMEY HOMEY

3.4 out of 10, (3)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
The price is €147
includes taxes & fees
29 Aug - 30 Aug
HOMEY HOMEY

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....

PICON COZY

7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is €146
includes taxes & fees
7 Sept - 8 Sept
PICON COZY

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is €924
includes taxes & fees
2 Sept - 3 Sept
Hancock Village Inn at Jiminy Peak

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Bear Creek Cabin

10.0 out of 10, Exceptional, (37)
"Enjoyed our stay"
The price is €526
includes taxes & fees
31 Aug - 1 Sept
Bear Creek Cabin

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course

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

9.0 out of 10, Wonderful, (26)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

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

9.6 out of 10, Exceptional, (34)
"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 €297
includes taxes & fees
31 Aug - 1 Sept
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

9.0 out of 10, Wonderful, (23)
"Check in was easy. This met all of our needs. "
The price is €685
includes taxes & fees
31 Aug - 1 Sept
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (10)
"The penthouse was beautiful and spacious. The Host Lea was very congenial and offered great suggestions for the location. I will definitely be coming back "
The price is €236
includes taxes & fees
7 Sept - 8 Sept
Park Street Penthouse Apartment

5 bedroom in the center of Springfield .

9.0 out of 10, Wonderful, (8)
"As advertised, great communication, would stay there again!"
5 bedroom in the center of Springfield .

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (125)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Place was super clean. Beds were comfortable. Location was great."
The price is €345
includes taxes & fees
3 Sept - 4 Sept
Florida Mountain Log Cabin!
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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Top Western Massachusetts Hotel Reviews

Find out more about Western Massachusetts

Find out more about Western Massachusetts

Everything you need to know about Western Massachusetts holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Western Massachusetts holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Western Massachusetts holiday 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 and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Western Massachusetts holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Western Massachusetts holiday rentals we have selected for you start as low as €94 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Western Massachusetts rentals

At Expedia, we put the best Western Massachusetts holiday 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 holiday.

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.