Western Massachusetts Vacation Rentals

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Mar 27 - Mar 29

Vacation Rentals in Western Massachusetts

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Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2159)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
$101 nightly
The price is $113
Dec 3 - Dec 4
Total with taxes and fees
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (135)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
$125 nightly
The price is $140
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very Good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
$178 nightly
The price is $199
Dec 3 - Dec 4
Total with taxes and fees
Jiminy Peak Mountain Resort
Exterior
Tiny Home with AC and WiFi in lovely Ludlow

Vacation Home in Ludlow

8.4 out of 10, Very Good, (8)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
United States
Matthew H.
$134 nightly
The price is $150
Dec 3 - Dec 4
Total with taxes and fees
Tiny Home with AC and WiFi in lovely Ludlow
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Apartment in Hancock

10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
$211 nightly
The price is $236
Dec 3 - Dec 4
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Apartment in Greenfield

8.8 out of 10, Excellent, (3)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
$186 nightly
The price is $208
Dec 7 - Dec 8
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Interior
Lovely 2nd Floor Apartment

Vacation Home in Greenfield

10.0 out of 10, Exceptional, (45)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
$181 nightly
The price is $202
Dec 3 - Dec 4
Total with taxes and fees
Lovely 2nd Floor Apartment
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$338 nightly
The price is $377
Dec 3 - Dec 4
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Vacation Home in Boston Road

9.2 out of 10, Wonderful, (13)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
$283 nightly
The price is $321
Dec 4 - Dec 5
Total with taxes and fees
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water

Apartment in Williamstown

10.0 out of 10, Exceptional, (10)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
New Studio In Town, By the Water
TV
Florida Mountain Log Cabin

Vacation Home in Florida

2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$316 nightly
The price is $339
Dec 3 - Dec 4
Total with taxes and fees
Florida Mountain Log Cabin
Property grounds
Welcome to Honey Spot!

Condo in Pine Point

9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
$262 nightly
The price is $297
Dec 31 - Jan 1, 2026
Total with taxes and fees
Welcome to Honey Spot!
3 bedrooms, iron/ironing board, WiFi, bed sheets
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Vacation Home in Boston Road

9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
$283 nightly
The price is $321
Dec 3 - Dec 4
Total with taxes and fees
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in Hancock

10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
$211 nightly
The price is $236
Dec 3 - Dec 4
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Terrace/patio
Cozy Home in Holyoke with 3 bedrooms

Vacation Home in Holyoke

9.8 out of 10, Exceptional, (12)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
United States
Eric W.
$288 nightly
The price is $322
Dec 3 - Dec 4
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$338 nightly
The price is $378
Dec 3 - Dec 4
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
$189 nightly
The price is $208
Dec 3 - Dec 4
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Outdoor dining
Downtown | Waterfront | Walk to Shops

Apartment in Williamstown

10.0 out of 10, Exceptional, (7)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
Downtown | Waterfront | Walk to Shops
Property grounds
The Creation Station is a cozy place so make yourself at home.

Vacation Home in Easthampton Ma.

10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
$248 nightly
The price is $277
Dec 3 - Dec 4
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Outdoor dining
2-Bdr Apt In Town, By the Water

Apartment in Williamstown

9.6 out of 10, Exceptional, (11)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
2-Bdr Apt In Town, By the Water
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Western Massachusetts

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 $113 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.

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