A lake with a rocky shoreline and a forested island.

Western Massachusetts Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Western Massachusetts vacation rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,148 reviews)
"Clean & comfortable stay"
United States
Robert
$108 nightly
The price is $120
Oct 21 - Oct 22
Total with taxes and fees
Berkshire Mountain Lodge
Lobby

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,665 reviews)
"Love this place for a weekend getaway."
United States
Jacob
$122 nightly
The price is $136
Sep 22 - Sep 23
Total with taxes and fees
Vacation Village in the Berkshires
Exterior

3. Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
$219 nightly
The price is $245
Sep 22 - Sep 23
Total with taxes and fees
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Apartment (0 Bedroom) | Interior

4. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
$213 nightly
The price is $238
Sep 22 - Sep 23
Total with taxes and fees
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Exterior

5. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
$294 nightly
The price is $328
Sep 22 - Sep 23
Total with taxes and fees
Work, Play & Stay! Apt Near Holyoke Medical Center
Desk, iron/ironing board, travel crib, WiFi

6. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (77 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
$239 nightly
The price is $267
Sep 29 - Sep 30
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Interior

7. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (66 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
$197 nightly
The price is $220
Oct 12 - Oct 13
Total with taxes and fees
Lovely 2nd Floor Apartment
Property grounds

8. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
$200 nightly
The price is $224
Sep 22 - Sep 23
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior detail

9. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (9 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
$240 nightly
The price is $268
Oct 5 - Oct 6
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Interior

10. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
$445 nightly
The price is $497
Sep 22 - Sep 23
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
Interior

11. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
$260 nightly
The price is $290
Sep 24 - Sep 25
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
Interior

12. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$335 nightly
The price is $374
Sep 28 - Sep 29
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Smart TV, books, stereo

13. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (37 reviews)
"The host was so responsive and made sure everything was perfect! It was the cutest and most comfy set up! With an adorable town beach 5 min down the road! Highly recommend!"
United States
Nora M.
$201 nightly
The price is $212
Sep 23 - Sep 24
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
Property grounds

14. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveler
$399 nightly
The price is $422
Sep 22 - Sep 23
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
Flat-screen TV, books

15. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (12 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
$270 nightly
The price is $306
Sep 22 - Sep 23
Total with taxes and fees
Cozy First Floor Apartment. Located in a quiet neighborhood.
Coffee/tea maker, fridge, microwave, oven

16. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (33 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
$310 nightly
The price is $346
Oct 8 - Oct 9
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Property grounds

17. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (151 reviews)
"Great location"
United States
Will G.
$312 nightly
The price is $330
Oct 6 - Oct 7
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Interior

18. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
$163 nightly
The price is $182
Sep 22 - Sep 23
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Interior

19. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
$244 nightly
The price is $272
Sep 28 - Sep 29
Total with taxes and fees
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Property grounds

20. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
$392 nightly
The price is $438
Sep 22 - Sep 23
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"This was my family's 3rd or 4th time staying at this hotel & we love it. We'll keep going back. Its located on Congress Street in downtown Springfield, perfectly located 12 minutes from The Big E State Fair (which is primarily why we go to Springfield) but its also extremely close to The Basketball Hall of Fame. LaQuinta is very clean & the rooms are a pretty good size. There's a great bar in the lobby & for the past 3 years Kim has been our bartender. Kim is the best & creates all of these special fall cocktails. If you're staying at this hotel, definitely go see Kim...I cant find anything bad to say about this hotel & best part is that its extremely affordable too"
Joseph 2-night trip
Posted 9 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA

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 $120 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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