A lake with a rocky shoreline and a forested island.

Western Massachusetts Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Western Massachusetts vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,090 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is ₩131,093
₩177,390 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,561 reviews)
"Place was clean and well equipped, pool and amenities were great too !"
United States
Nyra
The price is ₩120,384
₩149,672 total
includes taxes & fees
Aug 31 - Sep 1
Vacation Village in the Berkshires
A wooden cabin with a covered deck, a fire pit, and string lights.

3. Huttopia Berkshires

Huttopia Berkshires
2.5 star property
Williamstown
9.4 out of 10, Exceptional, (16 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ₩134,294
₩150,006 total
includes taxes & fees
Sep 8 - Sep 9
Huttopia Berkshires
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

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

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is ₩131,254
₩335,402 total
includes taxes & fees
Aug 30 - Aug 31
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
A modern kitchen with white cabinets, a wooden staircase, and a dining area with a table and chairs.

5. Chef's Kitchen Family Basecamp Amherst

Chef's Kitchen Family Basecamp Amherst
3.0 star property
East Village Historic District
The price is ₩502,954
₩936,814 total
includes taxes & fees
Sep 1 - Sep 2
Chef's Kitchen Family Basecamp Amherst
A modern dining area with a glass table, leather chairs, and a contemporary light fixture.

6. Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is ₩645,907
₩940,024 total
includes taxes & fees
Aug 26 - Aug 27
Newly Renovated 2 floor Getaway
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

7. Steps to Holyoke Medical Center! Remote-work Hub

Steps to Holyoke Medical Center! Remote-work Hub
3.0 star property
Holyoke
The price is ₩214,804
₩666,003 total
includes taxes & fees
Aug 30 - Aug 31
Steps to Holyoke Medical Center! Remote-work Hub
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

8. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (169 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
The price is ₩178,754
₩200,224 total
includes taxes & fees
Aug 27 - Aug 28
Micosta Leisure Inn
A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

9. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is ₩525,016
₩902,875 total
includes taxes & fees
Sep 2 - Sep 3
3 Mi to Mount Snow: Spacious West Dover Home
A red house with a porch, surrounded by a grassy yard and trees.

10. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is ₩170,249
₩545,887 total
includes taxes & fees
Aug 26 - Aug 27
Two Brooks Lodge

11. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
The price is ₩379,946
₩547,468 total
includes taxes & fees
Aug 26 - Aug 27
Trumbull Apartments
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

12. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ₩309,483
₩765,639 total
includes taxes & fees
Sep 6 - Sep 7
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Western Massachusetts Hotel Reviews

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

10/10 Excellent
"I loved my room, very spacious, clean and everything needed including refrigerator, microwave and bathroom utilities. I would stay again if in the area. Breakfast was good and the ladies were very nice. Also front desk lady. Excellent stay."
Alberto 1-night trip
Posted 3 hours ago
Holiday Inn Express Springfield Downtown by IHG

Find out more about Western Massachusetts

Search for Vacation rentals in Western Massachusetts on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Western Massachusetts using one of the methods below:

  • View our selection of featured Vacation rentals in Western Massachusetts
  • Use the map to find apartments and other Vacation homes in the Western Massachusetts neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Western Massachusetts while they last

Look no further and take a look at our great range of rental properties in Western Massachusetts!