Photo by Tu Nguyen
Search and Rent Western Massachusetts Condos
- Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
- OneKeyCashEarn OneKeyCash on all your eligible bookings
- Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Western Massachusetts condo rentals

Condo in Williamstown
Vacation Village in the Berkshires8.8 out of 10, Excellent, (2182)
$126 nightly
The price is $141
Jan 4 - Jan 5, 2026
Total with taxes and fees
$260 nightly
The price is $295
Dec 31 - Jan 1, 2026
Total with taxes and fees

Condo in Hancock
UNIQUE - 1BR Country Condo @ Jiminy Peak10.0 out of 10, Exceptional, (14)
$317 nightly
The price is $354
Dec 24 - Dec 25
Total with taxes and fees

Condo in Hancock
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 78.0 out of 10, Very Good, (8)
$301 nightly
The price is $336
Jan 5 - Jan 6, 2026
Total with taxes and fees

Condo in Hancock
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous9.0 out of 10, Wonderful, (2)
$270 nightly
The price is $302
Jan 6 - Jan 7, 2026
Total with taxes and fees

Condo in Enfield
Spacious 4-bedroom condo with AC and WiFi in charming Enfield10.0 out of 10, Exceptional, (2)
$372 nightly
The price is $421
Dec 31 - Jan 1, 2026
Total with taxes and fees

8.8 out of 10, Excellent, (32)
$406 nightly
The price is $459
Jan 21 - Jan 22, 2026
Total with taxes and fees

Condo in West Dover
Cozy 3 bedroom condo 2.5 miles to Mount Snow9.0 out of 10, Wonderful, (45)
$272 nightly
The price is $307
Jan 14 - Jan 15, 2026
Total with taxes and fees
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.
Find vacation rentals that suit your style
Cabins
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Western Massachusetts Hotel Reviews

The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Find out more about Western Massachusetts
Western Massachusetts Condo Rentals information
Number of reviews | 2,289 |
|---|---|
Accommodation | 48 Condo Rentals |
Lowest Price | $141 |
Highest Price | $1,130 |
Frequently asked questions
Explore a world of travel with Expedia
- Cottages in Chesterfield
- Farmstay in Chesterfield
- Cabin Rentals in Chesterfield
- Chesterfield Hotels
- 5 Star Hotels in Chesterfield
- 3 Star Hotels in Chesterfield
- 4 Star Hotels in Chesterfield
- Hotels near Chesterfield Gorge
- Norwich Lake Hotels
- Hotels near Petticoat Hill
- B&B in Williamsburg
- Cabin Rentals in Williamsburg
- Vacation Homes in Williamsburg
- Motels in Williamsburg
- Cabin Rentals in Goshen
- Motels in Goshen
- B&B in Goshen
- Vacation Homes in Goshen
- Williamsburg Hotels
- 5 Star Hotels in Williamsburg
- Westhampton Hotels
- Goshen Hotels
- Resorts in Worthington
- B&B in Worthington
- Cabin Rentals in Worthington
- Guest Houses in Worthington
- Worthington Hotels
- 5 Star Hotels in Worthington
- 4 Star Hotels in Worthington
- Hotels near Swift River
- Vacation Homes in Haydenville
- B&B in Haydenville
- Motels in Haydenville
- B&B in Cummington
- Cabin Rentals in Cummington
- Motels in Cummington
- Haydenville Hotels
- 5 Star Hotels in Haydenville
- Hotels near Look Memorial Park
- Cummington Hotels
- 4 Star Hotels in Cummington
- 5 Star Hotels in Cummington
- 3 Star Hotels in Cummington
- Hotels near Littleville Lake
- B&B in Florence
- Motels in Florence
- Florence Hotels
- 4 Star Hotels in Florence
- B&B in North Hatfield
- Hotels near Chapel Brook
- Northampton Hotels
- Hotels near Congregation Beth Israel
- B&B in Northampton
- Motels in Northampton
- Cabin Rentals in Northampton
- Condo Rentals in Huntington
- Cottages in Huntington
- Cottages in Northampton
- Guest Houses in Northampton
- Vacation Homes in Northampton
- RV Parks in Northampton
- West Hatfield Hotels
- B&B in Middlefield
- Resorts in Middlefield
- Condo Resorts in Middlefield
- Lodges in Chester
- Cabin Rentals in Chester
- Motels in Chester









































