Search Holiday Rentals in Western Massachusetts

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Aug - 14 Aug
Tomorrow
14 Aug - 15 Aug
This weekend
15 Aug - 17 Aug
Next weekend
22 Aug - 24 Aug

Top Holiday Rentals in Western Massachusetts

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1945)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is 2.844.674 ₫
3.465.596 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (962)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is 4.175.658 ₫
4.664.211 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is 2.573.676 ₫
2.874.797 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (124)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
Newly Renovated 2 floor Getaway
Full-sized fridge, microwave, oven, dishwasher

Newly Renovated 2 floor Getaway

3.5 star property
The price is 12.260.188 ₫
17.842.934 ₫ total
includes taxes & fees
14 Aug - 15 Aug
Newly Renovated 2 floor Getaway
Westfield Vacation Rental w/ Porch, Pets Welcome!
Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
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.
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
"Slept well"
Maria 1-night trip
Posted 1 day ago
Holiday Inn Express Springfield Downtown by IHG