Search Condo 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

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1931)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is HK$721
HK$891 total
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

9.4 out of 10, Exceptional, (25)
"We had a great experience with this rental. Nice location for skiing on and off the mountain and close to the heart of the ski facility. "
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Property grounds

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

10.0 out of 10, Exceptional, (39)
"3rd time staying here. The host is great, the place is clean, and the location couldn't be better!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.
Interior

Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.

7.0 out of 10, Good, (8)
"The house was very clean. It was difficult finding the rental and required calling the host. There’s a bbq grill but no grill equipment like tongs, spatula or scraper, the outside fire table did not work and the back yard had trash on the ground. The kitchen hot mitts were crusty and dirty, fixtures were falling off in the bathroom and the place needs another mirror for getting ready"
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.
UNIQUE - 1BR Country Condo @ Jiminy Peak
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Clean and quiet, nicely decorated! "
The price is HK$629
HK$2,272 total
includes taxes & fees
6 Aug - 7 Aug
UNIQUE - 1BR Country Condo @ Jiminy Peak
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Exterior

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

7.8 out of 10, Good, (6)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
The price is HK$1,287
HK$2,876 total
includes taxes & fees
19 Aug - 20 Aug
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Duplex w/ Fire Pit ~ 1 Mi to MGM Springfield!
Dining

Duplex w/ Fire Pit ~ 1 Mi to MGM Springfield!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Everything was great. We enjoyed our stay!"
Duplex w/ Fire Pit ~ 1 Mi to MGM Springfield!
Peaceful 1BR Condo with Pond View
Property grounds

Peaceful 1BR Condo with Pond View

8.0 out of 10, Very good, (1)
"The location was very close to Tanglewood and The Mount, but the front drive off the main road was really dark, no street lights, so we missed our turn a few times but did eventually find the place. The community was pretty and tranquil, we did not hear any noise at all. The WiFi was a little wonky but no big deal because we were able to get cell service. "
Peaceful 1BR Condo with Pond View
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Living area

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

10.0 out of 10, Exceptional, (3)
"Good base for Berkshires, responsive host, good rates, secure."
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub
Spa

1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub

10.0 out of 10, Exceptional, (1)
"You'll love this house, it feels just like home but more relaxing and enjoyable! We used the community heated pool and hot tub several times during our stay. The house is just as pictures, but better. Everything you could need is supplied n the rental, all you need is food and clothes. We slept great at this house, better than any other vacation, no one got up early. The kitchen and grill were great to cook with. Staying at this house was very enjoyable!"
1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Fridge, microwave, oven, stovetop

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

10.0 out of 10, Exceptional, (32)
"Everything was spot on. Will be back!!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Exterior

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

10.0 out of 10, Exceptional, (6)
"It was exactly as described, perfect for a family stay with easy ski on and off. I was pleasantly surprised with all the amenities of the property. Would stay again!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Fridge, microwave, oven, stovetop

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

10.0 out of 10, Exceptional, (12)
"We'll be back!"
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

10.0 out of 10, Exceptional, (1)
"Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. "
Club Wyndham Bentley Brook Resort - 2 Bedroom
Berkshires Getaway < 1 Mi Skiing & Hiking!
Fridge, microwave, stovetop, dishwasher

Berkshires Getaway < 1 Mi Skiing & Hiking!

10.0 out of 10, Exceptional, (14)
"Location was perfect! Home is cozy and well equipped! Perfect getaway for our family with great hospitality."
Berkshires Getaway < 1 Mi Skiing & Hiking!
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Fridge, microwave, oven, stovetop

Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!

10.0 out of 10, Exceptional, (1)
"I really enjoyed my stay at this Vrbo. Everything was well stocked (bedroom/bathroom/kitchen linens, cleaning supplies, kitchen appliances / serveware etc). The futon pulled out was comfortable. The flat is in a great location that is walking-distance to cafes/restaurants. Tre was an excellent host!"
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Welcome to Honey Spot!
Property grounds

Welcome to Honey Spot!

9.8 out of 10, Exceptional, (27)
"House was extremely clean. Fully stocked. Host was very helpful. Would stay again."
Welcome to Honey Spot!
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
Kim 3-night trip
Posted 1 day ago
Vacation Village in the Berkshires

Frequently asked questions

How much do condos in Western Massachusetts cost?
Condos in Western Massachusetts range from HK$629 to HK$1,287 per night. These properties offer loads of space for your whole crew at a price that won't stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Western Massachusetts?
Western Massachusetts has 68 condos to pick from. Enter your destination and travel dates and book your perfect stay today.
Why book your condo in Western Massachusetts with Expedia?
Booking a condo in Western Massachusetts is as easy as working out your travel dates and choosing a place that meets your needs. In search of something luxurious or low cost, or a stay that also comes with a kitchen? Use Expedia's search filters to narrow your results even further and find your ideal match.