Compare Western Massachusetts Vacation Rentals

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Western Massachusetts Rentals

Free Cancellation

Reserve now, pay when you stay

25.8 mi from city center

$119 nightly

$133 total

Mar 8 - Mar 9

Total with taxes and fees

Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.

Pool

Parking included

27.65 mi from city center

$168 nightly

$188 total

Mar 8 - Mar 9

Total with taxes and fees

Guests staying at Huttopia Berkshires enjoy an outdoor pool, free WiFi in public areas, and a picnic area. You can put free parking to good use if you drive. Staff members can help with accommodation requests, and provide front-desk service during limited hours.

Pool

Pet friendly

22.15 mi from city center

The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. Helpful staff is there to provide a safe deposit box at the front desk, as well as offer insight about the area. Additional amenities include a sauna, free WiFi in public areas, and an outdoor tennis court.

Pool

Kitchen

Free Cancellation

Reserve now, pay when you stay

25.68 mi from city center

$145 nightly

$163 total

Apr 7 - Apr 8

Total with taxes and fees

At Jiminy Peak Mountain Resort, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with tours or tickets, luggage storage, and securing valuables. Other amenities at this ski condominium resort include 2 hot tubs, outdoor tennis courts, and free WiFi in public areas.

Pool

Hot Tub

27.07 mi from city center

$282 nightly

$314 total

Mar 8 - Mar 9

Total with taxes and fees

At this vacation home, guests have access to an arcade/game room, laundry facilities, and a garden.

Kitchen

Washer

The Kemble- Built by a US Secretary of State in Lenox

21.85 mi from city center

Guests of this villa enjoy features like a gym, a sauna, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

26.62 mi from city center

Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

26.35 mi from city center

$1,000 nightly

$1,083 total

Mar 11 - Mar 12

Total with taxes and fees

This vacation home features a hot tub, an arcade/game room, and a library. Other amenities at this family-friendly vacation home include laundry facilities and barbecue grills.

Hot Tub

Kitchen

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

28.52 mi from city center

At this apartment, guests have access to features like laundry facilities. This smoke-free apartment building also has barbecue grills.

Kitchen

Washer

28.42 mi from city center

$246 nightly

$274 total

Mar 15 - Mar 16

Total with taxes and fees

At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.

Kitchen

Washer

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

22.39 mi from city center

At this cabin, guests have access to a gym, laundry facilities, and barbecue grills. Friendly staff can provide concierge services, and also offer advice about sightseeing.

Kitchen

Washer

Secluded Family Getaway w/ On-Site Creek in Hawley

16.05 mi from city center

Guests staying at this vacation home have access to a garden and barbecue grills.

Kitchen

Washer

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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.

Western Massachusetts Large Group Rentals

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington MA

10/10 Exceptional! (56 reviews)

Lovely 2nd Floor Apartment

Greenfield MA

$180 nightly

$201 total

Mar 10 - Mar 11

Total with taxes and fees

10/10 Exceptional! (49 reviews)

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA

10/10 Exceptional! (12 reviews)

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont MA

9.8/10 Exceptional! (29 reviews)

Home in Great Barrington

Great Barrington MA

$246 nightly

$274 total

Mar 15 - Mar 16

Total with taxes and fees

9.8/10 Exceptional! (27 reviews)

Family Ski Getaway in the Berkshires

Great Barrington MA

$282 nightly

$314 total

Mar 8 - Mar 9

Total with taxes and fees

9/10 Wonderful! (12 reviews)

How to Book Vacation Rentals in Western Massachusetts

🏠 What is the best price for Western Massachusetts vacation rentals?

Western Massachusetts vacation rentals range in price, starting at $133 per night.

🏠 What types of vacation rentals in Western Massachusetts can I rent?

Orbitz offers a wide range of Western Massachusetts rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Western Massachusetts condo rentals.

🏠 Is it free to cancel my Western Massachusetts vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.

🏠 How do I find the best deals to rent a Western Massachusetts vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Western Massachusetts. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.

🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.

🏠 What are the advantages of booking a vacation rental in Western Massachusetts?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Western Massachusetts apartments and enjoy an extended stay.

🏠 Why should I book my vacation rental with Orbitz in Western Massachusetts?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Western Massachusetts package deals will get you even more savings.