Compare Western Massachusetts Vacation Rentals
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Western Massachusetts Rentals

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

The Ponds at Foxhollow

Huttopia Berkshires

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Contemporary Berkshire Home with Views of Taconic Golf Course

PICON COZY

HOMEY HOMEY

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

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

Hancock Village Inn at Jiminy Peak
Western Massachusetts Large Group Rentals

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Lovely 2nd Floor Apartment

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Bring Your Pet & Visit Springfield: Westfield Home

Spacious 5-bedroom house in charming Lee with WiFi

Charming Berkshires Retreat – Minutes to Williamstown
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 $134 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.
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