Compare The Berkshires Vacation Rentals
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The Berkshires Rentals

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

The Ponds at Foxhollow

Huttopia Berkshires

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

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

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Comfortable Berkshires retreat on mtn resort, SISO

Hancock Village Inn at Jiminy Peak
The Berkshires Large Group Rentals

Contemporary Berkshire Home with Views of Taconic Golf Course

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

19th c. Barn in the Berkshires

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Spacious 5-bedroom house in charming Lee with WiFi
How to Book Vacation Rentals in The Berkshires
🏠 What is the best price for The Berkshires vacation rentals?
The Berkshires vacation rentals range in price, starting at $115 per night.
🏠 What types of vacation rentals in The Berkshires can I rent?
Orbitz offers a wide range of The Berkshires 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 The Berkshires condo rentals.
🏠 Is it free to cancel my The Berkshires 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 The Berkshires 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 The Berkshires. 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 The Berkshires?
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 The Berkshires apartments and enjoy an extended stay.
🏠 Why should I book my vacation rental with Orbitz in The Berkshires?
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 The Berkshires package deals will get you even more savings.
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