Compare The Berkshires Vacation Rentals

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The Berkshires Rentals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
28.42 mi from city center
$112 nightly
The price is $125 total per night
$125 total
Oct 30 - Oct 31
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 concierge services and access to locker space. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
Free Cancellation
Reserve now, pay when you stay
28 mi from city center
$149 nightly
The price is $166 total per night
$166 total
Oct 19 - Oct 20
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 luggage storage, securing valuables, and tours or tickets. Other amenities at this ski condominium resort include 2 hot tubs, outdoor tennis courts, and free WiFi in public areas.
Pool
Hot Tub
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd, Williamstown, MA
29.46 mi from city center
$347 nightly
The price is $388 total per night
$388 total
Oct 17 - Oct 18
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
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
12.82 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. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
The Kemble- Built by a US Secretary of State in Lenox

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

14.65 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, a garden, and barbecue grills.
Kitchen
Washer
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

13.65 mi from city center
At this vacation home, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

27.36 mi from city center
$969 nightly
The price is $1,047 total per night
$1,047 total
Oct 21 - Oct 22
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
Peace and quiet on the lake

Peace and quiet on the lake

7.41 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

27.75 mi from city center
$478 nightly
The price is $485 total per night
$485 total
Oct 16 - Oct 17
Total with taxes and fees
This vacation home offers a gym, a sauna, and a hot tub. Additional amenities include an arcade/game room, laundry facilities, and a garden.
Pool
Hot Tub
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

15.76 mi from city center
$640 nightly
The price is $715 total per night
$715 total
Oct 26 - Oct 27
Total with taxes and fees
Guests staying at this cabin have access to a garden and barbecue grills.
Kitchen
Pet friendly
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

5.3 mi from city center
Guests staying at this cottage can enjoy a gym, a garden, and barbecue grills.
Kitchen
Pet friendly
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

22.64 mi from city center
At this vacation home, guests have access to free WiFi in public areas, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, a garden, and barbecue grills.
Hot Tub
Kitchen
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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.

The Berkshires Large Group Rentals

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 $125 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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