Compare Western Massachusetts Vacation Rentals

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Western Massachusetts 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
25.8 mi from city center
$120 nightly
The price is $134 total per night
$134 total
Aug 4 - Aug 5
Total includes 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
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
25.68 mi from city center
$179 nightly
The price is $200 total per night
$200 total
Jul 24 - Jul 25
Total includes 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 concierge services. Other amenities at this ski condominium resort include outdoor tennis courts, free WiFi in public areas, and meeting rooms.
Pool
Parking included
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
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. 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 an outdoor tennis court.
Pool
Kitchen
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd, Williamstown, MA
27.65 mi from city center
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
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

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

17.1 mi from city center
$336 nightly
The price is $375 total per night
$375 total
Aug 11 - Aug 12
Total includes taxes and fees
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

28.65 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
PICON COZY

PICON COZY

24.38 mi from city center
$140 nightly
The price is $159 total per night
$159 total
Jul 28 - Jul 29
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Dryer
HOMEY HOMEY

HOMEY HOMEY

24.38 mi from city center
$147 nightly
The price is $167 total per night
$167 total
Jul 24 - Jul 25
Total includes taxes and fees
This apartment is a smoke-free apartment building.
Free WiFi
Air conditioning
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

28.53 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

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

25.66 mi from city center
$290 nightly
The price is $329 total per night
$329 total
Jul 31 - Aug 1
Total includes taxes and fees
This vacation home offers a water park, a gym, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
Kitchen
Washer
The Kemble- Built by a US Secretary of State in Lenox

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
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

26.35 mi from city center
$957 nightly
The price is $1,035 total per night
$1,035 total
Jul 28 - Jul 29
Total includes 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
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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

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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