Berkshire County Vacation Rentals

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Top cities in Berkshire County

Williamstown featuring cafe lifestyle
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Williamstown

Williamstown
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Stockbridge

Stockbridge

Berkshire County Vacation Rentals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
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
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
$188 nightly
The price is $211 total per night
$211 total
Jan 5 - Jan 6, 2026
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
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd Hancock MA
$193 nightly
The price is $216 total per night
$216 total
Jan 11 - Jan 12, 2026
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 concierge services, securing valuables, and luggage storage. Other amenities at this ski condominium resort include 2 hot tubs, outdoor tennis courts, and free WiFi in public areas.
Pool
Hot Tub
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
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
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Great Barrington MA
$249 nightly
The price is $278 total per night
$278 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
At this vacation home, guests have access to an arcade/game room, laundry facilities, and a garden.
Kitchen
Washer
Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
Guests staying at this vacation home have access to laundry facilities, 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

Lenox MA
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!

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

Great Barrington MA
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

Hancock MA
$715 nightly
The price is $725 total per night
$725 total
Dec 23 - Dec 24
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
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Lenox MA
At this vacation home, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

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

Great Barrington MA
Guests staying at this vacation home enjoy access to ski-in/ski-out access, a gym, and a hot tub. Other amenities at this ski vacation home include an arcade/game room, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock MA
$970 nightly
The price is $1,049 total per night
$1,049 total
Jan 6 - Jan 7, 2026
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
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

Pittsfield MA
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
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
Guests staying at this vacation home enjoy access to a water park, a gym, and a hot tub. Transportation is made easy with limo/town car service. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
Hot Tub
Kitchen
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Hancock MA
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills. This family-friendly vacation home also has a garden.
Hot Tub
Kitchen
The Greylock Cabin

The Greylock Cabin

Florida MA
$373 nightly
The price is $403 total per night
$403 total
Dec 23 - Dec 24
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2 out of 5
Florida MA
$316 nightly
The price is $339 total per night
$339 total
Dec 23 - Dec 24
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
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.

Hotel Options in Berkshire County

    The Williams Inn

    The Williams Inn

    101 Spring Street Williamstown MA
    $186 nightly
    The price is $208 total per night from Dec 22 to Dec 23
    $208 total
    Dec 22 - Dec 23
    Total with taxes and fees
    9.6/10 Exceptional! (549 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $126 nightly
    The price is $141 total per night from Jan 4 to Jan 5
    $141 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.6/10 Excellent! (2,174 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $93 nightly
    The price is $104 total per night from Dec 22 to Dec 23
    $104 total
    Dec 22 - Dec 23
    Total with taxes and fees
    8/10 Very Good! (988 reviews)

Orbitz makes it easy to find vacation rentals in Berkshire County 

🏠 What is the best price for a Berkshire County vacation rental?


Berkshire County rentals range between $104 and $1,049 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Berkshire County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Berkshire County getaway. Orbitz filters your search results so you can find the best Berkshire County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Berkshire County vacation rentals with Orbitz?


You may be able to cancel or amend your Berkshire County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Berkshire County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Berkshire County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Berkshire County?


When you book a Berkshire County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Berkshire County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Berkshire County—with plenty of hidden gems. We also have plenty of inventory in Berkshire County main cities and near popular attraction spots.


🏠 Why should I book my Berkshire County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Berkshire County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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