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
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $145 total per night
$145 total
Aug 27 - Aug 28
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
$159 nightly
The price is $178 total per night
$178 total
Sep 1 - Sep 2
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 securing valuables, luggage storage, 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
$88 nightly
The price is $99 total per night
$99 total
Sep 3 - Sep 4
Total includes 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
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
The Kemble- Built by a US Secretary of State in Lenox

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

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
Peace and quiet on the lake

Peace and quiet on the lake

Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

$968 nightly
The price is $1,046 total per night
$1,046 total
Aug 25 - Aug 26
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
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

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

At this cabin, guests have access to in-room fitness, laundry facilities, and barbecue grills. This smoke-free cabin also has a garden.
Kitchen
Washer
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

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, barbecue grills, and a garden.
Hot Tub
Kitchen
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

At this cabin, guests have access to features like laundry facilities. Friendly staff can provide concierge services, and also offer advice about sightseeing. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
Florida Mountain Log Cabin!

Florida Mountain Log Cabin!

2 out of 5
$399 nightly
The price is $422 total per night
$422 total
Sep 3 - Sep 4
Total includes taxes and fees
At this cabin, guests have access to barbecue grills.
Kitchen
Air conditioning
Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town

Guests staying at this vacation home have access to 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!

Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

At this vacation home, guests have access to a garden.
Air conditioning
Outdoor Space
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

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
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

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
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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

    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    $86 nightly
    The price is $96 total per night from Sep 8 to Sep 9
    $96 total
    Sep 8 - Sep 9
    Total includes taxes and fees
    8.8/10 Excellent! (572 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $130 nightly
    The price is $145 total per night from Aug 27 to Aug 28
    $145 total
    Aug 27 - Aug 28
    Total includes taxes and fees
    8.6/10 Excellent! (1,956 reviews)
    Quality Inn

    Quality Inn

    372 Main Street, Rte 7 and Main Street, Great Barrington, MA
    $93 nightly
    The price is $104 total per night from Sep 2 to Sep 3
    $104 total
    Sep 2 - Sep 3
    Total includes taxes and fees
    8.2/10 Very Good! (1,008 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 $96 and $1,046 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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