Vacation rentals in Berkshire County

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Top cities to explore in Berkshire County

Williamstown featuring cafe lifestyle

Williamstown

Vacation Rentals
Williamstown

Top vacation rentals in Berkshire County

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
8 mi from city center
$130 nightly
The price is $145 total per night
$145 total
Aug 27 - Aug 28
Total includes taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
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
7.57 mi from city center
$159 nightly
The price is $178 total per night
$178 total
Sep 1 - Sep 2
Total includes taxes and fees
Ski-in/ski-out access, 2 restaurants, and 2 outdoor tennis courts are all featured at this smoke-free condo resort. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Enjoy the 2 hot tubs and perks like free self parking and free WiFi.
Pool
Hot Tub
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd, Williamstown, MA
9.06 mi from city center
$90 nightly
The price is $101 total per night
$101 total
Sep 3 - Sep 4
Total includes taxes and fees
An outdoor pool is featured at this campground, along with free self parking. WiFi in public areas is free. A picnic area is also provided.
Pool
Pet friendly
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
8.9 mi from city center
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This condo resort features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and conveniences like a 24-hour front desk and laundry facilities.
Pool
Kitchen
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

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

21.4 mi from city center
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In-room fitness is featured at this cabin, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
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

2.23 mi from city center
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A hot tub is featured at this vacation home, along with free WiFi in public areas and a garden. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

7 mi from city center
$968 nightly
The price is $1,046 total per night
$1,046 total
Aug 20 - Aug 21
Total includes taxes and fees
A hot tub is featured at this vacation home, along with a library and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.
Hot Tub
Kitchen
The Kemble- Built by a US Secretary of State in Lenox

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

6.77 mi from city center
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This villa features a gym and a sauna. Families will appreciate the arcade/game room and barbecue grills. A garden and laundry facilities are also provided.
Kitchen
Washer
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

17.32 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Peace and quiet on the lake

Peace and quiet on the lake

16.91 mi from city center
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This vacation home features a garden, laundry facilities, 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

3.87 mi from city center
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Laundry facilities, concierge services, and barbecue grills are available at this cabin.
Kitchen
Washer
Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town

6.62 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Florida Mountain Log Cabin!

Florida Mountain Log Cabin!

2 out of 5
20.35 mi from city center
$399 nightly
The price is $422 total per night
$422 total
Sep 3 - Sep 4
Total includes taxes and fees
This cabin features barbecue grills.
Kitchen
Air conditioning
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.05 mi from city center
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A garden is available at this vacation home.
Air conditioning
Outdoor Space
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

15.25 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

28.14 mi from city center
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A water park and a hot tub are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and childcare is an added bonus. There's a gym on site, and laundry facilities and barbecue grills are also offered.
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

8.02 mi from city center
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A hot tub is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
Hot Tub
Kitchen
Stay Lakeside This Summer!

Stay Lakeside This Summer!

15.61 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
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.

The Best Way to Find Vacation Rentals in Berkshire County 

How cheap is a vacation rental in Berkshire County?


You can find Berkshire County vacation rentals from just $101 per night. 


How do you look for the best vacation rental deals in Berkshire County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Berkshire County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Berkshire County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Berkshire County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Berkshire County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Berkshire County?


Whether you’re a winter wanderer or planning a summer sojourn, Berkshire County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Berkshire County?


Take your pick from the excitement of the big Berkshire County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Berkshire County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Berkshire County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.