Vacation rentals in Berkshire County

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

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
$126 nightly
The price is $141 total per night
$141 total
Jan 13 - Jan 14
Total with 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
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
9.06 mi from city center
$166 nightly
The price is $186 total per night
$186 total
Jan 20 - Jan 21
Total with 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
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
$208 nightly
The price is $233 total per night
$233 total
Jan 14 - Jan 15
Total with 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
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
Get rates
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 terrace and laundry facilities.
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

Lenox MA
6.77 mi from city center
Get rates
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
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

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

Great Barrington MA
18.47 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA
15.08 mi from city center
$253 nightly
The price is $283 total per night
$283 total
Jan 24 - Jan 25
Total with taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA
3.72 mi from city center
Get rates
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
16.91 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Hancock MA
7.39 mi from city center
Get rates
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room. A gym and a hot tub are also provided.
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
9.46 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
5 Minutes from Catamount Ski Area

5 Minutes from Catamount Ski Area

Egremont MA
21.71 mi from city center
Get rates
A hot tub is featured at this vacation home, along with a garden.
Hot Tub
Kitchen
The Greylock Cabin

The Greylock Cabin

Florida MA
21.49 mi from city center
$369 nightly
The price is $399 total per night
$399 total
Feb 8 - Feb 9
Total with taxes and fees
This vacation home features laundry facilities.
Kitchen
Washer
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock MA
7.34 mi from city center
$247 nightly
The price is $276 total per night
$276 total
Jan 13 - Jan 14
Total with taxes and fees
Ski-in/ski-out access and an indoor pool are featured at this smoke-free apartment. A gym and a hot tub are also provided.
Pool
Hot Tub
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis MA
22.86 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.
Kitchen
Washer
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough MA
19.65 mi from city center
Get rates
A gym is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
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
7.11 mi from city center
Get rates
An outdoor pool is featured at this vacation home, along with laundry facilities and barbecue grills.
Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town

Lenox MA
6.62 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Berkshire County
View all properties
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 $141 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.