Vacation rentals in The Berkshires

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Top vacation rentals in The Berkshires

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
28.42 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Nov 14 - Nov 15
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
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
28 mi from city center
$149 nightly
The price is $166 total per night
$166 total
Nov 13 - Nov 14
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.
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd, Williamstown, MA
29.46 mi from city center
$221 nightly
The price is $247 total per night
$247 total
Dec 12 - Dec 13
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
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
12.82 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.
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Great Barrington, MA
11.84 mi from city center
$253 nightly
The price is $283 total per night
$283 total
Nov 19 - Nov 20
Total with taxes and fees
A gym is featured at this vacation home, along with a garden and laundry facilities.
Kitchen
Washer
The Kemble- Built by a US Secretary of State in Lenox

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

14.65 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.
Peace and quiet on the lake

Peace and quiet on the lake

7.41 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

27.36 mi from city center
$1,026 nightly
The price is $1,111 total per night
$1,111 total
Nov 18 - Nov 19
Total with 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
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

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

13.65 mi from city center
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An outdoor pool is featured at this vacation home, along with laundry facilities and barbecue grills.
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

27.75 mi from city center
$533 nightly
The price is $540 total per night
$540 total
Nov 13 - Nov 14
Total with taxes and fees
This vacation home features a gym and a hot tub. Enjoy the sauna and conveniences like a garden and laundry facilities.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

22.64 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.
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

28.15 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.
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

15.69 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.
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington, MA
12.77 mi from city center
$1,193 nightly
The price is $1,332 total per night
$1,332 total
Nov 13 - Nov 14
Total with taxes and fees
This vacation home features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
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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 your Vacation Rentals in The Berkshires

How cheap can a vacation rental in The Berkshires be?

You can find vacation rentals in The Berkshires for as low as $133 per night.

How do you look for the best vacation rental deals in The Berkshires with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout The Berkshires so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in The Berkshires can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in The Berkshires?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our The Berkshires vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in The Berkshires?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, The Berkshires vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in The Berkshires?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom The Berkshires vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.