A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Berkshire County holiday rentals

We found 1,290 holiday rentals — enter your dates for availability

Select from 555 houses, 69 flats and other holiday rentals to find the perfect place for your stay in Berkshire County. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, including air conditioning and Wi-Fi. At the end of the day, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.

Popular Berkshire County destinations on Stayz

A large white colonial-style house with a stone foundation, a white fence, and a green lawn.

Lenox

A historic building with a clock, a flag, and a street lamp.

Pittsfield

A white church with a steeple, surrounded by autumn-colored trees.

Williamstown

A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.

Great Barrington

A calm lake reflecting a forest with autumn foliage.

Stockbridge

A historic street with brick buildings, storefronts, and parked cars.

Lee

Holiday rentals with weekly discounts – Berkshire County

Showing deals for:20 Nov - 27 Nov

Exceptional

(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

21% off

AU$5,426

for 7 nights, 1 home

AU$775 per night

includes taxes & fees

Exceptional

(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off

AU$3,942

for 7 nights, 1 home

AU$563 per night

includes taxes & fees

Exceptional

(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off

AU$4,873

for 7 nights, 1 home

AU$696 per night

includes taxes & fees

Exceptional

(5 reviews)

Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak

Hancock

20% off

AU$2,894

for 7 nights, 1 room

AU$413 per night

includes taxes & fees

Exceptional

(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off

AU$6,219

for 7 nights, 1 home

AU$888 per night

includes taxes & fees

Gourmet kitchen has everything you need to prepare delicious meals

Beautiful period woodwork and Victorian details

Build a cozy fire in our wood fireplace, watch the game or play pool!

Exceptional

(154 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off

AU$8,322

for 7 nights, 1 home

AU$1,189 per night

includes taxes & fees

Exceptional

(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off

AU$7,753

for 7 nights, 1 home

AU$1,108 per night

includes taxes & fees

Kitchen with counter seating for 4- door on the right to garage

Enclosed porch- view into back yard- dining/game table

Exceptional

(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off

AU$5,578

for 7 nights, 1 home

AU$797 per night

includes taxes & fees

Exceptional

(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off

AU$4,095

for 7 nights, 1 cottage

AU$585 per night

includes taxes & fees

Exceptional

(81 reviews)

Large Barn styled vacation home that fits groups with space to spare.

Craryville

8% off

AU$5,820

for 7 nights, 1 home

AU$831 per night

includes taxes & fees

Exceptional

(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off

AU$6,229

for 7 nights, 1 home

AU$890 per night

includes taxes & fees

Exceptional

(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off

AU$5,650

for 7 nights, 1 cabin

AU$807 per night

includes taxes & fees

Exceptional

(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off

AU$3,783

for 7 nights, 1 cabin

AU$540 per night

includes taxes & fees

Exceptional

(40 reviews)

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.

Stephentown

8% off

AU$2,407

for 7 nights, 1 home

AU$344 per night

includes taxes & fees

Flat screen Smart cable tv 5G network.
WiFi of course.

Exceptional

(191 reviews)

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Sheffield

8% off

AU$3,061

for 7 nights, 1 home

AU$437 per night

includes taxes & fees

The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided

Unwind and cherish moments together in the inviting warmth of the cozy living room.

Exceptional

(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off

AU$7,971

for 7 nights, 1 home

AU$1,139 per night

includes taxes & fees

Open plan dining area with water views and access to the sunroom

Exceptional

(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off

AU$6,856

for 7 nights, 1 home

AU$979 per night

includes taxes & fees

Exceptional

(10 reviews)

Lakefront +pets +skiing +bbq +firepit +games

Copake

8% off

AU$4,138

for 7 nights, 1 home

AU$591 per night

includes taxes & fees

You will love dining and working in this rich and colorful room

A mudroom off the back leads to the large wooden deck

The living room flows into the dining room.

Exceptional

(41 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off

AU$4,994

for 7 nights, 1 home

AU$713 per night

includes taxes & fees

Exceptional

(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

8% off

AU$4,372

for 7 nights, 1 home

AU$625 per night

includes taxes & fees

Exceptional

(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off

AU$3,503

for 7 nights, 1 home

AU$500 per night

includes taxes & fees

Exceptional

(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off

AU$3,536

for 7 nights, 1 home

AU$505 per night

includes taxes & fees

Exceptional

(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off

AU$5,381

for 7 nights, 1 home

AU$769 per night

includes taxes & fees

Living Room - Queen Sleep Sofa (First Floor)

Kitchen with Dining Area - well-equipped and great layout

Exceptional

(10 reviews)

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9% off

AU$4,032

for 7 nights, 1 home

AU$576 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Berkshire County

Vacation Village in the Berkshires

Sleeps 4

Premier Host

COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES

Sleeps 5 · 1 bedroom · 1 bathroom

Remote and Relaxing Cabin in the Berkshires

Sleeps 8 · 3 bedrooms · 2 bathrooms

Come to the Berkshires for outdoor enthusiast, or a relaxing couple retreat

Sleeps 6 · 2 bedrooms · 1 bathroom

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

Sleeps 40 · 13 bedrooms · 12+ bathrooms

Premier Host

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

Sleeps 9 · 4 bedrooms · 3 bathrooms

Top rated rentals - Berkshire County

Image of Spacious waterfront Berkshire home family private get-away

Premier Host

Lakeside in the Berkshires

This home was perfect for our family over the thanksgiving weekend. It has three levels and that provided privacy while the living area was open. Very clean, comfortable beds, a well stocked kitchen and good location for exploring Stockbridge and Lenox. Hiking trails and canoeing made it great for activities. The owner communicated answering questions promptly and left simple instructions for the home. Loved staying here.

Donna M.

Stayed Nov 2024

Choose a holiday rental for your Berkshire County getaway

Learn about the unique charm of Berkshire County with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Berkshire County

Are you hoping to discover attractions to see in the area? Venture out of your holiday home and experience everything that Berkshire County has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Bousquet Ski Area (2.7 mi / 4.3 km)
Kennedy Park (5 mi / 8.1 km)
Jiminy Peak Mountain Resort (7.4 mi / 11.9 km)
Furnace Brook Winery at Hilltop Orchards (7.5 mi / 12 km)
Wyndhurst Golf & Club (7.5 mi / 12 km)
Waubeeka Golf Links (14.3 mi / 22.9 km)

Exploring the natural landscape of Berkshire County

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Berkshire County is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

Onota Lake (1.7 mi / 2.8 km)
Pontoosuc Lake (3.2 mi / 5.1 km)
Lenox Mountain (4.2 mi / 6.7 km)
Kennedy Park (5 mi / 8.1 km)
Mount Greylock State Reservation Visitor Center (7.5 mi / 12 km)
Wahconah Falls State Park (7.8 mi / 12.6 km)

Transport to and around Berkshire County

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 2.4 mi (3.9 km) from the city centre.

If you prefer train travel, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.

Frequently asked questions

What is the best area to stay in Berkshire County when booking a holiday home?

If you're organising a Berkshire County escape, Hancock is one of the most desirable places to stay. Whether you choose a cottage, villa or another style of property, you'll always have the entire place to yourself.

What is the most popular type of holiday home accommodation in Berkshire County?

Based on our data, houses are the most in-demand holiday property type in Berkshire County. But having said that, everyone's idea of an awesome trip can vary. Stayz has holiday homes with every size, shape and budget in mind, and we'll help you to find the perfect match.

How much does it cost to rent a holiday home in Berkshire County?

A range of things can affect how much you pay for a holiday home in Berkshire County, including the time of year, property type and length of stay. Still, all Stayz homes have something in common — unbeatable value. Just add your travel dates to find your dream escape.

How much does it cost to rent a beach house in Berkshire County?

When you travel and the style and size of the property will determine the cost of your beachside escape. Click on your Berkshire County travel dates to see all your options on Stayz. Can't live without a private pool? Use the filters to pick the amenities and features you need.

What are popular home amenities in Berkshire County?

A fridge, a stovetop and a microwave oven head the list of most popular home amenities in Berkshire County. Whether you plan to travel by yourself, with your sweetheart or a group of family members, Stayz will help you find a holiday home that fits your style with all the features you're looking for.

Are there large group holiday homes in Berkshire County?

Berkshire County has 119 holiday homes that can fit 10 or more people. These stays come with the space you need to share good times with your favourite people.

What are the top attractions for families in Berkshire County?

You'll find loads of fabulous things to see and do with the family in Berkshire County, including:

National Shrine of the Divine Mercy
Tanglewood Music Centre
Jiminy Peak Mountain Resort

Can I find two-bedroom holiday homes in Berkshire County?

Gather your besties and enjoy peace, privacy and comfort in one of the 167 two-bedroom holiday properties Berkshire County has to offer.

Are there holiday homes with WiFi in Berkshire County?

Berkshire County has 260 holiday homes with WiFi, so you can stay connected during your holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Stayz homes make it a cinch to get online.

How old do you have to be to rent a holiday home in Berkshire County?

The minimum age requirements can differ across properties on Stayz, so check the rules of the holiday home in Berkshire County you're interested in. But normally, it's 16, 18 or 21.

How long can I rent a holiday home in Berkshire County for?

The amount of time you can rent a Berkshire County holiday home for depends on each property. Simply tap in your travel dates to browse available options offering longer term stays. They have all you need to make your extended holiday more convenient and enjoyable, such as kitchens and air conditioning. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.

More holiday ideas

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