Photo by Photo courtesy of Berkshire Visitors Bureau

The Berkshires holiday rentals

We found 1,513 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – The Berkshires

Showing deals for:11 Dec - 18 Dec

Interior
Interior
Dining
Property grounds
Exceptional
(23 reviews)

Sunny Chalet Nestled in the Woods of Ashfield

Ashfield

16% off
AU$3,442
for 7 nights, 1 chalet
AU$492 per night
includes taxes & fees
Sunny Chalet Nestled in the Woods of Ashfield
Early morning summer view
View out front door
 Open Kitchen with a wide open feel
View from Kitchen sink
Exceptional
(243 reviews)

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

8% off
AU$6,985
for 7 nights, 1 home
AU$998 per night
includes taxes & fees
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Open kitchen to great room, wonderful for cooking and entertaining
The great room with wonderful water views and working fireplace
Dining
Sunroom has Queen pull out sofa bed
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
AU$6,421
for 7 nights, 1 home
AU$917 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
View of lake through window, table for 6 on right, 4 bar stools at counter
House facing lake with deck above, canoe and kayak stored on ground level.
Property grounds
Terrace/patio
Exceptional
(169 reviews)

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

Otis

16% off
AU$2,695
for 7 nights, 1 home
AU$385 per night
includes taxes & fees
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Workstation with a view!
view from the 2nd bedroom
View of the lower deck from the sunroom
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$6,783
for 7 nights, 1 home
AU$969 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Interior
Terrace/patio
Exterior
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

8% off
AU$3,395
for 7 nights, 1 cottage
AU$485 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Exterior
Private kitchen
Living area
Property grounds
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$5,173
for 7 nights, 1 home
AU$739 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Property grounds
Kitchen with counter seating for 4- door on the right to garage
Outdoor dining
Enclosed porch- view into back yard- dining/game table
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,253
for 7 nights, 1 home
AU$750 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Interior
Front showing deck on the side of the house in both levels
Looking towards outside deck and tiv area in fireplace sitting area
Kitchen island with 2 swivel chairs and pantry, and coat closet with barn doors
Exceptional
(133 reviews)

Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

8% off
AU$3,369
for 7 nights, 1 home
AU$481 per night
includes taxes & fees
Gorgeous Mountain Views Retreat: Family & Nature
Living area
Terrace/patio
Dining
Private kitchen
Exceptional
(20 reviews)

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

Williamstown

12% off
AU$4,051
for 7 nights, 1 cottage
AU$579 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Walk to Spring Street and brand new Williams Bookstore
Beautiful period woodwork and Victorian details
Build a cozy fire in our wood fireplace, watch the game or play pool!
Gourmet kitchen has everything you need to prepare delicious meals
Exceptional
(157 reviews)

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

Williamstown

7% off
AU$8,233
for 7 nights, 1 home
AU$1,176 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Front Staircase
Fully screened porch!
Reading nook with natural lighting
Dining Room w/ Doors to Screened Porch Dining Area
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
AU$4,210
for 7 nights, 1 home
AU$601 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Patio off kitchen
Kitchen
Cottage Entrance
Kitchen open to living room
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

Great Barrington

8% off
AU$2,280
for 7 nights, 1 cottage
AU$326 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Property grounds
Interior
Exterior
Dining
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,743
for 7 nights, 1 cabin
AU$535 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Exterior detail
Living area
Interior
Outdoor dining
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$5,835
for 7 nights, 1 home
AU$834 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Outdoor dining and grill on the 16' x 20' wooden deck.
You will love dining and working in this rich and colorful room
Staircase
The living room flows into the dining room.
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,835
for 7 nights, 1 home
AU$691 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Living area
Private kitchen
Living area
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

8% off
AU$8,989
for 7 nights, 1 home
AU$1,284 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Living area
Interior
Room
Interior
Exceptional
(41 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
AU$2,382
for 7 nights, 1 home
AU$340 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Exterior
Interior
Living area
Property grounds
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
AU$4,574
for 7 nights, 1 cabin
AU$653 per night
includes taxes & fees
Guesthouse Cabin vacation rentals in Berkshire County
Pool
Interior
Interior
Private kitchen
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,362
for 7 nights, 1 home
AU$623 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Property grounds
Outdoor dining
Dining
Interior
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

21% off
AU$5,369
for 7 nights, 1 home
AU$767 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Open kitchen area with bar seating, great for socializing while you meal prep.
Second story deck with lake views, dining table for 8, sitting area and grill
Living room with fireplace and forest views
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
AU$5,388
for 7 nights, 1 home
AU$770 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Private kitchen
Ultimate Relaxation!  The hot tub will be warm and waiting for your arrival
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Welcome Home!
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$3,983
for 7 nights, 1 home
AU$569 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Alfresco dining
River view from window
Great room river view
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
AU$3,499
for 7 nights, 1 home
AU$500 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting captivating The Berkshires

Take a holiday to The Berkshires and enjoy the area's entertainment, museums and opera. Well known for its baseball games, hiking and skiing, this scenic city won't disappoint. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around The Berkshires

Are you hoping to find attractions to visit during your stay? You'll be sure to enjoy The Berkshires for its hiking and skiing. Venture out of your cosy holiday rental and experience everything that makes The Berkshires a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Otis Ridge (3.2 mi / 5.1 km)
  • Ski Butternut (8.8 mi / 14.2 km)
  • Wyndhurst Golf & Club (13.6 mi / 21.9 km)
  • Kennedy Park (16.1 mi / 25.9 km)
  • Catamount Ski Area (16.8 mi / 27.1 km)
  • Bousquet Ski Area (18.4 mi / 29.6 km)

Exploring the natural features in The Berkshires

Whether you're an active traveller or just want to spend some time taking in the scenery, The Berkshires is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Lake Garfield (2.7 mi / 4.3 km)
  • Otis Reservoir (5.7 mi / 9.1 km)
  • Lake Buel (6.5 mi / 10.4 km)
  • Goose Pond Reservation (8.2 mi / 13.3 km)
  • Housatonic River (11 mi / 17.7 km)
  • Housatonic River Walk (11 mi / 17.7 km)

Transport options to and around The Berkshires

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 19.3 mi (31 km) from the city centre.

If you're travelling by train, make your way to Pittsfield Station or Pittsfield Intermodal Transportation Center and explore the city from there.

Frequently asked questions

What is the best area to stay in The Berkshires when booking a holiday home?
One of the most popular areas to find a The Berkshires holiday home is Hancock. When you lock in your Stayz holiday property, you'll enjoy having the whole place to yourself. So you don't have to share it with anyone apart from your group.
What is the most popular type of holiday home accommodation in The Berkshires?
The most sought-after types of holiday homes in The Berkshires are houses. After something a little different? Stayz has a variety of options to match our guests' needs, so you'll see holiday properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — get yours today.
How much does it cost to rent a holiday home in The Berkshires?
A number of things can affect what you'll pay for your holiday home in The Berkshires, such as the length of stay, type of property and season. Still, all of our holiday homes have one thing in common — incredible value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in The Berkshires?
The average price for a holiday home close to the beach in The Berkshires depends on when you're visiting the area and the size and style of property you want. Find prices easily on Stayz by entering your preferred travel dates. Then use the filters to select the number of bedrooms and amenities that you prefer, like a pool, air conditioning and WiFi.
What are popular home amenities in The Berkshires?
When it comes to home amenities that guests search for in The Berkshires, a microwave oven, a stovetop and a fridge are the most popular. With Stayz holiday homes, you'll find options to fit your style and taste, whether you're travelling with family members, friends or even pets.
Are there large group holiday homes in The Berkshires?
With 94 properties that can sleep 10 guests or more in The Berkshires, there's no need to leave anyone off your guest list. From fun family get-togethers to events like birthday parties and weddings, Stayz will help you find a large group home that fits the occasion.
What are the top attractions for families in The Berkshires?
There are lots of fun things to do and see with the family in The Berkshires, such as:
  • Bousquet Ski Area
  • Ski Butternut
  • Jiminy Peak Mountain Resort
Can I find two-bedroom holiday homes in The Berkshires?
Take your pick of 144 two-bedroom homes in The Berkshires. Give the kids the second room or fill it with a couple of your best buddies. There's a spot for whoever's lucky enough to come along for the ride.
Are there holiday homes with WiFi in The Berkshires?
Whether you'd like to keep up with the headlines, reply to emails or post a pic to social media, there are 205 holiday homes with WiFi in The Berkshires. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.
How old do you have to be to rent a holiday home in The Berkshires?
You'll need to check with the Berkshires holiday home you'd like on Stayz as age restrictions differ. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in The Berkshires for?
The length of time you can book a holiday home in The Berkshires depends on the property. Just enter your desired dates to display a list of options offering extended stays. With plenty of features such as laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get a perfect place to call your home away from home in The Berkshires.

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