The Berkshires Cottages

A person snowboarding down a snowy slope.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for The Berkshires cottages

1. Mtn-view Retreat in Huson Valley: Great for Groups

Hudson

HK$5,977 total

includes taxes & fees

21 Aug - 22 Aug

2. Perfect for a peaceful get away in clean fresh Vermont air!

Woodford

Adam a.

HK$3,217 total

includes taxes & fees

31 Aug - 1 Sept

3. Berkshires farm, 30+ guests, 50 acres

New Lebanon

HK$16,994 total

includes taxes & fees

9 Sept - 10 Sept

4. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

HK$4,348 total

includes taxes & fees

24 Aug - 25 Aug

5. 3 Mi to Mount Snow: Spacious West Dover Home

West Dover

HK$5,128 total

includes taxes & fees

20 Aug - 21 Aug

View all properties

Find holiday rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"The room was clean and the beds comfortable. The bathroom was small but nice. Lots of construction in the parking areas but luckily we got a parking space. Staff was friendly and helpful. We ate at the hotel, the food was good."

The Yankee Inn

10/10 Excellent

"Seamless stay from check in to check out. All the important things like cleanliness and updated bathroom with working faucets, great shower, lots of towels, etc. and unusual amenities like “two” swimming pools as well as hiking (walking) trail and ponds in the rear of the hotel property. Breakfast offerings had a big variety of foods similar to other hotels that offer full breakfast buffets. Located on a business strip with supermarkets and other useful retail stores however the hotel sits back from the road so is fairly quiet especially at night. Our room had a wide covered balcony with Adirondack chairs. Small fire-pit area out in front of the man entrance. Personally, I would have preferred a softer bed but was not uncomfortable and it did not affect my sleep. Linens and pillows were very nice, fluffy, and very clean. No funky hotel odors in the room or halls. The staff was very friendly, polite and helpful. It shows that this facility makes every effort to run a great hotel and please their customers."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"Shower base was very slippery-dangerous. Air-conditioning controls were poor. Thermostat was difficult to adjust and there was no ability to direct the cold air from the fan away from directly blowing on the bed. Had to move furniture to block it. Everything else was fine."

Berkshires Untold

8/10 Good

"Lovely man at check in for our overnight ( to see Hugh Jackman at 7 pm at Tanglewood lucky us!👍 Checked that food would be available in their bar upon our trying as has driven 2+ hrs assured yes until just before 10 pm closing. Called once on way back at 9:10 for 10 min drive to dbl check as hungry. Woman said no, they stopping serving at 9... luckily she rec one place nearby which was still open for food til midnight! Wow in Lenox! Very packed loud and fun w locals & Jackman fans..got wines, friendly bartenders, ordered yummy plates of tacos , sandwich and ended eve on a great note . Go to OMBRA if hungry after 9! Small complaint this am also.. we ordered a bagel & a berry salad from the hotel's brkfst menu to go as needed to drive back home mid am.. Opened it and about 1/2 cup of mixed berries ..for $11.00... Think the bagel was 8. Oh well -worth the splurge to see Hugh 💕and only 10 min drive to Tanglewood & downtown Lenox! Hotel not walkable to anything but ez parking & very cute interior & bar & seating areas!"

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews	84
Accommodation	84 Cottages
Lowest Price	HK$3,217
Highest Price	HK$16,994

Frequently asked questions

How much do cottages in The Berkshires cost?

Prices for cottages in The Berkshires range between HK$3,217 and HK$16,994 per night. Whatever your budget, you'll find an ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in The Berkshires?

Explore our 84 cottages in The Berkshires and then select your favourite. Whether you're organising a holiday with the whole fam or a break with pals, your perfect stay is just a few clicks away with Expedia.

Why book your cottage in The Berkshires with Expedia?

Booking a cottage in The Berkshires is as easy as clicking on your travel dates and choosing an ideal place for outdoor fun and relaxation. From upmarket retreats to affordable stays and cottages that include perks like a hot tub, Expedia has something for all styles and tastes. As for the best deals around? We've got them too!

How can I find cheap cottages in The Berkshires?

The easiest way to compare cheap cottages in The Berkshires is with Expedia's user-friendly filter tool. Refine your search by budget, star rating and amenities to discover excellent rates with only a few clicks.

What is there to do in The Berkshires near my cottage?

One of the most important travel accessories for your The Berkshires trip is a good itinerary! Tanglewood Music Centre, Shakespeare and Company and The Mount are among the most popular sights if you're on your way to Lenox. Williamstown is also home to terrific attractions, such as Chapin Library of Rare Books and Manuscripts. In the mood to explore more? Carve out some time for Hopkins Observatory and Williams College Museum of Art too.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires cottages

1. Mtn-view Retreat in Huson Valley: Great for Groups

2. Perfect for a peaceful get away in clean fresh Vermont air!

3. Berkshires farm, 30+ guests, 50 acres

4. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

5. 3 Mi to Mount Snow: Spacious West Dover Home

Find holiday rentals that suit your style

Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Vacation Village in the Berkshires

The Yankee Inn

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Great Barrington

Jiminy Peak Mountain Resort

Berkshires Untold

Find out more about The Berkshires

The Berkshires Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Cottages in The Berkshires

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires cottages

1. Mtn-view Retreat in Huson Valley: Great for Groups

2. Perfect for a peaceful get away in clean fresh Vermont air!

3. Berkshires farm, 30+ guests, 50 acres

4. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

5. 3 Mi to Mount Snow: Spacious West Dover Home

Find holiday rentals that suit your style

Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about The Berkshires

The Berkshires Cottages information

Frequently asked questions

Explore a world of travel with Expedia