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Our top choices for The Berkshires cottages
1. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck3.0 star property
Stephentown
$529 nightly
The price is $587
$587 total
Nov 9 - Nov 10
Total with taxes and fees
2. Waterfront Lake Cottage - Lake Access -Kayaks
Waterfront Lake Cottage - Lake Access -KayaksAvon
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
"The cottage is very cozy, private, and in a beatiful setting. We really appreciated the upgrades that made our stay comfortable. The fenced-in yard was great for our dog. Take a note of a stone floor on the lower level. We had to cover it to be not too cold for the dog to lie on (in late October). The location is right on the water for kayaking and close to some well maintained trails for biking and hiking."
"The cottage is very cozy, private, and in a beatiful setting. We really appreciated the upgrades that made our stay comfortable. The fenced-in yard was great for our dog. Take a note of a stone floor on the lower level. We had to cover it to be not too cold for the dog to lie on (in late October). The location is right on the water for kayaking and close to some well maintained trails for biking and hiking."
Victoria F.
$497 nightly
The price is $568
$568 total
Dec 8 - Dec 9
Total with taxes and fees
3. Sharon Retreat w/ Private Yard
Sharon Retreat w/ Private YardSharon
9.2 out of 10, Wonderful, (37 reviews)
9.2/10
Wonderful
(37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"Heidi F.
$396 nightly
The price is $453
$453 total
Nov 9 - Nov 10
Total with taxes and fees
4. Berkshires farm, 30+ guests, 50 acres
Berkshires farm, 30+ guests, 50 acresNew Lebanon
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
$1,850 nightly
The price is $1,862
$1,862 total
Nov 18 - Nov 19
Total with taxes and fees
5. The Cottage on Mill Brook is walking distance to Berkshire East and the River.
The Cottage on Mill Brook is walking distance to Berkshire East and the River.Charlemont
$540 nightly
The price is $603
$603 total
Nov 13 - Nov 14
Total with taxes and fees
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.
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.
Learn more about The Berkshires
Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.
Photo by Photo courtesy of Berkshire Visitors Bureau
Open Photo by Photo courtesy of Berkshire Visitors Bureau
Top reviews in The Berkshires
Prospect Berkshires
Prospect BerkshiresEgremont
10/10 Excellent
So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
Emily
Devonfield Inn B&B
Devonfield Inn B&BLee
10/10 Excellent
The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!
The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!
Anonymous traveler
Vikings Villages Resort
Vikings Villages ResortGuilford
10/10 Excellent
I would leave all my possessions behind to live in this cabin forever.
I would leave all my possessions behind to live in this cabin forever.
Diego
Howard Hotel
Howard HotelHudson
10/10 Excellent
Wonderful hotel
Wonderful hotel
zehava
Hotel On North
Hotel On NorthPittsfield
10/10 Excellent
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
Steve
Wilder House Berkshires
Wilder House BerkshiresSheffield
10/10 Excellent
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.
Liliana
Harbour House Inn
Harbour House InnCheshire
10/10 Excellent
The Harbor House Inn is a wonderfully situated B and B, located 8 miles south of North Adams. The welcome is warm, and amenities are generous. Highly recommended.
The Harbor House Inn is a wonderfully situated B and B, located 8 miles south of North Adams. The welcome is warm, and amenities are generous. Highly recommended.
Anonymous traveler
Shaker Mill Inn
Shaker Mill InnWest Stockbridge
10/10 Excellent
This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...
This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...
Joe
East Rock Inn
East Rock InnGreat Barrington
10/10 Excellent
Great room, recently renovated. Very close to Butternut and other areas of interest.
Great room, recently renovated. Very close to Butternut and other areas of interest.
Heather
The Williams Inn
The Williams InnWilliamstown
10/10 Excellent
Beautiful
Beautiful
Peter
The Inn at Stockbridge
The Inn at StockbridgeStockbridge
10/10 Excellent
Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts.
The new owners have added new touches to this Inn and the pride of ownership shows.
Highly recommended 👌
Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts.
The new owners have added new touches to this Inn and the pride of ownership shows.
Highly recommended 👌
Kevin
Brook Farm Inn
Brook Farm InnLenox
10/10 Excellent
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
roberta
Chambery Inn
Chambery InnLee
10/10 Excellent
The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls.
Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance.
The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls.
Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance.
Elaine
Maple Terrace Motel
Maple Terrace MotelWilliamstown
10/10 Excellent
Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates.
Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates.
Eric
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
10/10 Excellent
We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!
We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!
Anonymous traveler
Frequently Asked Questions
How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between $452 and $1,861 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 cottages in The Berkshires and then select your favorite. Whether you're organizing a vacation 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 Center, 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.