Search Cottages in The Berkshires

Most properties are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Featured Cottages in The Berkshires and around

Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Property grounds
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Perfect Vacation Get Away - Historical New Marlborough
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is €258
includes taxes & fees
6 May - 7 May
Perfect Vacation Get Away - Historical New Marlborough
The Blue Elm - A Historic Berkshire Cottage
Exterior
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (2)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is €394
includes taxes & fees
23 May - 24 May
The Blue Elm - A Historic Berkshire Cottage
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Cozy Berkshire cottage with fireplace.
Fridge, microwave, oven, stovetop
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."
Cozy Berkshire cottage with fireplace.
Charming historic cottage on scenic road to Mt. Greylock
Property grounds
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (93)
"I had a wonderful time. The lil stone house school is restored in a loving way! It feels homie and cosy and has a lot of stories to tell. The location is great for seeing museums or just go for a hike. Rich and Cheryl are on top with everything and very nice hosts!"
Charming historic cottage on scenic road to Mt. Greylock
Charming unique cottage Relax & enjoy the stunning mountains with private views!
Exterior
Charming unique cottage Relax & enjoy the stunning mountains with private views!
10.0 out of 10, Exceptional, (17)
"We enjoyed our stay along with our dogs at the Gazebo. Beautiful mountain views and peaceful environment. Plenty of hiking and quiet country roads to walk the dogs. The cottage is very quaint and tastefully decorated. We hope to be back again."
Charming unique cottage Relax & enjoy the stunning mountains with private views!
Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (94)
"A very nice stay. Communication with the host was great. We kept bothering her with questions and she responded quickly. The place is really beautiful. We lit a fire each night and played some of the provided games and watched Netflix. It's an easy drive to Great Barrington to get groceries at the Berkshire coop. We also took advantage of our surroundings and hikes on the AT a little each day. Next time we'll use the host's canoe to explore Lake Buel. The only minor complaint I would have is...
Quiet rustic cottage with shared lake access
East Otis Vacation Rental w/ Private Deck & BBQ!
Desk, Internet, bed sheets
East Otis Vacation Rental w/ Private Deck & BBQ!
9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Dining
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (2)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Beachwood Cottage
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."
Beachwood Cottage
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Interior
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.5 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Spacious Historic Home in the Berkshires!
Interior
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Beautiful Berkshires Cottage on Lake Buel
Interior
Beautiful Berkshires Cottage on Lake Buel
Beautiful Berkshires Cottage on Lake Buel
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Outdoor dining
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.0 out of 10, Wonderful, (32)
"Quaint cabin tucked away in the Berkshires. For those vacationing with a pet, be aware that on Labor Day weekend this neighborhood puts on a fireworks show right by this house. Also, there really is not any yard, just a small patio. Lots of great hiking in the area."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
The Blue Jay - a New England Cottage
Fridge, microwave, oven, stovetop
The Blue Jay - a New England Cottage
9.8 out of 10, Exceptional, (6)
"The cabin was as advertised and super clean. We had a great time exploring the area."
The Blue Jay - a New England Cottage
Picturesque Cottage with Sunroom on Ashmere Lake!
View from property
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
"It was perfect for me and my close friends. We enjoyed the lake each day and all remarked that the beds were very comfortable. Wish we could have stayed longer."
Picturesque Cottage with Sunroom on Ashmere Lake!
Spacious & Modern Ashley Falls Home on 1 Acre
Interior
Spacious & Modern Ashley Falls Home on 1 Acre
3.5 star property
Spacious & Modern Ashley Falls Home on 1 Acre
Cottage in the Berkshires 10 min. to Great Barrington
Property grounds
Cottage in the Berkshires 10 min. to Great Barrington
Cottage in the Berkshires 10 min. to Great Barrington
Berkshires - Charming Lakefront Cottage
Property grounds
Berkshires - Charming Lakefront Cottage
10.0 out of 10, Exceptional, (1)
"We stayed for a week at Stacy and Bob's place. Communication was excellent ahead of time. The house was incredibly clean upon arrival and everything was just as listed. They even went above and beyond with a wonderful welcome basket. They even had a small first aid/medicine kit, "just in case." We truly enjoyed their place."
Berkshires - Charming Lakefront Cottage
Waterview Home in the Berkshires: Near Hiking
Interior
Waterview Home in the Berkshires: Near Hiking
3.0 star property
Waterview Home in the Berkshires: Near Hiking
Don't see what you're looking for?
See all available properties in The Berkshires
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.

Other property types in The Berkshires

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1672)
"Very nice spot quiet "
The price is €181
includes taxes & fees
5 May - 6 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
2 Bedroom Condo 1/2 mile from base | Private kitchen
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (856)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is €152
includes taxes & fees
5 May - 6 May
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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 Berkshires Cottages information

Number of reviews
317
Accommodation
72 Cottages
Lowest Price
Highest Price

Recent Reviews in The Berkshires
Expedia verified reviews

Life House Berkshires

Life House Berkshires

5/5 Excellent
"It’s the perfect place to go for a weekend or weeklong stay and be as isolated as social as you want. The towns nearby are fantastic. Will definitely be back a lot "
A verified traveller stayed at Life House Berkshires
Posted 3 days ago
Life House Berkshires