Cottage vacation rentals in Berkshire County

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Popular amenities for Berkshire County cottage rentals

Cottage rentals with a hot tub

Top guest favorite
A well-lit living area features a cozy sofa facing a coffee table on a colorful area rug. An open kitchen with modern appliances is visible in the background, alongside a dining table with four chairs. Decorative wall art adds character to the space.
Cottage in Lanesborough
5 out of 5 average rating, 20 reviews

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak

CherylRating, 5 stars3 weeks ago
One of the most clean air bnb I have stayed in. It was spotless and comfortable. The hot tub and kayaks were easy to use and just a few yards walk to the water. I would not change anything about this house. And thank you Darcy for being such a great host!
A hot tub is illuminated by bright lights during nighttime, surrounded by a snowy landscape. Nearby, outdoor seating and a heating lamp are visible, creating a cozy atmosphere. The main house stands in the background, framed by trees.
Cottage in Monterey
4.68 out of 5 average rating, 19 reviews

mountain refuge

JoshuaRating, 5 stars4 months ago
My girlfriend and I had a great time staying at Joktan’s place. We really enjoyed the home as well as the amenities that came with it. Joktan, provided excellent communication. Would recommend staying here!
Superhost
A sunroom features large glass windows offering views of vibrant autumn foliage. A futon couch adorned with colorful cushions is positioned alongside a wooden floor, inviting a relaxing atmosphere. Seasonal leaves are visible on the glass, gently filtering light into the space.
Cottage in Becket
4.65 out of 5 average rating, 164 reviews

A Magical Spot on Little Robin Lake

SebastianRating, 5 stars8 months ago
Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.
Top guest favorite
A bright, open living area features large glass sliding doors that overlook the lake. A dining table surrounds by chairs is set in the foreground, with a comfortable seating area visible to the right. Bookshelves and a decorative rug add warmth to the space.
Cottage in Otis
4.98 out of 5 average rating, 55 reviews

Berkshire lakefront cabin with modern luxuries

AileenRating, 5 stars1 week ago
We had a wonderful time! The house is beautiful in a spectacular spot on the lake. We were four adults and a large dog and had enough space. We got to use the kayaks/paddle board and fished endless hours from the dock The kitchen is well equipped and we cooked all our meals at the house I highly recommend this place and would come back if the opportunity arises
A spacious living area features light wood beams and large windows allowing natural light to fill the room. A cozy seating arrangement includes a green sofa, a rattan chair, and a plush rug. Bookshelves line one wall, filled with an array of books.
Cottage in New Marlborough

Light-filled cottage on a picturesque dirt road

Pet-friendly cottage rentals

Top guest favorite
A modern kitchen is equipped with stainless steel appliances and wooden cabinetry, complemented by light hardwood flooring. A rustic table with a fruit bowl is surrounded by four wooden chairs. A glass door provides access to the outdoor deck, allowing natural light to fill the space.
Cottage in Lee
4.99 out of 5 average rating, 103 reviews

Charming Home in Lee

AmyRating, 5 stars3 months ago
I think this was our fifth stay at Laurie's place, which shows how much we like it. It's perfect when we visit with family, because there is plenty of space for everyone. We didn't really take advantage of it this time, but having the full kitchen is nice. We're usually there in the winter, but one day I hope to be able to enjoy the porch and the deck.
Top guest favorite
A charming cottage is set amidst trees, featuring a stone and brick exterior. A welcoming front porch with seating offers views of Shaw Pond, visible through green foliage. The well-maintained yard provides a peaceful atmosphere, ideal for enjoying the surrounding natural beauty.
Cottage in Becket
5 out of 5 average rating, 25 reviews

Cheerful 3+ bedroom cottage with lake views

ScottRating, 5 stars8 months ago
This place was an excellent location for basing our trip to the Berkshires. We liked looking out over the lake, and walking around the community.
Guest favorite
The rustic carriage house is surrounded by lush greenery, featuring a vibrant garden with various plants and flowers. A teal umbrella provides shade over an outdoor seating area, complemented by a stone pathway leading to the entrance, enhancing the inviting atmosphere of the setting.
Cottage in Great Barrington
4.92 out of 5 average rating, 89 reviews

Carriage house with Chef's Kitchen, close to town

AnnRating, 5 stars1 week ago
Rachel’s carriage house is a charming and beautifully maintained property—just as described and shown in the photos. Even though the weather wasn’t ideal during our stay, we thoroughly enjoyed cozying up and relaxing in the warm, inviting space. One of our favorite features was the natural light streaming through the tall paned windows in the kitchen and dining area, overlooking the garden—a perfect setting for our morning coffee. The carriage house was thoughtfully stocked with everything we needed for a comfortable and restful getaway. It’s clear that Rachel has put a lot of care into creating a welcoming experience for her guests. We truly enjoyed our time in the Berkshires and would happily return!
Guest favorite
A two-story lodge is nestled among tall trees, with a babbling brook flowing in the foreground. The exterior is a rich brown wood, complemented by green foliage and rocks near the water. A small balcony is visible on the second floor, enhancing the picturesque setting.
Cottage in Austerlitz
4.93 out of 5 average rating, 88 reviews

Harvey Mountain Lodge by State Forest

LauraRating, 5 stars2 weeks ago
Lisa’s place was wonderful, and I highly recommend it. She was very responsive to questions, and I appreciated the helpful notes around the house. The space was thoughtfully made dog-friendly, with couch covers that kept things worry-free. The garden was beautiful, and the property offered great outdoor spaces—a back deck, a front grill with seating, and a creekside trail (not fully cleared, but enjoyable). My dog and I loved it. We stayed on the top floor and loved the airy living room with high ceilings and skylights. Lisa’s nature-inspired decor on the desk and fireplace mantle added charm. The bedroom was spacious, and the extra-large bed was incredibly comfortable. The house having three bathrooms was a nice bonus.
Superhost
A warm living room features a brown leather sofa positioned against a wooden accent wall. Two lamps with light blue bases provide soft lighting on either side. A simple wooden coffee table rests in front, with light streaming through two windows on either side.
Cottage in Hancock
4.83 out of 5 average rating, 84 reviews

Berkshire Cottage Queen Bd-Jiminy Peak 3 mi

KellyRating, 5 stars2 weeks ago
Renee was always responsive when we messaged. The Airbnb was super clean and the bed was very comfortable. Check in was so easy! At the end all Renee asked of us is to take the trash out which was super easy. I would definitely recommend this place. It is an especially good location for people who are attending a wedding at Bloom Meadows which is about 2 minutes away.
Guest favorite
A spacious living area is highlighted by exposed wooden beams and hardwood flooring. A large sectional sofa faces a rustic fireplace, which is surrounded by logs. Natural light enters through multiple windows, illuminating the cozy ambiance.
Cottage in Becket
4.78 out of 5 average rating, 165 reviews

Tranquil Lake Cottage on 3 Acres with Large Deck

DavidRating, 5 stars1 month ago
Enjoy your stay at this beautiful home. Looking for a get away from everyone this is the place to stay. House was perfect when we arrived and everything was smooth and simple from start to finish!
Guest favorite
A charming single-story home is surrounded by lush greenery and trees. A wooden deck with seating is positioned in front of the house, complemented by a stone chimney. Flowering shrubs frame the entrance, enhancing the inviting outdoor space.
Cottage in New Marlborough
4.9 out of 5 average rating, 39 reviews

Pet friendly Cottage on Lake; Hike, Swim, Kayak

KunalRating, 5 stars2 months ago
Loved the quick weekend getaway from the city! Wanted somewhere we could stretch out into.. which Ayren’s house fully is.. loved playing the many board games provided and watching movies in the late evenings.. plus a few walks down to the lake and drive to town which is less than 15 min away.. A very communicative host with clear instructions and well laid out amenities and basic kitchen condiments.. Thanks again for a great weekend !
Top guest favorite
A modern cottage is set against a backdrop of lush greenery. The exterior features dark siding, white-framed windows, and a prominent brick chimney. A potted plant adds a touch of color near the entrance, while the surrounding yard includes well-maintained grass and flowering shrubs.
Cottage in Monterey
4.96 out of 5 average rating, 25 reviews

New! Fully renovated private cottage

FrancesRating, 5 stars2 weeks ago
Nicely appointed and updated cottage for a quiet weekend get-away. The hosts think of everything, in terms of supplies, kitchen set-up, and nice decor. I couldn’t find a kitchen item and it was delivered quickly, which was very thoughtful. Bed was super comfy and the a/c window units came in handy! A little bit of road noise during the day, but it’s not bothersome. Wish I’d been there in a season to enjoy the local town beach, which looked nice. Definitely recommend!

Private cottage rentals

Guest favorite
A charming cottage is set among tall trees, featuring large windows that provide ample natural light. A spacious deck extends from the structure, complemented by outdoor seating options. The surrounding lush grass invites relaxation in a tranquil, wooded environment.
Cottage in Canaan
4.9 out of 5 average rating, 136 reviews

Plan your Berkshires by the lake

PattyRating, 5 stars4 weeks ago
I cannot emphasize enough how responsive, helpful and accommodating Julie was before and during our stay. The property is as shown, interior was clean and beds very comfortable. The walk to the lake is a short, peaceful one. It is a lovely setting with quiet neighbors. Highly recommend for anyone visiting nearby Berkshire attractions or for a quiet getaway near a beautiful lake!
A serene lakeside view captures a sunset reflected on tranquil waters. Soft pink and orange hues are visible among dark clouds in the sky, while the calm lake's surface mirrors the colors. A distant tree line borders the horizon, enhancing the peaceful ambiance.
Cottage in Hinsdale
4.69 out of 5 average rating, 64 reviews

Berkshire Cottage - Relaxation Destination

BlancaRating, 5 stars8 months ago
Jane's cabin was just as described. peaceful location with beautiful views.
A wooden dock extends into the calm water of a lake, surrounded by lush greenery and wooded hills. The tranquil scene is complemented by a cloudy sky reflecting soft light over the water, creating a serene ambiance.
Cottage in Monterey
4.79 out of 5 average rating, 14 reviews

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

PaulRating, 5 stars10 months ago
The cottage is clean and comfortable and the kitchen is well stocked. This is a nice place to serve as home base to explore all that the Berkshires have to offer.
A private cottage is nestled amid lush greenery, featuring a multi-level design with large windows and a spacious deck. The surrounding landscape is characterized by trees and grass, providing a natural and serene atmosphere.
Cottage in West Stockbridge
4.97 out of 5 average rating, 34 reviews

Tanglewood Cottage in the heart of the Berkshires

LuRating, 5 stars10 months ago
This was our second stay here, and we will hope to be back again next year. Less than three miles from Tanglewood, plus nearby hiking trails & historic sites, the location gave us plenty to do. The home is sparkling clean, has lots of towels, pillows, etc. Screened porch, deck, heat & AC if needed. Barred owls call during the night. Hosts live next door beyond the trees. Excellent communication if needed.
Guest favorite
A bright living area is featured, showcasing large windows that provide views of the surrounding nature. A fireplace is positioned centrally, complemented by a light-toned wooden sofa and a cozy chair. A dining table for two is visible, along with a small shelf and potted plants.
Cottage in Great Barrington
4.94 out of 5 average rating, 136 reviews

The Cottage at The Barrington House

EdwardRating, 5 stars1 day ago
Katie's home in Great Barrington was a lovely cottage nestled among greenery. We appreciated its cozy and modern design and very nice details like the Aesop soap. The location was very central in the Berkshires area. Just a short drive to Stockbridge main street, and a nice 15 minute drive to Tanglewood. Katie sent detailed instructions making it easy to find and enter the house and responded quickly to questions. The cottage is close to the main house, but it was very private inside with the landscaping around and excellent shades. The residential road definitely made it feel like a weekend in the country.
Guest favorite
A rustic cottage is surrounded by trees, featuring a deck with several chairs and a table. Warm light glows from the windows, illuminating the interior. The natural setting provides a tranquil atmosphere, inviting relaxation and connection with nature.
Cottage in Stockbridge
5 out of 5 average rating, 17 reviews

Rustic Berkshires Cottage

HannahRating, 5 stars11 months ago
Lovely cottage in the heart of the Berkshires. Well-stocked with anything you could need (kitchen utensils, chairs and toys for the lake, etc), comfy beds, and great location (a short walk to the public beach at the Stockbridge Bowl, and a short drive to Lenox, Stockbridge, Tanglewood and more). We loved sitting on the quiet porch in the evening. A great place for kids—loads of toys and games and swimming nearby.
Guest favorite
The image captures a broad view of a working vegetable farm, with multiple greenhouses visible in the foreground. Lush green fields stretch out towards the horizon, framed by distant hills under a clear blue sky. A winding path leads through the vibrant landscape.
Cottage in Great Barrington
4.98 out of 5 average rating, 128 reviews

Newly built cottage on working farm

StacyRating, 5 stars13 months ago
I had a wonderful retreat at this cottage – it’s a true GEM!! The photos don’t do it justice – it actually feels larger and the view is amazing. Having stayed in numerous rentals, I also want to give 2 thumbs-up to the thoughtful layout of the space and attention to detail (hooks where you need them, great lighting, etc.). The bed is comfy as are the couches, and it’s clean. Elizabeth and Al are available if needed, but totally give you space. And it’s deliciously quiet. Walking on the farm was a treat – watching the veggies and tulips grow over the week I visited. I can’t wait to return!
The kitchen is equipped with modern appliances, including a stove and microwave. White cabinetry contrasts with a light grey countertop. A large window offers a view of the outdoors, while natural light illuminates the space. A rug adds warmth to the tile floor.
Cottage in Stockbridge
5 out of 5 average rating, 4 reviews

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

MarilynRating, 5 stars5 months ago
We had a lovely visit! The house is immaculate and well stocked with everything we needed. The weather was cold and snowy, so we couldn't explore the grounds. But the fireplace was wonderful! We enjoyed the view from the deck, and would love to come back in the spring. The hosts were friendly and helpful. They delivered salt to us, and shoveled the walkways and driveway. You can't go wrong with this house. It's just perfect.

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