Cottage vacation rentals in The Berkshires

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Popular amenities for The Berkshires cottage rentals

Cottage rentals with a hot tub

Guest favorite
A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.
Cottage in Guilford
4.95 out of 5 average rating, 180 reviews

Luxury cottage by the sea with hot tub and pool

ElizabethRating, 5 stars1 month ago
Perfect spot for a quiet weekend getaway! We were able to go to Yale art museums for the day and then came back to check out the beaches. Definitely recommend the trip to Dockside Seafood and Grill in Branford for lobster pasta! The hot tub was also the best way to end the day with a peaceful beautiful view!! Would definitely go back again!
Top guest favorite
Cottage in Burlington
4.98 out of 5 average rating, 118 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

KimberlyRating, 5 stars2 weeks ago
I went here on a peaceful getaway with my partner for my birthday , and it was better than anything I could've imagined. exactly what we needed and even more beautiful in person than in the pictures! We had multiple questions for Feyza and she always answered very promptly. was such a clean spacious and peaceful getaway. couldn't have asked for more 😭
Guest favorite
A spacious living area features a cozy leather sectional sofa adorned with decorative pillows. A round coffee table sits in front, and a dining table for four is visible nearby. Natural light filters through the window blinds, complemented by warm overhead lighting.
Cottage in Saratoga Springs
4.97 out of 5 average rating, 117 reviews

The King's Cottage- HOT TUB and Pet Friendly!

JessicaRating, 5 stars1 day ago
We had a great time! Everything was thought of in this space. We especially enjoyed the opportunity to be outdoors and the proximity to the park. I'm not sure if this jumped out in the listing, but the place is walking distance to the Children's Museum which was perfect for us, as I had take the car for a work event and left my husband and 3 year old to explore the museum, and they could easily walk home to the cottage. Thanks for sharing your place with us!
Superhost
A vintage cottage is surrounded by vibrant autumn trees with red and yellow foliage. The ground is covered in fallen leaves, and a stone wall lines the edge of the property, providing a natural border. The sky features scattered clouds, enhancing the seasonal ambiance.
Cottage in Litchfield
4.86 out of 5 average rating, 345 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

ZacharyRating, 5 stars2 weeks ago
Took a getaway to Martin's cottage for a long weekend and could not have been happier. It was immaculately clean and the hot tub was ab amazing way to relax. I look forward to being back.
Top guest favorite
A hot tub sits on a wooden deck surrounded by lush trees, offering privacy and a natural setting. Nearby, a cozy seating area is arranged with black chairs and a small table, providing a space to relax and enjoy the tranquil environment.
Cottage in Kerhonkson
4.99 out of 5 average rating, 174 reviews

Ye Little Wood | Cozy Forest Cottage with Hot Tub

EmmaRating, 5 stars1 week ago
Danny and Travis are excellent hosts ! The house is gorgeous and extremely clean and well maintained. The kitchen is very well stocked with cooking utensils/ pots which is awesome for people who enjoy cooking (like we do). This is our second time staying here and we absolutely love it and plan to return.
Guest favorite
The spacious deck is softly illuminated by string lights, creating a serene atmosphere. A jacuzzi, elegantly positioned, offers a relaxing retreat, while surrounding trees provide a sense of seclusion as night falls.
Cottage in Monticello
4.91 out of 5 average rating, 119 reviews

Lovely Cottage w/ Jacuzzi+Woodstove!

AbbyRating, 5 stars1 month ago
Perfect, modern yet cozy cabin. The aesthetic was beautiful and was fully stocked with everything you could need. The neighbors are close but we never saw them. Maybe because we came up before the season picks up. We utilized all of Bilen's local recommendations. We loved the Local Table & Tap. Beautiful views. We also took a drive to Upward Brewing which was phenomenal. Keeping this Airbnb in my go-tos. Couldn't be happier :) Perfect for nature lovers.
Superhost
A wooden deck is furnished with comfortable seating and a coffee table, providing a serene view of rolling mountains and a tranquil pond. The sky is filled with fluffy clouds, reflecting warm hues as the sun sets, enhancing the natural beauty of the landscape.
Cottage in Denver
4.94 out of 5 average rating, 139 reviews

Country Cottage w/ HOT TUB & Views

ДианаRating, 5 stars1 week ago
Everything about our stay was perfect! The house was spotless, cozy, and located in a great area. The host went above and beyond — always in touch, helpful, and kind. We truly felt welcomed and taken care of. Would absolutely stay here again!
Guest favorite
The entrance of a cottage is framed by lush greenery, showcasing a welcoming wooden porch and a dark door. Potted plants add a touch of charm to the inviting pathway, which leads through a grassy yard.
Cottage in Boiceville
4.98 out of 5 average rating, 114 reviews

Hot Tub & Chic Catskills Woodstock Design Retreat

JordanRating, 5 stars4 months ago
We always stay at Little Willow when we go skiing at Belle Ayre. I think our three years and running relationship with the house tell you all you need to know about working with the Little and Littler gang and their spot.

Pet-friendly cottage rentals

Guest favorite
Cottage in Kingston
4.92 out of 5 average rating, 376 reviews

Kapitan’s Cottage: Private Retreat with Salt Pool

LydiaRating, 5 stars1 week ago
The house and property were absolutely lovely, clean, and peaceful. We had everything we needed. When there was a big rain storm and the internet had some issues, the hosts responded immediately and reset the modem and offered to call Spectrum. Issue was fixed right away. The pool was perfect temp and so restorative. Would 12/10 recommend staying here.
Guest favorite
A rustic cottage is surrounded by lush greenery, featuring a wrap-around deck illuminated by string lights. The wooden structure is complemented by various plants and shrubs, offering a serene and inviting atmosphere. The entry is adorned with a partially covered porch, enhancing the cottage's natural charm.
Cottage in Phoenicia
4.94 out of 5 average rating, 266 reviews

Charming creekside cottage in Phoenicia

YramisRating, 5 stars1 month ago
My stay was super nice, even with the rain. My fur baby and I had a great time. The cottage is very cozy and offers an immense sense of peace. My fur baby's favorite part was the backyard. We spent most of our time playing fetch. Chloe is super friendly. I will visit the cottage again.
Top guest favorite
A serene landscape is captured with bare trees standing against a colorful autumn sky. Vivid red and orange foliage is visible in the distance, set against fields of green, while a rustic stone wall lines the property. The tranquil scene invites a sense of peace.
Cottage in Sharon
4.93 out of 5 average rating, 181 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

JenniferRating, 5 stars4 days ago
This is our second time staying at Foxfire Hill, and it was wonderful to see the gardens in their glory. Great and responsive hosts. I’m sure we will be back again.
Top guest favorite
Cottage in Saugerties
4.97 out of 5 average rating, 126 reviews

Cottage on the creek with wonderful waterfall view

CynthiaRating, 5 stars6 days ago
R’s place restored our faith in beautiful and affordable air bnbs! We said numerous times during our stay that we would definitely be back. The setting was so beautiful and the outdoor spaces were incredibly enjoyable, especially with our dog. R’s kitchen is the best and super well stocked so we enjoyed many meals in. This place did not disappoint and we cannot wait to go back!
Superhost
A wooden deck extends from the cabin, featuring a round table with two transparent chairs. The view includes a forest of bare trees under a setting sun, casting warm light across the space.
Cottage in Rhinebeck
4.93 out of 5 average rating, 286 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

AnnaRating, 5 stars2 weeks ago
Nice surroundings, well equipped for a few meals, and comfortable sleeping for our family visiting the area.
Guest favorite
A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.
Cottage in Putnam Valley
4.89 out of 5 average rating, 271 reviews

Lakefront Cottage near Hudson Valley

BrianRating, 5 stars1 month ago
Stayed for a long weekend with my wife and two dogs. Cottage was comfortable and clean with an amazing view of the lake with a nice patio and access to the dock which we enjoyed. Also great location just a bit over an hour from the city but within a 15 minute drive to many great hikes and close to many great food options. Tony was also very responsive and helpful with recommendarions. Highly recommend.
Guest favorite
A golden retriever sits on a wooden dock at sunset, reflecting on the calm lake. The sky features varying hues of orange, blue, and pink, mirrored in the water's surface. Nearby trees and distant houses are softly illuminated by the fading light.
Cottage in Monroe
4.99 out of 5 average rating, 159 reviews

Cozy Lake Cabin

JenniferRating, 5 stars3 days ago
My husband and I stayed at Kevin’s place for a couple days in early June for a quick city getaway. Kevin was super responsive from the beginning all the way to check out and was a pleasure to communicate with! He is a fascinating well-travelled host with lots of cool souvenirs around the cabin from his travels and sports accomplishments. His place was very relaxing and was exactly what we were looking for with its lake front access and cosy interior. We travel for work and are constantly staying in nice hotels, and we had the most amazing sleeps in the memory foam bed with sheepskin duvet and agreed it was better than any hotel sleep we had recently. So peaceful! We canoed to a Mexican restaurant across the river for lunch which was a fun mini adventure and very delicious! When we checked out we got to meet Bodie, Kevins Golden Retriever that is in the listing photos. Was an awesome experience! We look forward to returning sometime back to Kevin’s Cabin!
Guest favorite
A spacious kitchen is equipped with white cabinetry and a large wooden island, featuring bar seating. Natural light floods the room through multiple windows. A dining table for six complements the space, with a fruit bowl as a centerpiece.
Cottage in Sheffield
4.94 out of 5 average rating, 154 reviews

Cheerful 3-bedroom cottage with woodstove.

AvivRating, 5 stars1 week ago
Just like the pictures , very peaceful and serene , the kitchen is well equipped. The beds are comfy. Great place to relax in the Berkshires. With a super responsive host.

Private cottage rentals

Guest favorite
The exterior of a two-and-a-half story salt box home is depicted under a night sky, featuring soft warm lighting emanating from the windows. Surrounding trees are silhouetted against the backdrop, while snow blankets the ground. A parked vehicle is visible beside the house.
Cottage in Newfane
4.9 out of 5 average rating, 255 reviews

Ridgeview: Cozy Cottage with a View

CalebRating, 5 stars1 month ago
We had a great stay over Easter weekend at James' cabin. It's on the small side but was perfect for the getaway my wife and I had planned. There is a 2nd bedroom that would have suited usl if we brought our kids or went with a 2nd couple, but we were glad for the extra room. I will add that the photos don't really do justice to the space. During the day, the cabin is particularly beautiful, the high ceiling filled with light and views of the surrounding forest and mountains. We saw owls, wild turkeys and an array of other birds. The site is very private - there are neighbors, but a good way off, though we enjoyed meeting them on our walks. James is a thoughtful, friendly and detail-oriented host, with a thorough guidebook full of great local recommendations. We know the area a bit and can say his suggestions are spot on (we particularly enjoyed our visit to the Fat Crow). I also recommend a stop at Duttons, and for easy views, a short drive to the top of Newfane Hill Road.
Top guest favorite
An open-plan living area features wooden beams and light-colored cabinetry. A modern kitchen with stainless steel appliances is visible beside a dining table. Natural light fills the space, highlighting a comfortable seating area adorned with a neutral-colored sofa and decorative rugs.
Cottage in Rhinebeck
4.99 out of 5 average rating, 152 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

ReneéRating, 5 stars3 weeks ago
It was perfect!! Just as described and we loved the whole place - the town is adorable too. Melissa was so helpful with great recommendations and we’ll definitely be back!
Guest favorite
A black barn-like structure is complemented by a spacious wrap-around deck. Several gray Adirondack chairs are arranged, facing the lush green lawn and surrounding trees. Expansive glass windows reflect the natural light, emphasizing the connection between indoor and outdoor spaces.
Cottage in Poughkeepsie
4.91 out of 5 average rating, 353 reviews

Be in Nature at this Gorgeous Riverfront Cabin

MJRating, 5 stars2 days ago
A lovely home with beautiful views of the surrounding woods from each room. Very clean, modern, and comfortable with a well stocked kitchen. Mark provided detailed and useful info on the place and the surrounding area. A great spot if you’re looking for some peace and quiet close to all the local attractions of the Hudson Valley.
Superhost
A charming yellow cottage is set amidst a natural landscape, featuring a welcoming front porch with steps leading to the entrance. Soft lighting from the interior creates an inviting glow, while a decorative white dog figure adds a touch of whimsy to the exterior.
Cottage in Highland
4.9 out of 5 average rating, 624 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

CaseyRating, 5 stars3 weeks ago
If you’re reading reviews to determine if you should book this bnb, BOOK IT! The cottage is tucked away in the corner of the property surrounded by lush trees, leaving you with a gorgeous view, but easy to find when walking up. You’re not far from small towns with shops and restaurants, breweries with mountain view’s, and many hiking spots. We are already planning our next trip!
Guest favorite
Cottage in Lanesville
4.95 out of 5 average rating, 186 reviews

Creekfront Cottage between Phoenicia & Hunter Mtn.

LisaRating, 5 stars7 months ago
We were expecting a peaceful, rustic, laid-back experience, and that's just what we got...and more. The cottage is situated in a lovely setting surrounded by trees, right at the edge of a picturesque brook. The inside was all we could ask for and more. So inviting and clean. Oozing warmth and charm. Every time we needed something, we could find it already supplied. The hosts clearly have thought of everything. We also loved the surrounding area. We spent lots of time in local eateries, checking out the nearby towns, and visiting the dozens of antique shops nearby. We had a wonderful time.
Top guest favorite
Cottage in Colchester
4.97 out of 5 average rating, 174 reviews

Lakefront peaceful getaway cottage

JamesRating, 5 stars3 weeks ago
What a wonderful and peaceful location! Doreen was very responsive and exceptionally helpful. The pictures are spot with a very clean and well stocked home. Amazing views from the bedroom and second floor deck. Amazing place to fish, kayak, and just enjoy the scenery! Enjoyed hiking nearby, great food in the area and a very scenic location to relax.
Guest favorite
A charming street scene captures vintage-style buildings, adorned with holiday wreaths and white lights. Soft snowfall creates a serene atmosphere, while a clock tower is visible in the background, contributing to the quaint character of the area.
Cottage in Goshen
4.94 out of 5 average rating, 124 reviews

Country Cottage in Goshen

VioletteRating, 5 stars3 months ago
Such a sweet cottage with great decor and beautiful kitchen + nice quiet outdoor area. Lovely to go to with your mate. We felt right at home here!
Guest favorite
A serene winter scene features a gently flowing stream bordered by freshly fallen snow. Shadows from trees gracefully stretch across the snow-covered landscape, creating a tranquil atmosphere. The ice along the banks contrasts with the dark water, enhancing the natural beauty of the winter setting.
Cottage in Copake Falls
4.91 out of 5 average rating, 356 reviews

Beautiful cottage at the foot of the Birkshires

VivianRating, 5 stars2 weeks ago
Our extended family goes tent-camping in nearby Taconic State Park. We enjoy the campsite during the day but repair to this sweet, charming house nearby to sleep. It’s clean and comfy and within one minute of the campsite. This house let us enjoy the best of both worlds. Thank you for a lovely weekend.

Destinations to explore