Cottage vacation rentals in The Berkshires

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Top-rated cottage rentals in The Berkshires

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Guest favorite

A stone path winds through a lush, green yard, bordered by trees and wooden fence posts. The inviting entrance of the cottage is visible, surrounded by vibrant flora, creating a serene outdoor setting that emphasizes the property’s natural beauty.

Cottage in Craryville

4.91 out of 5 average rating, 524 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit and laundry facilities. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking

Superhost

A wooden chair faces a gently flowing stream, surrounded by tall trees in a tranquil setting. Sunlight filters through the branches, creating a serene ambiance by the water's edge.

Cottage in Hobart

4.81 out of 5 average rating, 186 reviews

🌟Riverfront Cottage W/2 Bedrooms Catskills 🌟

Enjoy our renovated farm house. Relax at this peaceful riverside cottage. Listen to the passing stream from every room in the house. Cottage features a Hammock, backyard fire pit, private swimming hole, Trout fishing, voice activated speakers throug, full kitchen, two bedrooms with queen's and laundry.Surrounded by 200 acres of state land you're free to explore. Cottage is located in Hobart NY, the bookstore capitol of NY. 25 min to Plattekill Mountain ski resort, Belleayre Mountain Ski Center.

Top guest favorite

A charming studio cottage is nestled among trees, with a covered porch adorned by an American flag. Steps lead up to the entrance, and a wooden railing provides safety. Seasonal foliage in warm colors surrounds the area, complementing the rustic setting.

Cottage in Cortlandt

4.99 out of 5 average rating, 188 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Top guest favorite

A peaceful waterfall cascades over rocks, surrounded by lush greenery and trees. In the background, a quaint cottage is visible beside the tranquil pond, enhancing the natural beauty of the setting. Sunlight filters through the leaves, creating a serene atmosphere.

Cottage in Warwick

5 out of 5 average rating, 213 reviews

Cottage at Millpond Falls - Romantic Luxury Escape

Looking for a romantic getaway? Relax in this cozy cottage overlooking a waterfall in a private setting. We offer a 5-star premium experience! Super-clean and luxurious. One hour from NYC. Our most frequent review: "We can't wait to come back!" Nearby wineries, craft breweries. Minutes from Warwick village, restaurants, bars, antiques, shopping, Appalachian Trail, and Greenwood Lake. Apple picking, skiing and water park nearby. Close to LegoLand and Jehovah's Witness Headquarters.

Superhost

A cozy living area features a stone fireplace framed by vintage skis. Natural light streams through two windows, illuminating a plush sofa and an armchair. A glass coffee table rests on a colorful area rug, complemented by greenery in a pot and minimalist artwork on the walls.

Cottage in Gardiner

4.9 out of 5 average rating, 161 reviews

Little Cottage Under the Ridge

Visit the cottage for an upscale retreat in the rock climbing epicenter of New York’s famous Shawangunk ridge. our mountain top paradise sits on a dead end road amongst untouched nature, only minutes to town, with a small chef’s kitchen, breakfast bar, and brand new everything. As the last property before Minnewaska’s protected preserve land, the cottage offers unmatched peace and quiet. Enjoy a private campfire beneath mature maple & oak trees that decorate our secluded five acre property.

Guest favorite

A contemporary open-concept kitchen and living area features large windows that frame scenic views. A central dining table complements the kitchen with dark cabinetry and modern appliances. A comfortable couch with decorative pillows enhances the inviting space, while a vibrant potted plant adds natural greenery.

Cottage in Greenwood Lake

4.98 out of 5 average rating, 336 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #33593

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, 123 reviews

Country Cottage in Goshen

Quaint country cottage, with beautiful hardwood floors, screened in porch, claw foot bathtub and lots of antiques set on a naturally landscaped 1 acre property. The original cottage was built in 1932, but was completely renovated in the last 5 years. 650 square feet with a bedroom, bathroom, lounge on the 2nd floor loft, and an open floor plan with living area, dining area and kitchen on the first floor. French doors lead from the dining area to a large screened in porch.

Guest favorite

A wooden playground structure is set on a grassy area, featuring two green slides and swings. The structure showcases an alpine roof and windows, surrounded by open fields and trees under a partly cloudy sky.

Cottage in Goshen

4.92 out of 5 average rating, 307 reviews

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.

Guest favorite

A well-maintained cottage is framed by lush green grass and tall trees. A neat path leads to the front door, which is accented by a vibrant red door. The cottage overlooks a serene lake, enhancing its inviting exterior.

Cottage in Walden

4.96 out of 5 average rating, 108 reviews

Cute, Cozy, Lakefront cottage

Cute, cozy lakefront cottage on private lake. Deck with an unobstructed view of the lake. Stunning sunrises, pinewood floors in bedroom/living room/kitchen. Queen size bed in bedroom. Situated on the same lot as owner occupied main house. Quiet, residential area. Near wineries, breweries, hiking. WIFI. No TV. Unfortunately, due to severe pet allergies I am unable to host any kind of animals including emotional support and service dogs and cats of any kind.

Guest favorite

A bedroom features a spacious bed adorned with soft linens, positioned beneath large, angled windows that frame views of the surrounding greenery. A stone wall adds texture, while the ceiling fan promotes air circulation. Soft lighting from bedside lamps enhances the ambiance.

Cottage in Pawling

4.98 out of 5 average rating, 119 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Guest favorite

A snowy pathway leads from the cottage, flanked by trees on either side. Gentle, warm light from hanging bulbs illuminates the covered deck area, while a tranquil creek is visible in the background, with a soft blanket of snow covering the ground.

Cottage in Phoenicia

4.94 out of 5 average rating, 261 reviews

Charming creekside cottage in Phoenicia

Come relax in one of the prettiest places in the Catskills. Enjoy views of the Stony Clove, while sipping coffee on the wrap-around deck. The location is private and quiet, yet convenient to all the region's many attractions - hiking, skiing, antiquing, eating. When you are done exploring, enjoy a dip in one of the largest, deepest swimming holes in the area. Perfect for small families and couples. License Number: 2022-STR-AO-081

Superhost

A small outdoor seating area features two metal chairs and a round table, surrounded by lush greenery. The view looks out onto a calm lake, partially obscured by foliage, creating a serene and private atmosphere.

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you.

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What guests are saying

Cozy home in the Village of Greenwood Lake

4.93 out of 5 average rating, 181 reviews4 days ago

Would highly recommend staying here. Will re-book if we return to Lego-Land or surrounding area. Loved that there was everything you need for a home that you don’t bring/pack (hair dryer, silverware, plates, cleaning supplies, spices etc). Quiet area with nice neighbors and really good food places (1-3 min walk away).

Cottage in Greenwood Lake

What guests are saying

Berkshires Cottage by Lake. Year Round Adventures.

4.95 out of 5 average rating, 273 reviews2 months ago

loved this cozy cabin for a snowed in weekend. the setting is beautiful and the house is completely stocked with everything you could need for quiet time with family. we came with two small kids and it was well suited for them. hoping to come back in the summer to enjoy the lake. thanks Scott for being such a phenomenal and responsive host amid the crazy snow storm.

Cottage in Becket

What guests are saying

The Little House

4.98 out of 5 average rating, 565 reviews3 days ago

“The little house” is a wonderful place to stay! It’s super spacious and was everything we were looking for. A quiet getaway from all the hustle and bustle. Beautiful decor and I loved the fireplace! The beds were very comfortable. There were 4 of us and we all felt at home in Glenn’s place. Will definitely put it on my favorites list and will return for future trips to the Catskills.

Cottage in Roxbury

What guests are saying

Lakefront Lovely Cottage

4.83 out of 5 average rating, 47 reviews4 months ago

Brenda place was beautiful with a beautiful view especially when we work up to some light snow on the lake. The layout of the house was ideal for us with the big open living room and great updated kitchen. So many comfortable beds for us to use. Our favorite places were the sun room and dining rooms looking out at the lake, Brenda was was kind and helpful and adding a Christmas tree for us was a beautiful touch . Highly recommend, one of our best for sure, thank you

Cottage in Enfield

What guests are saying

The Cottage on Babbling Brook

4.95 out of 5 average rating, 196 reviews1 week ago

Super peaceful and tranquil! We were in town for the Gilmore Girls convention and absolutely loved our stay! Gorgeous surroundings and no noise even though you are right off the road. The creek outside was just beautiful and all the wood touches on the inside gave it that perfect "log cabin" feel. It was super clean and had all the amenities you could need. The wood burning stove was the cherry on top, making late night Netflix binges out of this world.

Cottage in New Milford

What guests are saying

The River Road Cottage

4.77 out of 5 average rating, 111 reviews6 months ago

Came up for a weekend away from NYC with my husband and another couple and our two dogs. House was great and in a great location - 10 mins away from downtown New Paltz. Went to Twin Orchards on the weekend which we highly recommend. There is A LOT to do in the surrounding area!

Cottage in New Paltz

What guests are saying

Serenity Cottage: Ski, Hike, Unwind & Explore

4.83 out of 5 average rating, 6 reviews2 months ago

Fouz and Chris's cottage was very nicely done, attention to detail where it mattered, such as the classic style appliances. We arrived and a bottle of wine was ready with glassware ready to go. The cottage was very well stocked with everything you need and organized. Just arrived and relax. When traveling there next, will definitely stay again.

Cottage in Shandaken

What guests are saying

Sunapee area lakeside cottages trio on Sand Pond

4.89 out of 5 average rating, 100 reviews8 months ago

We have been going to Sandpond every year for as long as I can remember. We love the lake and the area. Claudia's cabins provide us the ability to join our family there and have our own space. We absolutely love it and are already looking forward to next year!!

Cottage in Marlow

What guests are saying

Beautiful stream side cottage in the woods

4.87 out of 5 average rating, 222 reviews5 days ago

Beautiful secluded home - perfect for a few days of being off grid. Rose gave extremely clear instructions on how to find her place and was super helpful with questions and checking in. Home is wonderfully decorated and equipped. Would love to come back!

Cottage in Kerhonkson

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