Vacation home accommodations in Berkshires

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Top-rated vacation houses in Berkshires

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

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Superhost
The exterior of a three-story townhouse showcases a welcoming porch with a railing and multiple seating areas. Beautiful greenery surrounds the property, accentuating the wooden structure. A staircase leads to the upper level, while two planters with greenery add a touch of nature to the entrance.
Vacation home in Hudson
4.91 out of 5 average rating, 53 reviews

La Maison Hudson: Charming 1BR In Prime Location

Welcome to La Maison in Hudson! This charming three-story townhouse, just two blocks from vibrant Warren Street, is perfect for families, friends, or a romantic getaway. Apartment 2 offers 1 bedroom, 1 bath, and accommodates 2 guests. Enjoy cozy thrifted decor, a private balcony, convenient parking, and a fully equipped kitchen with a dining table for six. Warren St: 3-min walk Train station: 15-min walk Olana: 8-min drive Art OMI: 15-min drive Your ideal mix of convenience & culture awaits!

Superhost
An aerial view captures the lakefront vacation house surrounded by greenery and calm waters. The property features a spacious lawn leading to the lake, with several vehicles parked near the house, highlighting its accessibility and serene location in the lake community.
Vacation home in Athens
4.88 out of 5 average rating, 113 reviews

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Welcome to the newly renovated lakefront vacation house in the Catskills. It is perfect for family & friends looking for a getaway in the Hudson valley and Catskill mountains. Close to ski resorts like Hunter & Windham. This peaceful retreat is located in a beautiful lake community with a large waterfront backyard.  You will enjoy:  • Gathering around the fire pit by the waterfront with s’mores • Relaxing in the Hot Tub overlooking the lake • Wake up to the beautiful lake view from your bedroom

Guest favourite
The living room features a large sectional sofa with a plush texture, complemented by a soft area rug. Two mirrors and a modern light fixture add style to the neutral walls, while sheer curtains allow natural light to filter gently into the space.
Vacation home in Albany
4.92 out of 5 average rating, 172 reviews

Spacious Urban APT w/4BR & Office in Albany

Visiting Albany for work, vacation, or to visit family? The Twitchell Estate is a spacious 4BR home that will be perfect for your stay. This elegantly designed Boho Chic rental comes with amenities such as self-check-in, Netflix, Disney+, Apple TV, and many other streaming options if you're looking to relax indoors, and a private laptop-friendly office with Wi-Fi if you need to get work done. Enjoy free coffee and tea in the stocked kitchen, with everything you need to feel like you are at home.

Top guest favourite
Two comfortable chairs with soft cushions are positioned on a wooden deck, facing the tranquil waters of the Hudson River. A small, round table sits between them, holding two glasses. The scene captures a soft sunset glow reflected on the water, framed by distant hills.
Vacation home in Wappingers Falls
4.97 out of 5 average rating, 61 reviews

Once in a Lifetime Hudson River Views

Perfect for reunions, retreats, and celebrations. We designed Riverhouse so you can relax, recover, and get inspired. Gather in one of many common areas or chill in your own room with a view. Watch birds fly, fish jump and trains and ships go by. Chill in the hot tub, build a fire (and finally hang with your teenager), fly a kite , catch fish off a private dock. Morning coffee or sunset cocktails on the deck. Play pool, pingpong, or piano into the night. Drum circle and a dance party? YES!

Top guest favourite
An elegantly set dining table displays black plates, clear glassware, and cloth napkins. A lit candle adds a soft glow, while a modern kitchen is visible in the background, featuring stainless steel appliances and a cozy living area with seating.
Vacation home in Warren
4.98 out of 5 average rating, 196 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Top guest favourite
Vacation home in Pine Hill
4.99 out of 5 average rating, 149 reviews

The Perfect Catskills Escape for Families and Groups

Pine Hill House is a renovated 1870s boarding house with loads of old charm mixed in with new luxuries. Take a left from the house to find miles of hiking trails. Take a right and walk to town with its vibrant restaurant scene and a lively community center. Belleayre Beach and Belleayre ski area are both a 5-minute drive away, as are some of the Catskills' hottest restaurants, spas, and cider houses. Don't want to leave? Relax around the woodburning stove and soak in the clawfoot tub.

Top guest favourite
A modern kitchen is highlighted by a large island with a quartz countertop and seating. Natural light fills the space through broad windows, offering views of the surrounding greenery. Professional-grade appliances are provided, creating an inviting area for culinary activities.
Vacation home in Windham
4.93 out of 5 average rating, 107 reviews

*Farmhouse Chic with Mountain and Lake Views*

Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

Top guest favourite
A sleek, modern outdoor area features a table lightly dusted with snow, surrounded by illuminated string lights. The glass walls provide views of a snow-covered landscape with trees and a flowing river, creating a serene winter atmosphere.
Vacation home in Shandaken
4.97 out of 5 average rating, 216 reviews

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Rough cut beams, All new HVAC and Hearthstone soapstone wood burning stove. Take it easy at this tranquil getaway while you see and hear only the water flow with wrap around 4 season river right off deck. Close to scenic hiking, skiing, river tubing, and great restaurants along "Rapid Water"- The Algonquin Nation word for "Shandaken". Dogs welcome (Up to 2), sorry no cats.

Guest favourite
An open, airy space features a wooden staircase leading to the upper level. A small dining area includes a table and two stools, while a comfortable seating area is visible in the background. Natural light filters through large windows, illuminating the modern design.
Vacation home in Great Barrington
4.94 out of 5 average rating, 254 reviews

Home in Great Barrington. Steps from downtown!

First Things First… Let’s Keep the Love Alive! ❤️ 🙌 Central and Private! Just steps away from historic downtown Great Barrington. East Mountain Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶

Guest favourite
An aerial view reveals the property’s spacious layout, featuring a large home with a welcoming deck and outdoor seating. Surrounding greenery enhances the setting. Nearby structures are visible, showcasing varied architectural styles. The well-maintained grounds include steps leading down to the water's edge.
Vacation home in Southwick
5 out of 5 average rating, 6 reviews

The Lake

Welcome to Lake Congamond's North Pond! Wake up every day just steps from the water. Grill out on the brand new Trex deck with stunning water views, and dock your boats for the duration of your stay. This home features ample parking, central air, cornhole boards, an outdoor dartboard, and a propane-fueled fire pit. The location is great as the house is just minutes away from Bars, Restaurants, and Golf Courses. This vacation rental truly has it all! Book your stay today!

Guest favourite
The image captures a serene lakefront view, showcasing lush greenery surrounding a secluded house. A wooden dock extends into the calm water, providing access to the lake, while the sunlit landscape emphasizes the tranquility of the natural setting.
Vacation home in Becket
4.97 out of 5 average rating, 60 reviews

Perfect Serene Waterfront All Season Retreat!

Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two wooded acres of forested land. Explore the stream that runs through the property, or just sit on the large deck or down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. The sunny house has 2 bedrooms, study with sofa bed, 2 full baths, full kitchen!

Guest favourite
An open kitchen and dining area feature natural wood floors and high ceilings. The kitchen is equipped with modern appliances and a large island. Windows allow ample natural light, illuminating the dining table and additional seating areas. Exposed wooden beams add a rustic touch.
Vacation home in Salt Point
4.93 out of 5 average rating, 82 reviews

Riverfront rustic farmhouse near Rhinebeck

This historic Clinton Hollow house was built by Isaac Fraleigh in the late 1700's and overlooks the waterfalls of Wappingers Creek. The house has the architectural details of an antique colonial and the open, spacious feel of a modern contemporary. The great room with its big fireplace has different vibes and seating areas and is just perfect for family and friends gathering. The Petanque field in the garden add a fun convivial activity.

Popular amenities for Berkshires vacation houses