Holiday home rentals in The Berkshires

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.

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

*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, you'll be in proximity to the best of the Catskills: skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Amenities includes business Wifi, gourmet kitchen, washer/dryer, deck w/ bbq grill, outdoor fire pit, badminton, and more.

Lakefront A-Frame in the ADKs with Watersports

Enjoy the peacefulness of nature when you stay in this clean, modern A-frame that sleeps up to 6. Pet friendly and remodeled for the perfect romantic getaway or fun for the whole family! Offering 120 ft of safe lakefront access and views, one indoor and two outdoor fire pits and plenty of Adirondacks chairs for everyone. This A frame offers high speed Wi-Fi and streaming. 15 minutes from restaurants, Golf Course, Skiing, snowmobiling, hiking and biking trails, music festivals in summer.

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.

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.

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!

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Come as you are - we welcome ALL visitors. Relax and soak in your surroundings in this new 1 bedroom vacation spot. Part of a barn conversion, the space is clean and bright and ideally located for those exploring all the Berkshires has to offer. Perfect for an individual or couple looking to escape to a serene and beautiful setting - a stream abuts the property and hiking/snowshoeing trails are accessible out the front door.

Private, modern carriage house. Great for couples.

Newly built in 2022, our charming, modern carriage house is tucked away within a small courtyard garden on a quiet residential street in the heart of Beacon NY. Guests will enjoy an efficient, elegantly designed and furnished interior with views of the Mount Beacon ridgeline from this comfy and private abode. The owners are long-time Airbnb hosts who work hard to ensure their guests have a peaceful, relaxing stay.