Holiday rentals with a patio in Sheffield

Cozy Lakefront Cottage w/Swim Spa & Firepit

Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

Glamping Getaway

Come enjoy the sounds of nature when you stay in this unique little getaway. Quaintly tucked away on beautifully manicured private property. Rest, relax & rejuvenate! Conveniently located near the Hudson River & Charles Rider boat launch 1/4 mile to enjoy fishing, kayaking or boating. Walking, hiking, biking trails & kayaking and restaurants located within minutes from the campsite. 5min drive to downtown Kingston, 10min to Historic uptown Kingston. 10min to Saugerties, Woodstock and Rhinebeck.

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

Lake Escape: Lake Cottage Charm, Lake Front, AC

Direct lakefront access with gorgeous views on a private lake. This beautiful 1930's lakefront cottage was fully renovated and reimagined by its owners in 2021. Custom architectural trim and details can be found throughout blending this homes' heritage with modern amenities. 2 bedrooms, eat-in kitchen and window seat nook, 2 full baths, custom barn doors and cabinetry, a reimagined sunroom, beautiful views on 100' of accessible lake frontage with outdoor patio, 1 mile from town center.

Stunning 1BR Apartment 1 Block from Warren

Outdoor space and a gorgeous huge apartment, completely private. One block from Warren, and steps from Hudson's newest and best: Return Brewing, Lil' Debs and Cafe Mutton. High ceilings, approximately 1500 s.f., gourmet kitchen with Blue Star Range, baby grand piano. Loaded with amenities, and most importantly, a huge garden and wrap around porch for your use with an outdoor eating and sitting space. Including a day bed porch swing for reading and naps. Come and enjoy Hudson!

Cozy Retreat at Branch Brook Campground

Welcome to your perfect getaway at Branch Brook Campground! Nestled amidst nature, our charming tiny cabin for two offers a cozy sleeping loft with a comfy futon, a well-equipped kitchenette, a welcoming living area. Outside, enjoy a private fire pit, cozy porch, and river views. The campground boasts scenic trails from Black Rock State Park and many amenities from Branch Brook - Including a Pool & Pickleball Court! Complimentary Wi-Fi and parking are provided. Book Now!

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. Ready to escape the ordinary? Book your stay today.