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Cabin vacation rentals in Chatham

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Quick stats about cabin rentals in Chatham

  • Nightly prices starting at

    Chatham vacation rentals start at €331 per night before taxes and fees

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chatham rentals

  • 5 Average rating

    Chatham stays are highly rated by guests—averaging 5 out of 5!

Top-rated cabin rentals in Chatham

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

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Top guest favorite
Cabin in Chatham

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

4.92 out of 5 average rating, 147 reviews
Top guest favorite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

4.99 out of 5 average rating, 159 reviews
Top guest favorite
The kitchen features deep black cabinetry paired with warm wood countertops. A window above the sink allows natural light to illuminate the floral wallpaper. Modern fixtures and a stylish faucet enhance the space, offering a functional area for meal preparation.
Cabin in Hudson

Cozy Grove Luxury Cabin

Luxurious, lovingly-appointed mid-century country retreat located less than 15 minutes from restaurants, galleries, and shopping in downtown Hudson, nestled between farmers’ markets, breweries, cideries, distilleries, hiking, and more! Recently-renovated 1958 cabin features a deep soaking tub, outdoor hot tub, woodstove, and upscale amenities. Set back from the road amidst a grove of pine and apple trees, it's the perfect spot for kicking back in luxury after a day exploring local attractions.

4.96 out of 5 average rating, 126 reviews
Top guest favorite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

4.97 out of 5 average rating, 109 reviews
Top guest favorite
Cabin in Catskill

Away from all - Modern Cabin in the woods

Escape to serenity in our cozy cabin nestled in the heart of the woods! Surrounded by towering trees & the soothing sounds of nature, this secluded retreat offers the perfect blend of peace & adventure. Inside you'll find a warm & inviting atmosphere, complete with rustic charm & modern design. Explore our private trail that takes you to a beautiful creek, or relax in the tranquility of the forest by the fire. The perfect getaway for travelers seeking a digital detox & a connection with nature

4.99 out of 5 average rating, 100 reviews
Top guest favorite
A modern A-frame cabin is illuminated under the evening sky, featuring large glass doors that open to a spacious deck with outdoor seating. The surrounding wooded area is visible, adding to the tranquil setting of the nature retreat.
Cabin in Freehold

Tiny Home A-Frame with Hot Tub & Creek

Just a little over 2 hours from NYC, the Cozy A-Frame is a 400 sq foot, eco-friendly, creekside cabin set in the Northern Catskills of New York. Our getaway has been thoughtfully designed to include many indulging comforts while secluded in nature. Take in the calm of the woods from the hot tub or while roasting s'mores at the fire pit. Or turn up the music on the vintage stereo and watch the snow fall. An ideal getaway for those seeking a romantic escape or a change of pace to work in nature.

4.95 out of 5 average rating, 359 reviews
Top guest favorite
A bright and inviting living area features large windows that offer views of the surrounding greenery. A comfortable sofa and chairs surround a coffee table, while a desk with a chair is positioned near the window for a productive workspace.
Cabin in Ghent

Cozy chalet w/ deck, fireplace, by Hudson & hiking

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

4.99 out of 5 average rating, 350 reviews
Guest favorite
A spacious deck features two wooden lounge chairs and a small side table, surrounded by lush greenery. The railing provides unobstructed views of the wooded area, allowing natural light to create a serene atmosphere.
Cabin in Town of Hillsdale

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

4.91 out of 5 average rating, 129 reviews
Guest favorite
The lodge features a rustic wooden exterior, set against a backdrop of lush greenery. A shaded porch is visible, with seating and soft landscaping that includes flowering plants and shrubs. A stone chimney rises from the side of the cabin, blending harmoniously with the natural surroundings.
Cabin in West Sand Lake

The Lodge at June Farms

See more of us on Prime Video's tv show, June Farms... streaming now! This cabin is a stunning, rustic, open-floor-plan retreat. The screened-in front porch looks down onto our horse pasture. This cabin is our most romantic cabin on the property. Our gigantic rain shower in the bathroom has an 8'x5' wall mirror and a French door that opens out to the forest. If you are a cook, this cabin is a chef's dream. You might also like our stunning new cabin called The Farmhouse.

4.96 out of 5 average rating, 354 reviews
Top guest favorite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top

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. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

4.99 out of 5 average rating, 184 reviews
Top guest favorite
An aerial view captures the serene expanse of the Hudson River, with gently rolling hills and trees framing the water's edge. The property is positioned near the shore, showcasing a mix of gravel and grassy areas leading to the river, inviting a sense of tranquility.
Cabin in Catskill

Riverside Retreat on the Hudson - Modern Cottage

Welcome to the Riverside Retreat on the Hudson, a modern renovated cottage located directly on the Hudson River! Enjoy the beautiful panoramic views from the comfort of the house or in the Adirondack chairs on the patio. Secluded and serene, yet minutes away from downtown Catskill (5 minutes) and Hudson (15 minutes). Hunter and Windham are 30 minutes away for hiking and skiing! We are so excited to share this very special place with you!

4.99 out of 5 average rating, 201 reviews
Top guest favorite
A spacious living area features a large green sectional sofa, complemented by decorative cushions. A flat-screen TV is mounted above a stone fireplace. Large windows provide natural light and views of the surrounding forest, while a coffee table is positioned in front of the seating arrangement.
Cabin in Cairo

The Catskill Equestrian Cabin

Decompress in this beautiful, calm, serene new cabin build nestled in the mountains on a peaceful, private five acre lot, bordering an equestrian center. Walk less than two minutes to see the horses during your stay. The cabin is less than 15 minutes to Windham mountain for winter skiing and under 20 minutes to the popular town of Catskill. This cabin has all the amenities you need for a wonderful stay. We hope to host you soon!

5.0 out of 5 average rating, 105 reviews

Popular amenities for Chatham cabin rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cabin rentals with a hot tub

Guest favorite
An open living area features high ceilings with exposed wooden beams. A comfortable gray sofa and a round coffee table sit on a traditional rug. A kitchen island with bar seating is visible, along with a modern television mounted on the wall.
Cabin in Catskill

Modern cabin retreat

4.96 out of 5 average rating, 198 reviews
Top guest favorite
An open concept kitchen and living area showcases wood beam ceilings and shiplap walls. The kitchen features vintage cabinetry, a central island, and a gas stove in deep blue. Cozy seating options are arranged around a decorative rug, with natural light filtering through a window adorned with bamboo shades.
Cabin in Coxsackie

Cozy French country cottage by creek w/hot tub

4.98 out of 5 average rating, 100 reviews
Top guest favorite
Cabin in Prattsville

Romantic Catskill Getaway | HotTub w/Mountain View

4.99 out of 5 average rating, 299 reviews
Superhost
A cabin nestled among tall trees is gently illuminated at dusk. Soft light streams through the open sliding door, revealing a cozy sleeping area with a person resting on a bed. The surrounding forest is lush with greenery, enhancing the serene atmosphere.
Cabin in Saugerties

40-Foot Container Cabin in the Catskills

4.85 out of 5 average rating, 361 reviews
Superhost
The kitchen features green cabinetry with a white countertop. Shelves above hold various jars and glasses. A window allows natural light to brighten the space, with a view of nature visible outside. Additional storage includes a fridge and a stainless steel trash bin.
Cabin in Athens

Charming Lakefront Cabin with Hot Tub

4.93 out of 5 average rating, 141 reviews
Top guest favorite
A spacious deck features a charcoal grill and a table set for dining under a large umbrella. Surrounding trees provide a green backdrop, while views of distant mountains can be seen in the background. A lounge chair adds to the outdoor relaxation space.
Cabin in Catskill

Catskills Log Home, Stunning Mountain Views

4.96 out of 5 average rating, 292 reviews
Top guest favorite
The cabin's exterior is framed by lush greenery, featuring large windows that invite natural light. A deck extends from the side, offering a seamless connection to the surrounding woods. The dark wooden siding complements the serene outdoor environment.
Cabin in Red Hook

Secluded Cabin in Woods With Hot Tub

4.94 out of 5 average rating, 111 reviews
Guest favorite
A screened-in area features a hot tub, inviting relaxation while offering views of the surrounding woods. A wall-mounted TV provides entertainment options. One clear chair and a small side table are positioned nearby, enhancing the cozy atmosphere of the space.
Cabin in Catskill

Catskills Loft Cabin w/ Hot Tub

4.95 out of 5 average rating, 182 reviews

Pet-friendly cabin rentals

Guest favorite
Cabin in Athens

Cool Cozy Cabin by the Lake

4.96 out of 5 average rating, 136 reviews
Top guest favorite
Cabin in East Nassau

Berkshire’s Blue Cabin

4.98 out of 5 average rating, 188 reviews
Guest favorite
The A-frame cabin is surrounded by lush greenery, featuring a sloped black exterior and large windows. A wooden deck is visible, equipped with two Adirondack chairs. Soft landscape lighting enhances the entrance, while the tranquil wooded setting provides a serene atmosphere.
Cabin in Kerhonkson

Black A-Frame: Catskills Cabin

4.95 out of 5 average rating, 122 reviews
Guest favorite
An open-plan kitchen and dining area features a modern design with green cabinetry and natural wood accents. A wooden dining table is surrounded by four chairs, and large windows allow natural light to fill the space. A ladder leads to a loft area.
Cabin in Catskill

A-Frame w/ Big Yard | 15 min to Hudson, NY

4.91 out of 5 average rating, 263 reviews
Top guest favorite
An inviting living space features a modern wood stove as its focal point. Large windows allow natural light to fill the room, revealing views of the surrounding trees. Two comfortable sofas are arranged for relaxation, with a hanging planter adding a touch of greenery.
Cabin in Town of Ancram

The Ancram A - Luxury Mid-Century Modern Cabin

5.0 out of 5 average rating, 164 reviews
Top guest favorite
A modern cabin is nestled among lush greenery, showcasing a covered porch that extends from its large glass windows. A neatly manicured lawn, bordered by wood chip landscaping, leads to the wooden steps of the porch, emphasizing the tranquility of the natural surroundings.
Cabin in Saugerties

Cozy Catskills Cabin

4.98 out of 5 average rating, 193 reviews
Top guest favorite
Cabin in Cornwallville

The Log Cabin in the Catskills

4.97 out of 5 average rating, 600 reviews
Guest favorite
A gentle waterfall cascades over rocky terrain, surrounded by autumn foliage in varying shades. The water flows into a clear pool, with smooth stones lining the edges. Tall trees in the background create a lush, green canopy, while fallen leaves blanket the ground.
Cabin in Rhinebeck

Sunset Bungalow-Mt views on 130acre forest & falls

4.88 out of 5 average rating, 461 reviews

Private cabin rentals

Superhost
Cabin in Stephentown

Rustic Cabin | Barrel Sauna | Private Pond

4.86 out of 5 average rating, 315 reviews
Superhost
A rustic cabin is nestled among tall trees beside a flowing stream. The deck extends over the water, while natural stones and moss line the streambed. Fallen leaves cover the forest floor, creating a serene woodland atmosphere.
Cabin in Monterey

Secluded cabin with babbling brook

4.87 out of 5 average rating, 259 reviews
Top guest favorite
The cabin’s exterior is surrounded by trees, featuring a sloped roof and large glass doors that invite natural light. A spacious deck is furnished with multiple red tables and chairs, ideal for outdoor dining. A grill is positioned nearby, with a gravel pathway leading to the surroundings.
Cabin in Petersburg

Cozy Retreat in the Trees

4.94 out of 5 average rating, 283 reviews
Top guest favorite
A wooden porch with two rustic chairs provides a view of the expansive landscape. The sunset casts warm colors across the sky, while the horizon stretches over a wooded valley. Logs are stacked along the edge, enhancing the serene atmosphere of the setting.
Cabin in Palenville

Big Medicine Ranch-Rustic Sunrise Cabin-Catskills

5.0 out of 5 average rating, 314 reviews
Top guest favorite
Cabin in Woodstock

Byrdcliffe Artist Studio (27.1-1-70)

4.93 out of 5 average rating, 887 reviews
Top guest favorite
The A-frame exterior features a steeply pitched roof and wooden siding, surrounded by tall trees. A stone pathway leads to the entrance, which is framed by two potted plants. Decorative stained glass adds a unique touch to the central door.
Cabin in Cairo

Cozy Catskill A-Frame on 4-Acres

4.94 out of 5 average rating, 207 reviews
Top guest favorite
A charming cabin stands surrounded by trees, illuminated by soft string lights. A fire pit with glowing embers is positioned in front, with a charcoal grill nearby. The cabin features large windows, allowing for views of the serene wooded landscape.
Cabin in Kerhonkson

Cozy Cabin | Fire pit + Hiking + Pets Welcome

4.96 out of 5 average rating, 655 reviews
Guest favorite
Cabin in Colebrook

Rustic Pond Cabin: Nature, Stars & Serenity

4.95 out of 5 average rating, 130 reviews

Destinations to explore