Vacation rentals with a fireplace in Woodstock

A peaceful stream runs beside a wooden structure, surrounded by lush greenery. Sunlight filters through the trees, creating a serene atmosphere. Smooth stones line the water's edge, enhancing the natural setting.

4.91 out of 5 average rating, 706 reviews

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

5 out of 5 average rating, 389 reviews

A rustic office area features warm wood paneling and a functional desk made of natural wood. A large flat-screen TV is mounted above a small electric fireplace. A comfortable black office chair is positioned at the desk, complemented by a chess set and decorative plant.

Guesthouse in Woodstock

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

A covered front porch is featured, showcasing black outdoor chairs positioned around a spacious area. A green planter overflowing with vibrant foliage adds a touch of nature, while sunlight filters through the trees, creating a serene atmosphere.

4.96 out of 5 average rating, 109 reviews

Romance+history+luxury+privacy in town=Maple House

Treat yourself to a romantic getaway or relaxing retreat in your own newly-renovated historic farmhouse, ideally located on a quiet dead-end lane just 1 block from the Woodstock Village Green ~ the heart of this famous “colony of the arts”. You can walk to restaurants, cafes, galleries, boutiques, theaters, clubs... Or you can stay home and relax in your private oasis of peace and beauty with a fully-fenced landscaped backyard, fireplace, chef’s kitchen, heated soaking tub, and luxury amenities.

4.98 out of 5 average rating, 535 reviews

A wooden sign is displayed on a brown wooden wall, reading 'THE BARN AT CRICKET RIDGE EST 2014'. The sign is crafted with a rustic design and is accompanied by a small piece of dried foliage. A stack of logs is located at the base of the wall.

Guesthouse in Bearsville

Relax on the Ridge - 2 miles from Woodstock

Stay and relax in a private guest house on a 5+ acre picturesque property overlooking historic Woodstock, N.Y. The cottage is nestled away high on a private road in a quiet country setting, yet conveniently only 2 miles from Woodstock and 10 miles from Phoenicia! Relax on the grounds while watching our Tennessee Mountain, Cashmere & Kiko goats—drive into town to enjoy shops, restaurants, & the unique artistic culture of Woodstock—explore the many beautiful trails that the Catskill Park offers.

4.98 out of 5 average rating, 118 reviews

The A-Frame cabin features a distinctive triangular structure framed by large windows. Surrounding greenery enhances its secluded appearance. A wooden deck and steps lead to the entrance, welcoming guests to the inviting outdoor space. Warm light peeks through, highlighting the cabin's charm.

Cabin in Saugerties

Sweet Saugerties A-Frame - 10 mins from Woodstock

This sweet A-Frame hideaway located in a wooded area between Saugerties and Woodstock will welcome you and warm your spirit with its charm. Featuring 2 bedrooms, each with Queen Beds, and a couch that folds out to a Full Bed, there's ample space for 4. But, it's also a serene escape for an individual or couple. An inspiring creative retreat, the home has beautiful views, and an electric piano. Quiet but 10 mins from great restaurants! 11 mins to HITS, 30 mins to skiing at Hunter Mountain.

Superhost

The exterior showcases a charming carriage house with distinctive blue shingle siding and pink door accents. Lush greenery borders the driveway, which leads to the entrance. A large tree provides shade, while an open sky with scattered clouds enhances the serene atmosphere.

Guest suite in Woodstock

4.83 out of 5 average rating, 506 reviews

The Carriage House: Garden Apartment

We offer a private studio apartment located on the first floor of this wonderfully restored 2 unit carriage house, built in the early roarin' 20's! It offers a blend of modern decor and amenities, with more traditional countryside accents. The design, using the original carriage doors in the architecture, allows light to pour through the apartment, while making adjustments for sleeping in easy. This truly unique space is a perfect place to take a weekend to relax, and even enjoy our grounds!

4.84 out of 5 average rating, 257 reviews

A charming town square is highlighted with lush trees and neatly arranged stone pathways. In the background, a tall church steeple is visible against a cloudy sky, while the American flag gently waves. Benches are placed invitingly throughout the area.

Cottage in Woodstock

Woodstock Dog friendly Cottage in Town; large yard

Charming Country Escape – Pet-Friendly & Walk to Village Green! Enjoy country charm and modern comforts in this newly updated 2-bed, 1.5-bath home. Just 2.5 blocks from the Village Green, it’s the perfect getaway for city folk with dogs. Relax in the private backyard with waterfall sounds or stroll to shops, restaurants, and trails. Features include a cozy woodstove, updated kitchen & bath, queen beds, and a master bedroom with an en-suite plus a balcony. You and your pet will love it here!

4.93 out of 5 average rating, 225 reviews

Home in Mount Tremper

Mt. Wonder: Cold Plunge, Sauna, Hot Tub and View

Welcome to the most splendid view in the Catskills. With a private outdoor spa. And just 10 min to Woodstock. This secluded cabin sits on 18 acres w/ private creek access & forest. Seeking a vacation w friends or a romantic escape? This is the place. Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub, sauna & cold plunge Amenities galore incl the spa, BBQ, firepit, games, wood stove & stocked kitchen. Peruse our books, be in nature or enjoy hikes & towns. This is the one.

4.94 out of 5 average rating, 301 reviews

A charming wooden cottage is nestled among tall trees, lightly covered in snow. The two-story structure features large windows and a spacious deck, with minimal outdoor furniture visible. The tranquil winter landscape is enhanced by softly falling snowflakes and a blanket of snow on the ground.

Cottage in Saugerties

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

4.96 out of 5 average rating, 351 reviews

A small stone guest house is framed by a snowy landscape. A prominent star decoration is mounted on the chimney, while bright blue windows contrast against the rustic stone exterior. A wooden deck is visible, providing an inviting outdoor space.

Guesthouse in Woodstock

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace

Snuggle by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical home has a private deck w/bbq, a garden with a hammock and fire pit. A full size Murphy bed with a full kitchen (except for an oven). You will have access to the entire guest house. A short drive to the beautiful, eclectic, funky town of Woodstock. Art & culture, restaurants, hiking & biking all nearby. Electric heat, ceiling fan, a standing ac unit and single person shower.

A spacious outdoor deck is surrounded by trees, inviting nature inside. A dining table with benches sits adjacent to the stylish mid-century chiminea, softly illuminated by string lights. Comfortable seating arrangements are positioned for relaxation, enhancing the outdoor entertainment space.