Pet-friendly holiday rentals in Woodstock

The exterior of the cottage is shown, featuring rich wood paneling and large glass doors. A stone pathway leads to a charming seating area, which includes a decorative bench. Lush greenery surrounds the property, enhancing the natural environment.

4.91 out of 5 average rating, 750 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, 374 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, 108 reviews

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!

The cabin is set among lush greenery, featuring a dark exterior and a covered entryway. A well-maintained path leads to the entrance, with a manicured lawn displaying varied shrubbery and stones. Visible above is a satellite dish, indicating modern amenities in a natural environment.

4.9 out of 5 average rating, 623 reviews

The Pike Lane Cabin & Nature Preserve

The Pike Lane Cabin is nestled in the woods on 7 acres but walking distance to the center of Woodstock. This private retreat offers 2 sleeping areas. The oversized master has a queen bed and its own living area with a queen size sofa bed. The other sleeping area is a full pullout sleeper in the main room. Fully equiped kitchen, full bath, linens, TV, wifi, AC. Four adults allowed plus children 12 or under. Arriving in town early? Come enjoy the grounds or lay in a hammock while you wait until 3.

5 out of 5 average rating, 433 reviews

A spacious master suite features a wooden accent wall and vaulted ceiling. A large bed with decorative pillows is positioned centrally, flanked by nightstands. In the background, a private bathroom is visible with modern fixtures and a wooden sink. Natural light filters through nearby windows.

Guesthouse in Woodstock

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

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "PREMIER" 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

The cabin's exterior is characterized by natural wood siding and large glass panels that integrate the structure with its wooded surroundings. A private courtyard with outdoor seating is visible, along with lush greenery and carefully placed stones that enhance the natural landscape.

4.86 out of 5 average rating, 247 reviews

Brand New Modern Cabin walk to town

This brand new cabin was built using green construction and features a living green roof. It is an open concept 1 bedroom with all new fixtures and a soaking tub. You can walk to town in approximately 10-12 minutes. This is in a neighborhood so there are visible neighbors but the architect utilized the natural surroundings to make it feel like you are in the woods. The beauty of this house is it’s access to town. If you look at my past reviews it’s the same location but a new house in front.

4.82 out of 5 average rating, 201 reviews

The charming green cottage is surrounded by lush trees and landscaped gardens. A stone pathway leads to the entrance, and several shrubs have been planted alongside the path, enhancing the natural setting. Soft grass covers the area in front of the house.

Cabin in Bearsville

The CubHouse NEW Barrel Sauna at foot of Mountain

WOODSTOCK/BEARSVILLE Escape to a little healing magic in this 1909 built cottage. Originally owned by a medicine woman in the early 1900s. This home has charm(s) of an enchanted past and it has been renovated to provide a modern, cozy experience. -Wood burning fireplace -Projector w/screens inside & in screenhouse -Full kitchen -River and Mountain access -Propane grill -500 sq ft screen house (closed during winter months) Dog friendly but must be approved before booking. $25 per night fee

4.87 out of 5 average rating, 1,000 reviews

A cozy sleeping area features warm wooden paneling and a spacious bed topped with a striped blanket. A colorful, patterned cushion adds a pop of color. Framed artwork is displayed on the walls, with a warm glow from wall sconces illuminating the space.

Guesthouse in Woodstock

Rocket Room - Rock Stars Only

Walk to town, hiking or a swimming hole. A popular vintage look cabin that backs up to a private woods but is steps from all Woodstock has to offer. Long time superhosts. Turn on, Tune in, Drop out in our 70's rock & roll hideaway carved out of a converted 1920s carriage house. This ain't your Grandma's cabin. All our units have been featured in videos, films, and photoshoots. This one has been featured in Playboy and Imperial Publishing arthouse book. Town of Woodstock OP #27.54-1-12

The image shows the exterior of a wooden cabin surrounded by trees. A bright yellow flowering bush is positioned near the entrance, enhancing the natural setting. The front door is framed by large windows, providing a welcoming ambiance.

4.96 out of 5 average rating, 192 reviews

Charming Artist Cottage

We welcome couples, solo adventurers, families and small dogs (sorry, no cats) to our year round cabin. Two BDRs (1 Q off LR1, 1 F off DR 1/2 wall w/privacy curtain, no door), full kitchen, screened-in porch, large LR with a stone fireplace, satellite internet & TV. Enjoy nature and a peaceful setting at the foot of Overlook Mt. on 6 wooded acres with a brook. Privacy, and 3 miles to Woodstock Village. Original art work from our grandfather Joseph Garlock adds to the charm of our cabin.

4.87 out of 5 average rating, 142 reviews

A charming cottage surrounded by lush greenery and trees is depicted. The exterior features a light-colored wooden facade with blue accents on doors and windows. A fenced area is visible, along with an herb garden that adds vibrant foliage in the foreground.

Cottage in Woodstock

Herb Cottage: history•art•woodstove•walk to town!

Experience the essence of Woodstock in this former home to Anita M. Smith — artist, historian and “Herb Lady of the Catskills.” Enjoy the fragrance and serenity of the “show-off” herb garden right outside your door. Just 1/2 mile from town center, Herb Cottage is nestled at the gateway to Woodstock’s legendary Overlook Mountain. If you’re searching for a mystical hideaway in which to relax, restore your energies, and recapture your creative self, this is the place for you!

A bright sunroom features a comfortable seating area adorned with patterned cushions. Large windows allow natural light to fill the space, complemented by a small lamp and a decorative rug with a floral design. A propane stove adds warmth, while potted plants bring a touch of nature inside.

4.9 out of 5 average rating, 182 reviews

Architect's Farmhouse in Woodstock

This rustic and cozy farmhouse is the perfect retreat from the city. Just a few minutes from the heart of Woodstock, the property feels secluded, quiet, and deeply relaxing. It’s a great spot for anyone looking for a true country farmhouse experience. This is a magical Woodstock retreat filled with rustic charm, eclectic furnishings, and modern comforts. A perfect place for families, groups, and anyone looking for a peaceful country escape.

4.97 out of 5 average rating, 105 reviews

A modern living space is showcased with a round dining table surrounded by six black chairs. A grey sofa is positioned next to a patterned area rug. Wall art complements the light wood beams above, while large windows let in natural light.

Townhouse in Woodstock

A Modern Hideaway in the Heart of Woodstock

A private, peaceful escape just off Woodstock's charming Tinker Street. This light-filled and beautifully designed space offers a perfect mix of comfort and quiet luxury. Whether you are seeking a recharge, access to hiking trails, or a quick getaway, we got you. Beyond the walls, you can enjoy refreshing nature as well as the vibrant art, music, and food scene Woodstock has to offer.

Popular amenities for Woodstock pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.9 out of 5 average rating, 251 reviews

The modern barn-style home is surrounded by lush greenery, featuring large windows that highlight its spacious interior. A wraparound deck with railings invites outdoor relaxation, while an inviting facade includes a prominent gabled entry. Soft lighting enhances the welcoming ambiance as dusk approaches.

Home in Mount Tremper

Stunning Modern Barn minutes from Woodstock 21N195

4.93 out of 5 average rating, 257 reviews

A two-story red cottage is nestled among tall trees, showcasing a classic design with multiple windows and balconies. A gravel driveway leads to the entrance, providing access to outdoor spaces. The surrounding wooded landscape adds to the cottage's natural setting.

Home in Bearsville

A Cozy’s Woodstock Getaway Home

A bright dining area features a long white table surrounded by wooden chairs. Large glass doors open to a deck with river views. Sunlight fills the space, highlighting the clean lines of the cabinetry and décor in soft, neutral tones.

4.93 out of 5 average rating, 181 reviews

Upstate Waterfront Saugerties Retreat-Near HITS

A rustic dining area features a large wooden table set for dinner with elegant glassware and vibrant flowers. Natural light pours in through expansive windows, creating a bright atmosphere that looks out onto landscaped outdoor space.

4.99 out of 5 average rating, 148 reviews

Whispering Pines: Secluded Retreat near town

4.98 out of 5 average rating, 108 reviews

A warm and inviting living space is seen, featuring a round wooden dining table surrounded by four rustic chairs. An adobe wood-burning fireplace is visible in the background, with seating arranged nearby for relaxation. Natural light flows in through a window, enhancing the cozy atmosphere.

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

A bright and airy living room features large windows allowing natural light to fill the space. A stylish sectional sofa in warm tones is arranged on a patterned area rug, complemented by a coffee table. Skylights enhance the openness, while artwork decorates the walls.

4.92 out of 5 average rating, 198 reviews

Fabulous Family House nr Woodstock Center

4.95 out of 5 average rating, 245 reviews

A two-person hot tub is situated outside, offering views of the surrounding landscape and Ashokan reservoir. A blossoming tree stands nearby, and comfortable seating is positioned on the lawn, enhancing the outdoor experience. The sky reflects shades of blue and soft clouds.

Home in Hurley

Hot tub with stunning views, 5 min to Woodstock

A spacious living area features a charcoal sofa paired with a sleek black armchair. Natural light streams through large windows, illuminating an art piece above a wooden coffee table. A wood-burning stove adds warmth, complemented by a stack of logs nearby.

4.92 out of 5 average rating, 213 reviews

Escape to Pine Lane

Pet-friendly home rentals with a pool

Guesthouse in Olivebridge

A charming red cottage is set against a backdrop of lush greenery and blue skies. The landscaped yard features well-maintained grass and a variety of trees, providing a serene outdoor environment. Nearby, an additional outbuilding is visible, enhancing the rustic atmosphere.

4.93 out of 5 average rating, 280 reviews

Sweet Fern Cottage With Saltwater Pool

The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.

4.94 out of 5 average rating, 144 reviews

Bluestone Escape - Where everyone is at home.

4.89 out of 5 average rating, 187 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

A panoramic view of distant mountains stretches under a clear blue sky. The landscape features a mix of trees and open areas, showcasing the natural beauty of the surroundings.

4.87 out of 5 average rating, 145 reviews

Gorgeous Villa MntnViews, nr SKI, firepl, hot tub!

A tranquil saltwater pool is set against a natural stone backdrop, surrounded by lush greenery. Poolside, a sunbed and umbrella are positioned, providing a relaxation spot. The patio features a rugged stone surface, enhancing the outdoor experience amidst a serene atmosphere.

4.89 out of 5 average rating, 117 reviews

Highwoods Haven | saltwater pool and hot tub

5 out of 5 average rating, 103 reviews

An aerial view of BoHo Farm House showcases a modern black exterior with expansive glass panels. The garden features a swimming pool surrounded by lounging chairs and a fire pit, set against a backdrop of lush green grass and trees.

Home in Accord

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

A clear blue in-ground swimming pool is surrounded by a patio area featuring lounge chairs and umbrellas. Lush green trees are visible in the background, providing a natural backdrop. A wooden deck extends from the farmhouse, adding to the outdoor space.

4.94 out of 5 average rating, 165 reviews

5BR Retreat w/ POOL Near HITS Saugerties & Hunter

4.95 out of 5 average rating, 230 reviews

Cabin in Shandaken

4Br l Fire-pit l Hot Tub l 10 min to Belleayre

Private, pet-friendly home rentals

4.95 out of 5 average rating, 222 reviews

An outdoor area is visible through a large window, featuring a vintage clawfoot bathtub and a wooden stool. A hammock is suspended nearby. Lush greenery surrounds the space, creating a serene atmosphere.

Home in Spring Glen

Creekside cottage on 65 acres of land

4.97 out of 5 average rating, 142 reviews

Cabin in Shandaken

Cozy Creekside Cabin: Ski Days, Fireside Nights

A tranquil cabin is surrounded by lush greenery, with a stone pathway leading to its inviting entrance. Large windows reflect the natural light and provide views of the vibrant landscape. The natural wood siding blends harmoniously with the serene forest setting.

4.97 out of 5 average rating, 159 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.

4.98 out of 5 average rating, 179 reviews

The Stone House

4.92 out of 5 average rating, 112 reviews

A vibrant flower garden features a mix of white, pink, and red blooms, positioned in front of a wooden railing. Beyond the garden, a serene stream flows gently through a wooded area, accented by lush greenery and a partly cloudy sky above.

Cabin in Phoenicia

Mountains and Rivers, Secluded Cabin

A spacious yellow house is surrounded by lush greenery and well-maintained shrubs. A wooden porch with steps leads to the front door. The sky is clear and blue, providing a bright and inviting backdrop.

4.86 out of 5 average rating, 124 reviews

CAPE ESCAPE IN THE MOUNTAINS

5 out of 5 average rating, 124 reviews

A fire pit is surrounded by wooden adirondack chairs, creating a cozy outdoor seating area. Behind, a spacious deck is adorned with string lights, illuminating the trees and grassy area, enhancing the inviting atmosphere of the secluded surroundings.

Cabin in Willow

Mountain Home with firepit and breathtaking views