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Cottage holiday rentals in Woodstock

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Quick stats about cottage rentals in Woodstock

  • Total holiday rentals

    Explore 20 holiday rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at $204 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,370 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Woodstock holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodstock rentals

  • 4.9 Average rating

    Woodstock stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated cottage rentals in Woodstock

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Guest favourite
A spacious living area features two modern armchairs with orange accent pillows facing a large picture window. The serene view of the wooded area surrounding the private pond is visible, inviting natural light into the space. A low coffee table occupies the center, complemented by a soft sofa nearby.
Cottage in Saugerties

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

Kick back and relax in this calm, stylish space, with private wildlife filled pond & cowboy pool This house is great for a family, or two couples. There are lots of relaxing spaces inside and several seating areas in nature outside. Ten minutes to the towns of Woodstock and Saugerties, you will have the perfect location to enjoy the best experiences the Hudson Valley has to offer. This 4 bedroom, 3 bath house has been recently gut renovated. Enjoy the beautiful design and natural landscape.

4.97 out of 5 average rating, 173 reviews
Top Guest favourite
A sparkling heated pool is framed by natural surroundings, with a stand-alone guest house visible in the background. Lush trees create a serene atmosphere, enhancing the privacy of the outdoor space. Nearby, seating areas and open grass provide inviting spots for relaxation.
Cottage in Bearsville

Contemporary Guesthouse with Heated Pool

Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

4.97 out of 5 average rating, 148 reviews
Top Guest favourite
A red house with yellow trim features a welcoming front porch and multiple windows. The porch is accessed by a set of steps and surrounded by a well-maintained yard with trees and shrubs, providing a charming entryway.
Cottage in Woodstock

Woodstock Dog Friendly Cozy Cottage in Town + 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!

4.85 out of 5 average rating, 302 reviews
Guest favourite
A charming wooden cottage is set amidst lush greenery, featuring a welcoming entrance framed by low shrubs. The cottage's sloped roof and large front door invite guests into a serene environment, surrounded by trees and open space.
Cottage in Woodstock

Woodstock Mountain Cottage w/ Swimming Pool

This romantic 2 bed cottage has large beamed ceilings, fully stocked kitchen, bathtub, mountain views, and hiking trails. We use strict cleaning protocols to ensure each stay is perfect and feels like home. The house is equipped with fast wifi and a ROKU Ultra for your tv needs! Located just 3 mins to the center of Woodstock. Swim in the pool, hike a trail, enjoy nature, grill or relax in the hammock. Pool is shared only with hosts & very private. No guests of guests allowed & no parties.

4.83 out of 5 average rating, 133 reviews
Guest favourite
An open-plan kitchen and dining area features a large wooden table surrounded by several chairs. A modern kitchen with dark cabinetry and stainless steel appliances is seen in the background. A wood stove is positioned near the window, which offers views of the snowy outdoor scenery.
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.

4.94 out of 5 average rating, 385 reviews
Top Guest favourite
An open-plan living area is illuminated by natural light from expansive sliding glass doors. A small dining table with two chairs sits beside the doors, while a full kitchen and refrigerator are visible in the background. Light wood flooring contrasts with a woven area rug.
Cottage in Woodstock

Mountain views, mid-century style! 1 mile to town.

Spacious, stylish, light filled studio guesthouse with gorgeous mountain views on 4 acre estate. Wake up to a view of the Catskills, seen through an expanse of sliding glass doors. Eat breakfast on the balcony, or relax on the couch while watching the sun go down. Inside: luxuriously comfortable, eco-friendly queen mattress, 50" smartTV, full kitchen, full bath. Outside: picnic table, hammock, cascading brook, land to explore. Good wifi inside/outside. (Woodstock STR permit #23H-279).

4.93 out of 5 average rating, 166 reviews
Top Guest favourite
A cottage is presented with a warm wooden facade, surrounded by lush greenery. A small porch is accessible from the front entrance, and landscaping features tidy garden beds with a variety of plants. Dense trees provide a natural backdrop, enhancing the tranquil setting.
Cottage in Woodstock

Woodstock Streamside Cottage

Our streamside cottage is located on a five acre property under a mile to the center of Woodstock. The Sawkill Stream is your backyard with plenty of beautiful trees and meadows your front yard. Quiet sounds of the stream and nature surround you. Central heat and central a/c keeps you comfortable year round. Newly renovated. Please read our reviews and see how you'll feel. About 1.5 miles from the Ramble concert venue and 2.5 miles from the Bearsville Theater area. Enjoy!

4.95 out of 5 average rating, 331 reviews
Top Guest favourite
A charming cottage exterior is framed by lush greenery. The entrance is marked by a fenced patio area with a gravel path leading to the door. Potted plants add a touch of greenery, while a shaded seating area with a fire pit invites relaxation.
Cottage in Woodstock

Luxury+firepit+stream+walk/town=Brook Cottage Too

Brook Cottage Too occupies the west wing of a newly-renovated 1928 Woodstock artist’s cottage featuring: oversize north-light windows; skylights; 1 bedroom w/king bed; spa-like bathroom; newly-remodeled kitchen; fire stove; bluestone patio w/gas grill + firepit; AC. Ideally located at the end of a private lane on a spacious shared property bordered by a year-round stream + conservation land. Immaculately clean + available for long-term rentals, as well as short-term stays.

4.99 out of 5 average rating, 204 reviews
Top Guest favourite
A charming cottage sits nestled in green surroundings, featuring a front porch with two inviting chairs. A spacious lawn leads up to the entrance, framed by trees that provide natural shade. Light filters gently through the foliage, accentuating the peaceful setting.
Cottage in Woodstock

Hidden Pines - Downtown Woodstock by Millstream!

Two blocks from Downtown Woodstock tucked away on a quiet lane sits Hidden Pines, a classic Woodstock Cottage. No need for a car here! Spacious light filled rooms and a bluestone terrace provide a soothing respite. Stroll down for a swim at the Millstream which is 1/2 block away. This cottage has been lovingly renovated and includes Central AC and heat. Please note this is a guest house. The main house is quietly owner occupied with its own private separate side yard.

4.91 out of 5 average rating, 541 reviews
Top Guest favourite
A cozy cottage is set within a wooded landscape, featuring a combination of black exterior and a warm wooden porch. Four Adirondack chairs surround a fire pit, with colorful plant arrangements enhancing the natural setting among fallen leaves.
Cottage in Bearsville

Mirror Moon Cottage (waterfront)

Mirror Moon cottage is a newly renovated, original 1960's cottage in the heart of a historic arts and music community. The property is waterfront, overlooking the Saw Kill, with tranquil views & sounds. Imagine falling asleep to the sounds of the river on our hammock. Only an 8 min bike ride, or 4 min drive to the center of Woodstock town. It's subtly tucked into the woods, just outside of town. Perfect for a friends or couples getaway! Make yourself at home!

LocationComfortSleep quality

4.96 out of 5 average rating, 266 reviews
Top Guest favourite
The inviting living area features a comfortable gray sofa adorned with accent pillows. A wooden coffee table is centrally placed, while a modern lamp and a cozy rug enhance the space. Large sliding doors open onto the deck, offering natural light and views of the surroundings.
Cottage in Chichester

Stream Come True | Hot Tub, Ski, Hike, Relax

Welcome to Flowing Water, a peaceful streamside cottage in the heart of the Catskills where the sound of rushing water and rustling trees melts stress away. Just minutes from Phoenicia and a short drive to Woodstock, Hunter, and Belleayre, it’s the perfect retreat for skiing, hiking, stargazing, or simply relaxing. Enjoy a hot tub or the firepit under the stars, a wood stove, streamside deck, and peaceful vibes year-round.

4.94 out of 5 average rating, 153 reviews
Guest favourite
A light-filled corner of the cottage features a wooden dining table with orange metal legs and two chairs. A vase of fresh flowers sits on the table, and sunlight streams in through nearby windows, illuminating the simple decor.
Cottage in Saugerties

Blue Mountain Cottage

Enjoy the best of the Catskills from Blue Mountain Cottage. The cottage is 5 minutes from many mountain trails, 12 minutes to Woodstock, 10 to Saugerties, under 30 to Hunter Mountain and 20 to Kingston. This area has so much to offer in all four seasons! We are just down the road from Indian Head Wilderness in Catskill Park, and very close to Kaaterskill Wild Forest.

4.94 out of 5 average rating, 298 reviews

Popular amenities for Woodstock cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top Guest favourite
The entrance of a cottage is framed by lush greenery, showcasing a welcoming wooden porch and a dark door. Potted plants add a touch of charm to the inviting pathway, which leads through a grassy yard.
Cottage in Boiceville

Catskills Woodstock Design Retreat w/ hot tub

4.97 out of 5 average rating, 138 reviews
Top Guest favourite
The inviting exterior of a cozy cabin is surrounded by lush greenery, with warm lights illuminating the covered porch. A fire pit is featured at the forefront, surrounded by four Adirondack chairs, creating a welcoming space for evening gatherings.
Cottage in Kerhonkson

Ye Little Wood | Cozy Forest Cottage with Hot Tub

5.0 out of 5 average rating, 250 reviews
Top Guest favourite
A spacious studio features a renovated ceiling with wooden beams and skylights. Large glass doors provide access to the outdoor area. Colorful textiles embellish the seating area, while a dining table is set with place settings. A kitchenette is visible in the background.
Cottage in Phoenicia

Romantic hot tub cottage. Hiking/breweries nearby.

4.9 out of 5 average rating, 963 reviews
Superhost
A wooden deck is furnished with comfortable seating and a coffee table, providing a serene view of rolling mountains and a tranquil pond. The sky is filled with fluffy clouds, reflecting warm hues as the sun sets, enhancing the natural beauty of the landscape.
Cottage in Denver

Country Cottage w/ HOT TUB & Views

4.92 out of 5 average rating, 174 reviews
Guest favourite
A living area features a cozy gas fireplace framed by a white mantel. Comfortable seating is provided with a gray armchair, vibrant red chairs, and a green ottoman in the center. A dining table for two stands to one side, with artful wall decor enhancing the ambiance.
Cottage in Town of Gilboa

Home Alone Mountain

ComfortHot tubHospitality

4.92 out of 5 average rating, 399 reviews
Guest favourite
Two bright orange Adirondack chairs are positioned on a deck overlooking a serene creek, accompanied by a stainless steel fire pit. Lush greenery frames the view, creating a peaceful outdoor space ideal for relaxation or social gatherings.
Cottage in High Falls

Waterfront 3 Bdrm. w/ Hot Tub & Outdoor Fire Pit!

4.96 out of 5 average rating, 85 reviews
Top Guest favourite
An open living area features a contemporary design with soft seating and a glass coffee table. A large, colorful artwork adorns the wall, while natural light enters through multiple windows. A dining table with chairs is visible in the background, complemented by a light-colored rug.
Cottage in West Shokan

Ashokan ArtHaus, Private Hot Tub, Wags Welcome!

4.97 out of 5 average rating, 32 reviews
Top Guest favourite
A charming single-story house is set against a partly cloudy sky. The exterior features light-colored siding and a welcoming front porch with steps leading up. A manicured lawn with green shrubbery surrounds the home, and a two-car garage is visible to the left.
Cottage in Kingston

Charming Cottage in Kingston - License #002740

4.94 out of 5 average rating, 71 reviews

Pet-friendly cottage rentals

Top Guest favourite
The exterior of the house showcases a charming two-story structure with light siding and a vibrant red front door. Lush greenery surrounds the property, complemented by a well-maintained lawn and a pathway leading to the entrance.
Cottage in Port Ewen

Swan Cottage with Expansive Hudson River Views

4.99 out of 5 average rating, 192 reviews
Top Guest favourite
Cottage in West Camp

Hudson Valley Cottage

4.94 out of 5 average rating, 143 reviews
Top Guest favourite
A comfortable living area presents a sectional sofa, accent chairs, and a wooden coffee table. Large windows allow natural light to fill the space, while a decorative area rug adds warmth. A small stove is positioned for added coziness, and colorful artwork adorns the walls.
Cottage in High Falls

The Carriage House

4.98 out of 5 average rating, 139 reviews
Top Guest favourite
A rustic cottage is surrounded by greenery, featuring a spacious wooden patio equipped with two blue Adirondack chairs. Large windows offer views of the outdoor area, and a sloped roof complements the design. Nearby trees provide shade and a natural setting.
Cottage in Chichester

Peaceful Cottage With Mountain Views

4.93 out of 5 average rating, 126 reviews
Top Guest favourite
A cozy living area features a black sofa adorned with patterned throw pillows and a warm blanket. A wooden coffee table sits in front, complementing the space. In the background, a kitchen with bar stools is visible, along with a window allowing natural light.
Cottage in Saugerties

Chic & Cozy Cottage 10 mins to Woodstock

4.94 out of 5 average rating, 317 reviews
Top Guest favourite
Cottage in Elka Park

The North Nook-Mtn Views, 5 min to downtown,hiking

4.97 out of 5 average rating, 151 reviews
Top Guest favourite
A stone patio is surrounded by vibrant flowers and greenery, featuring a wooden table with four chairs. The cottage's large window provides a view of the inviting outdoor space, where additional potted plants add a touch of color and natural beauty.
Cottage in Chichester

Garden Cottage In The Catskills

4.99 out of 5 average rating, 656 reviews
Guest favourite
A cozy living area showcases a brown sofa adorned with decorative pillows, complemented by a patterned area rug. A rocking chair sits nearby, and a wooden table holds a stack of books. Natural light enters through two windows featuring bamboo shades.
Cottage in Phoenicia

Cozy Catskill Cottage on the Pantherkill

4.95 out of 5 average rating, 350 reviews

Private cottage rentals

Top Guest favourite
A spacious living area features a light-colored couch adorned with blue, green, and yellow pillows. A round coffee table sits in front of it, complemented by a rocking chair in green. A bright yellow wall and large windows enhance the room's openness.
Cottage in High Falls

Leggett Cottage

4.93 out of 5 average rating, 290 reviews
Top Guest favourite
A modern living area features a dark sectional sofa and a cozy coffee table, surrounded by an array of artwork on the walls. A large window allows natural light to illuminate the space, while a patterned rug adds warmth to the concrete floor.
Cottage in Bearsville

Coldbrook Cottage

4.99 out of 5 average rating, 198 reviews
Top Guest favourite
A rustic cottage is surrounded by lush greenery, featuring a wrap-around deck illuminated by string lights. The wooden structure is complemented by various plants and shrubs, offering a serene and inviting atmosphere. The entry is adorned with a partially covered porch, enhancing the cottage's natural charm.
Cottage in Phoenicia

Charming creekside cottage in Phoenicia

4.94 out of 5 average rating, 317 reviews
Top Guest favourite
A charming cottage exterior features light blue siding with white trim and a front door painted in a soft green. Large windows allow natural light to illuminate the inviting entryway. Lush greenery and colorful blooms enhance the tranquil surroundings.
Cottage in Phoenicia

Phoenicia Getaway (up front pricing)

4.94 out of 5 average rating, 236 reviews
Superhost
Cottage in Bearsville

WOODSTOCK COOPER LAKE COTTAGE

4.8 out of 5 average rating, 174 reviews
Guest favourite
The garden area showcases a charming cottage entrance framed by greenery. A dining set beneath strung lights invites outdoor dining. A propane grill stands nearby on a stone path, complemented by flowers in pots, adding a touch of color to the serene background.
Cottage in High Falls

Historic cottage near Mohonk & Minnewaska, 2BR/2BA

4.92 out of 5 average rating, 119 reviews
Guest favourite
A serene lake view is captured at sunset, showcasing a vibrant sky filled with shades of pink and orange reflecting on the calm water. The surrounding landscape includes gentle hills and trees, adding depth to the tranquil scene.
Cottage in Ulster Park

Romantic House on a Magical Lake

4.92 out of 5 average rating, 207 reviews
Top Guest favourite
Cottage in Rosendale

Modern cottage beneath a rock ledge

4.99 out of 5 average rating, 527 reviews

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$353 NZD$348 NZD$339 NZD$338 NZD$370 NZD$351 NZD$377 NZD$348 NZD$366 NZD$373 NZD$395 NZD$361 NZD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

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