Apartment holiday rentals in Woodstock

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Top-rated apartment rentals in Woodstock

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Top guest favourite
A dining area features large windows bringing natural light, complemented by wooden benches and a table made of rustic wood. Shelves hold various plants and decorative items, adding a touch of greenery to the space. A vintage cabinet is placed against the wall.
Flat in Kingston
4.97 out of 5 average rating, 782 reviews

Vintage-Inspired Revitalized Historical Bau Guesthaus, A

Re-capture the allure of the past while indulging in modern luxury in this home originally built in the 1890s. The residence showcases original detailed ceilings, a mid-century design aesthetic, repointed original brick, and bright splashes of color. Entire 900sqf 1st floor unit. Includes 1 bedroom(Queen), private kitchen/dinning room, living room and a bathroom. The townhouse is restored with beautiful, vintage details but also with all the comforts of modern living like high speed Wifi, digital thermostats and entry to the home via smart lock. *additional one time fee of $25 to set up air mattress for 2 guests. All guests are welcome to use all facilities on our property; including our backyard. The property is centrally located in the heart of historical uptown Kingston. Explore the weekend farmers market just steps from the front porch, as well as local cafes, restaurants, museums, and music venues. The Bau Guesthouse is easily accessible. It is 7min walk from the Kingston Trailways bus stop and 5min drive from I-87 throughway exit 19. Parking on our street is metered Monday - Friday 9am to 5pm. Also free street parking is available just around corner from us.

Top guest favourite
A cozy bedroom features a spacious bed with layered bedding. A gallery wall of framed art pieces adds visual interest. Natural light filters through a window with shutters, illuminating the warm wood floors. An electric fireplace and a potted plant provide a touch of comfort.
Flat in Kingston
4.97 out of 5 average rating, 351 reviews

The Ivy on the Stone

The oldest house you can stay at in the historic heart of Kingston! Walkable! This landmark 1680 stone house has been featured in Upstate Diary and Houzz. Enter this 350 sq ft luxe apartment through a secret garden and a shared porch. The private spa-like bathroom features a clawfoot tub, and rain shower. Featuring an organic queen bed, an electric fireplace, workspace, William Morris wallpaper, and a Nespresso maker. If you want to stay in the larger house visit: https://abnb.me/EexspArCAIb

Top guest favourite
A single-story red house is set amidst lush greenery, featuring a well-maintained lawn. Large windows provide views of the surrounding trees. The property includes a deck and is situated in a quiet, spacious area.
Flat in Woodstock
4.99 out of 5 average rating, 178 reviews

Redbird 1926

A charming one 1 BR apartment attached to our home with a private deck. Entrance to deck and apt. is up eight stairs. Located in a quiet country setting 5 min. from the center of Woodstock and 15 min. from Kingston. This lovely apt. includes central A/C, WiFi, Roku, refrig., outdoor gas grill, microwave, toaster, coffee maker, sink, counter top electric burners, no oven. The bedroom has queen size bed. LR has a day bed for added sleeping space. Come spend time in a tranquil setting.

Top guest favourite
The open living area features tall windows that provide ample natural light. A comfortable sofa is situated beside a wooden coffee table, with a dining table set for four in the background. Modern appliances and a stylish ventilation hood enhance the kitchen space.
Flat in Kingston
4.97 out of 5 average rating, 157 reviews

DeMew Place

Enjoy the historic Rondout district of Kingston while relaxing in this beautiful, one-bedroom, one bath unit on the first floor of a brick building from 1900. Historic charm meets modern amenities, with 12' ceilings, in-floor heating, and an open concept kitchen, living and dining area across the street from the Hideaway Marina on the Rondout Creek. Take a relaxing walk along the water to the historic waterfront area on Broadway for dining, shopping or a boat ride on the Hudson River.

Top guest favourite
A rustic bench is positioned along a wooden fence, offering a vantage point of rolling hills adorned with autumn foliage. The scene captures a bright, open sky dotted with fluffy clouds, enhancing the natural beauty of the surrounding landscape.
Flat in Marlboro Township
4.97 out of 5 average rating, 429 reviews

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Guest favourite
Flat in Saugerties
4.97 out of 5 average rating, 128 reviews

Main St. Apt (2-3 bedrooms) with Outdoor Space

Come enjoy our beautiful, comfortable home in a historic building (c 1900) in the village of Saugerties. The spacious and bright 2 to 3 bedroom apartment is located on Main Street, steps away from fantastic shops, restaurants and galleries. Enjoy a large private 2nd floor deck and a shared 1st floor garden. Note: The listed price is for up to 4 people in 2 bedrooms. If you would like to use the third bedroom please make the reservation for 6 people.

Top guest favourite
The warmly colored room features a cozy seating area with a woven coffee table and two cushioned sofas facing each other. Sunlight filters through the orange curtains, highlighting a vibrant floral arrangement on the table and the inviting bed with patterned bedding in the background.
Flat in New Paltz
4.98 out of 5 average rating, 512 reviews

The Treehouse, lush Parisian inspired Studio

The Treehouse, a lush Parisian inspired Studio high in the treetops in the heart of the village of New Paltz. Private entrance leading to private rooftop deck, lovely sun filled space to enjoy the treescape or sunset. The Treehouse strives to be more than a place to sleep. If you’re looking for a place that will move your heart as well as place to call home while staying in New Paltz please consider The Treehouse.

Guest favourite
A well-lit entryway features wooden stairs leading up to a hallway. Light-colored walls and warm wooden flooring create a welcoming atmosphere. A decorative runner rug lies on the steps, and light fixtures above enhance visibility. Doorways at the top of the stairs lead to additional spaces.
Flat in Woodstock
4.89 out of 5 average rating, 450 reviews

Nook above the Pub!

1-bedroom, above the historic Woodstock Pub. Full Futon, able to accommodate 3 people. On local and Trailways Bus lines. Walk to shops, restaurants & The Colony. Plenty of hiking trails, skiing, kayaking, music, theatre, etc. Noise from pub below on weekends fluctuates. Bar/restaurant last seating at 9pm Fri/Sat. $10 food voucher, courtesy of your hosts. Twin mattress available on request for extra guest. $25 fee.

Guest favourite
Flat in Stone Ridge
4.91 out of 5 average rating, 571 reviews

Historic Loft in Stone Ridge near the Gunks

Stay in the upper level of a historic 1920 Hudson Valley farmhouse at the crossroads of Stone Ridge. This cozy second-floor retreat offers a peaceful base for exploring the Rondout Valley, with nearby hiking, historic hamlets, and scenic country drives. Perfect for guests who want a quiet Hudson Valley stay with authentic character and easy access to the region’s outdoor adventures.

Top guest favourite
A living area features a large stone hearth with distinctive brickwork and wooden beams overhead. A cozy seating area includes a modern sofa and a wooden coffee table. Natural light floods the space, complemented by green plants and a decorative chair for additional seating.
Flat in Kingston
4.96 out of 5 average rating, 637 reviews

Colonel Hasbrouck’s 1735 Stone House, Garden Level

Right in Kingston's historical Stockade District, this garden-level apartment blends original 18th-century decorative features like dutch doors and a large stone hearth with modern amenities like a washer/dryer and easy keyless entry. It's part of the Colonel Abraham Hasbrouck House, a registered historical landmark built in 1735.

Guest favourite
A spacious kitchen features white cabinetry topped with a grey speckled countertop. Four black bar stools line the kitchen island. Modern appliances, including a stainless steel refrigerator and a gas stove, are visible, while ample natural light enters through the windows, brightening the room.
Flat in Kingston
4.95 out of 5 average rating, 155 reviews

Huge Luxury Retreat- Walk To Uptown Kingston

Escape to this beautifully renovated, oversized Kingston retreat just steps from vibrant Uptown restaurants, shops, galleries, and historic charm. With nearly 3,000 sq ft of stylish living space, this rare property offers the space, comfort, and privacy that most rentals simply can’t match.

Guest favourite
A dining area showcases a round wooden table set with dishes and glasses, accompanied by green chairs. A cozy sofa and an armchair are positioned against the wall, while light streams through large windows, illuminating the warm wood flooring.
Flat in Catskill
4.96 out of 5 average rating, 293 reviews

Above SpringRise

Newly renovated, top floor apartment on Main Street in the historic district of Catskill. Overlooking both the Catskill Creek and the Catskill Mountains, this floor-through apartment is just 10 minutes to Hudson, 5 minutes to three Nature preserves and 15 minutes to Kaaterskill Falls.

Popular amenities for Woodstock apartment rentals

Quick stats about flat rentals in Woodstock

  • Total holiday rentals

    Explore 20 holiday rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 1,710 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Woodstock holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodstock rentals

  • 4.8 Average rating

    Woodstock stays are highly rated by guests – averaging 4.8 out of 5!

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