Holiday houses in Woodstock

4.91 out of 5 average rating, 707 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.

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

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

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.

4.92 out of 5 average rating, 178 reviews

Villa in Woodstock

The Falls

A secret treasure in the heart of Woodstock. This waterfall escape is tucked up in the center of town with incredible privacy, a private deck overlooking the waterfalls and located on the entire first floor just up a flight of stairs of the main house. Enter through your own private deck overlooking the waterfalls. Walk to all the great restaurants, galleries and shops around Woodstock. A truly magical experience. amidst the trees on top of the waterfalls. The most sought after Airbnb in town.

Superhost

Cabin in Woodstock

4.85 out of 5 average rating, 213 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.

4.84 out of 5 average rating, 257 reviews

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!

4.99 out of 5 average rating, 160 reviews

Apartment in Woodstock

Redbird 1926

A charming one 1 BR apartment attached to the house with a private deck and entry. It's located in a quiet county area 5 min. from the center of Woodstock and 15 min. from Kingston. This lovely apt. includes central A/C, WiFi, Roku, refrig., microwave, toaster, coffee maker, sink- no stove, no oven. The BR has a new queen size bed and the LR has a day bed for added sleeping space. Come spend time in a tranquil setting. Picnic table and gas grill added to the side yard for your enjoyment.

4.96 out of 5 average rating, 351 reviews

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.

4.86 out of 5 average rating, 937 reviews

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

4.99 out of 5 average rating, 162 reviews

Guest suite in Woodstock

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

4.91 out of 5 average rating, 473 reviews

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.

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Popular amenities for Woodstock holiday rentals

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Free parking on premises

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Other great holiday rentals in Woodstock

4.96 out of 5 average rating, 81 reviews

Townhouse in Woodstock

A Modern Hideaway in the Heart of Woodstock

KaitlinRating, 5 stars2 weeks ago

Really fantastic property. The house is beautiful and very well kept. The owner’s honored the integrity of the farmhouse while the modern updated amenities make it a perfectly livable space. You’ll find privacy and peace in the back yard. The location is unbeatable. A must stay for Woodstock. Highly recommend.

4.95 out of 5 average rating, 270 reviews

Guest suite in Woodstock

Meadowsweet Woodstock

JenniferRating, 5 stars2 weeks ago

I have stayed here always for my getaways during the past few years. Just me. Remarkably you are so close to Woodstock proper but on one of the loveliest, bucolic and private streets around. Premises couldn’t be more lovely, squeaky clean or comfortable. Best is that the owners couldn’t be nicer. Dont hesitate to book as this home away from home does not disappoint.

5 out of 5 average rating, 41 reviews

Woodstock Carriage House

BeccaRating, 5 stars2 weeks ago

Lovely view, lovey people. It was an easy walk to restaurants and shops. Enjoyed my stay very much.

4.96 out of 5 average rating, 797 reviews

Treehouse in Willow

Willow Treehouse - secluded, unique, romantic

JunRating, 5 stars2 weeks ago

Willow Treehouse is everything we hoped for and more. Tucked away in the woods with a peaceful pond view, it feels like stepping into a dreamy world. The cabin is beautifully designed ：cozy, minimal, and full of charm. The giant window makes you feel like you’re living in the forest. Listening to jazz and old classics on vinyl while watching the sunset through the trees was pure magic. The outdoor hot tub was another highlight. soaking under the stars was unforgettable. There’s no Wi-Fi, which was actually a gift, it helped us truly unplug and be present.

5 out of 5 average rating, 38 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

AmandaRating, 5 starstoday

We had a serene and luxurious stay at Fil and Ellie’s. The inside of the home is comfortable and they seem to have thought of every detail. We so enjoyed the peace and quiet, the views of the beautiful trees, and our soaks in the tub. This felt like a private oasis- a true slice of heaven.

4.99 out of 5 average rating, 365 reviews

Cabin in Kingston

Come Stay in "The Shoe"

TorstenRating, 5 stars1 month ago

Wonderful stay in a lovely house with unique welcoming charm in a great location. The attention to detail made us feel at home. We loved the screened-in room. It felt like sitting in the woods without the mosquitos. Bruce was a super responsive host. Highly recommended.

5 out of 5 average rating, 12 reviews

Modern & Private Cottage Minutes From Woodstock

WilsonRating, 5 stars1 month ago

We had a great time! Great location close to the center of Woodstock — very functional and clean space, everything worked perfectly. Kitchen was well equipped too! Overall very well thought out and perfect spot in Woodstock :)