Holiday rentals in Woodstock

4.91 out of 5 average rating, 705 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, 388 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

Superhost

Cabin in Woodstock

4.85 out of 5 average rating, 210 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.

4.94 out of 5 average rating, 301 reviews

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, 350 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.

4.87 out of 5 average rating, 935 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, 163 reviews

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, 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, 472 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.

4.99 out of 5 average rating, 115 reviews

Idyllic Forest Home

As featured in Atomic Ranch & Country Home Magazines, the Maverick is a secluded luxuriously restored 1964 MidCentury deck home furnished with Eames and other iconic era furnishings. The home was built for television pioneer, Mary Sinclair. The Maverick is secluded yet just 5 minutes from downtown Woodstock as well as beautiful hiking, running, and biking trails. The home is perfectly set up for indoor | outdoor entertainment & dining.

4.94 out of 5 average rating, 363 reviews

Guest suite in Woodstock

Perfect Woodstock Location- Short Walk to Town

Perfect location! Short walk (350 yards) to center of Woodstock yet enjoy Catskill mountain and meadow views from home and patio in a serene private setting. NO CAR NEEDED. Easy Walk to bus stop, dining, shopping, flea market, farmer's market and movie theater. Close to hiking trails, swimming holes and beautiful forests. Security deposit is not charged upfront. Registered with town of Woodstock #19H-013.

Holiday rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Woodstock holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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 stars1 week 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.

5 out of 5 average rating, 41 reviews

Woodstock Carriage House

BeccaRating, 5 stars1 week ago

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

5 out of 5 average rating, 38 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

BingRating, 5 stars1 week ago

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

4.97 out of 5 average rating, 150 reviews

Cabin in Woodstock

Pet Friendly Cabin Doh-Ray up at 1450 ft

MariaRating, 5 stars1 month ago

This is the place to go if you want to be immersed in nature. You are definitely in the woods and surrounded by lush green. There is a pond glistening in your view from the back screened in porch. A lovely spot to have a curl up with a good book.!

5 out of 5 average rating, 11 reviews

Modern & Private Cottage Minutes From Woodstock

WilsonRating, 5 stars3 weeks 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 :)

4.9 out of 5 average rating, 585 reviews

Cabin in Woodstock

The Pike Lane Cabin & Nature Preserve

ArianaRating, 5 stars2 weeks ago

We've been visiting Darin's place for years and always find it so peaceful and lovely! The hosts are amazing, the land is beautiful, and the cabin is cozy, close to town and our favorite hikes. Can't wait to be back again soon!

5 out of 5 average rating, 29 reviews

Grandma's Place an Easy Walk to Woodstock -1 Queen

AnneRating, 5 stars2 weeks ago

My partner and I stayed at Hana’s place for two nights, to get away from the city. This was exactly what we were looking for: peaceful and quiet while within walking distance from Tinker street and other things to do around Woodstock. Haha made sure that nothing was lacking and that we felt right at home, which we definitely did. It was clean, quiet, and we will miss having our morning coffee in the backyard. We would absolutely return!