Holiday rentals with outdoor seating in Woodstock

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Woodstock

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Home in Woodstock

4.91 out of 5 average rating, 640 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.

19–26 Nov

$239 NZD per night

Guest favourite

Home in Woodstock

4.94 out of 5 average rating, 268 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.

10–17 Nov

$1,238 NZD per night

Guest favourite

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 300 reviews

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. We use fragrance free laundry detergent. No smoking or vaping. This listing is not suitable for children or infants.

1–8 Jan

$225 NZD per night

Guest favourite

Guesthouse in Woodstock

5.0 out of 5 average rating, 300 reviews

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

PRIVATE Modern/Rustic Apt WALK TO ALL 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 on deck 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

1–8 Apr

$431 NZD per night

Guest favourite

Apartment in Woodstock

4.99 out of 5 average rating, 136 reviews

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.

31 Aug – 7 Sep

$229 NZD per night

Guest favourite

Guesthouse in Woodstock

4.86 out of 5 average rating, 831 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

12–19 Jan

$231 NZD per night

Guest favourite

Guesthouse in Olivebridge

4.96 out of 5 average rating, 225 reviews

Black Olive Cabin in the Woods - Secluded, Tiny

The cabin is nestled into a mossy rock ledge covered with ferns in a secluded part of the Catskills just south of the Ashokan Reservoir. Constructed of large reclaimed hemlock beams and charred cedar siding on the outside, the cabin mixes the old with the new. The open concept design includes high ceilings, hardwood floors, a wood stove, lofted sleeping quarters, a full bathroom, and a kitchen with an induction cooktop and convection oven. It's the perfect weekend getaway.

27 Sep – 4 Oct

$263 NZD per night

Guest favourite

Cottage in Saugerties

4.93 out of 5 average rating, 217 reviews

Chic & Cozy Cottage 10 mins to Woodstock

Located on a bucolic country road on the border between Saugerties and Woodstock, this newly renovated 500 sq ft cottage is on a private acre filled with spaces to relax: screened in dining shed, fire pit, BBQ grill, a creek, forest & the magical sound of a hidden waterfall across the road. Just 10 min from Woodstock town square, 8 min to Levon Helm Studios, and 15 from Bearsville Theater, it's the perfect escape. (Pets welcome on a case by case basis. Please ask.)

9–16 Apr

$255 NZD per night

Superhost

Barn in Woodstock

4.84 out of 5 average rating, 166 reviews

The Woodstock Barn Studio

Once a Woodstock chicken barn, your space is the lower level,of a renovated studio apt. that maintains its rustic charm with wide plank pine floors & ceiling beams. Only 2 blocks to down town Woodstock & bus stop to NYC . There are hiking trails for you to enjoy, the beautiful Wilson State Park as well as The stunning views of Cooper Lake, the Ashokan Reservoir & Rail Trail that will help sooth your spirit. Bring your camera! Well behaved pets welcome.

24 Jun – 1 Jul

$214 NZD per night

Guest favourite

Tiny home in Saugerties

4.94 out of 5 average rating, 218 reviews

Gorgeous Tiny House with Mountain View

Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! “The Haven” at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

11–18 Apr

$216 NZD per night

Guest favourite

Cabin in Boiceville

5.0 out of 5 average rating, 122 reviews

Come enjoy our wee cabin!

Our Wee Cabin is 25 mins to Belleayre and ready for your visit! Enjoy the bucolic view, modern yet cozy decor and convenient location while you explore the beautiful Catskills. Our Wee Cabin has a full kitchen & bathroom and a bedroom with a Queen-sized bed. Town of Olive Short Term Rental permit Registration No: STR-22-15 Please note: Property shared with another Airbnb: Our Wee Cottage.

1–8 Sep

$294 NZD per night

Guest favourite

Cottage in Woodstock

4.99 out of 5 average rating, 277 reviews

Grapevine Cottage

DESCRIPTION Enter our private backyard on 2 1/2 acres by crossing your own bridge far above the forest floor overlooking a stream and waterfall, then meander along a stone path, entering your grape arbor and vegetable garden into your cottage. The gardens where featured in THE Wall Street JOURNAL Sept 11-12 2021

14–21 Dec

$418 NZD per night