
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.
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.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Woodstock Mountain Cottage w/ Pool /Swim
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 all of your tv needs! Located just 3 mins driving to the center of Woodstock. Swim in the pool, hike a nearby trail, enjoy nature, grill or relax in the hammock. Pool is shared with hosts. No guests of guests allowed and no parties.

Mt. Wonder: Big Cozy Cabin with Wow View
Welcome to Mt Wonder. With a wood burning hot tub, this secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Ten min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2br 1ba cabin, cozy and spacious, with a unique magical feel. Mega amenities incl the tub, BBQ, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin cabin: "Wonders Never Cease"

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star
PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "PREMIER" 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

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.

Romantic luxury+stream+walk to town=Brook Cottage
Brook Cottage occupies the east wing of a newly renovated authentic 1928 artist’s cottage featuring: 2-story north light windows; cathedral ceiling with skylights; fireplace and fire stove; bluestone patio with gas grill and outdoor seating; newly remodeled cook's kitchen; luxury amenities. Ideally located at the end of a private lane on a spacious shared property bordered by a year-round stream and conservation land, walking distance to the center of Woodstock, the famous "colony of the arts".

Luxury A-Frame Cabin in the Woods with Sauna
🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

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

Hillside Views in Hudson Valley
Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Chic Country Apt in Woodstock, NY
This private apartment, with its own entrance, is attached to one end of our house. The apt door and our front door are separated by a long patio. Please be advised: We do not give discounts or refunds for issues related to inclement weather. If there are issues with your reservation, or last minute cancellations, that will be reviewed on a case by case basis with Airbnb. While we love kids and pets, we cannot accommodate them here. Our operating permit number is #20H-100

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.)
Popular amenities for Woodstock outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Modern Escape • Sauna • Firepit • Near Woodstock

Mindful Escape: Theater, Trails, Wood Stove

Upstate Waterfront Saugerties Retreat-Near HITS

MCM Oasis | EV | Hot Tub

ENTER HOME - Minimalistic style warm & inviting

Dutch Touch Woodstock Cottage

Grandma's Place an Easy Walk to Woodstock

Sweeping mountain views in Woodstock, NY
Apartment rentals with outdoor seating

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

Art Room at Old Stone Farmhouse

Modena Mad House

Escape to the gunks! Climb, bike and relax!

Escape to a Sleek, Serene Studio on the Riverbank

Sunset Garden Room in High Falls

Foothills of the Catskills

Garden apt with river views in downtown Kingston
Condo rentals with outdoor seating

Trailside At Hunter-Phase II-Hunter NY

Windham Condo

Hike Minnewaska + Walk to Rail Trail, Food, Drink

5-Star Lux Condo: Ski-In/Out, Heated Pool, Hot Tub

Ski on/ Ski off Country Condo Hunter Mountain

Hunter Mountain 2BR Condo - Steps to Ski Slopes!

Slopeside Condo with wood fireplace

MountainViews/PoolOpens6/27•10 MinToLakes•Farm
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $452 NZD | $449 NZD | $443 NZD | $433 NZD | $450 NZD | $447 NZD | $492 NZD | $494 NZD | $476 NZD | $490 NZD | $485 NZD | $494 NZD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Quick stats about holiday rentals with outdoor seating in Woodstock

Total holiday rentals
Explore 150 holiday rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at $156 NZD per night before taxes and fees

Verified guest reviews
Over 20,170 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 80 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
150 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!
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Howe Caverns
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- Bash Bish Falls State Park
- June Farms
- Thacher State Park
- Hunter Mountain Resort
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Taconic State Park
- Mohonk Preserve
- Mohawk Mountain Ski Area
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Storm King Art Center
- Hudson Chatham Winery





