Holiday rentals in Woodstock

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Top-rated holiday rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Woodstock
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.
3–10 FebIndividual Host,
€ 131 per night
4.91 out of 5 average rating, 631 reviews
Guest favourite
Guest house in Woodstock
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
15–22 DecIndividual Host,
€ 209 per night
5.0 out of 5 average rating, 288 reviews
Guest favourite
Guest house in Mount Tremper
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.
19–26 DecIndividual Host,
€ 123 per night
4.97 out of 5 average rating, 297 reviews

Popular amenities for Woodstock holiday rentals

Stay near Woodstock's top sights

Colony153 locals recommend
Bearsville Theater195 locals recommend
Garden Cafe Woodstock234 locals recommend
Bread Alone Bakery204 locals recommend
SILVIA275 locals recommend
Levon Helm Studios98 locals recommend

Other great holiday rentals in Woodstock

Guest favourite
Cabin in Saugerties
Stunning Modern A-Frame House in the Woods
22–29 JunIndividual Host,
€ 522 per night
4.98 out of 5 average rating, 124 reviews
Guest favourite
Home in Rhinebeck
Architectural wonder in the woods
6–13 JulIndividual Host,
€ 537 per night
4.91 out of 5 average rating, 253 reviews
Superhost
Home in Mount Tremper
The Mountain Wonder - Hot tub, sauna, great views
2–9 DecIndividual Host,
€ 403 per night
4.93 out of 5 average rating, 166 reviews
Guest favourite
Guest house in Bearsville
Mt. Guardian Guest House Exquisite Mountain Views
29 Jan – 5 FebIndividual Host,
€ 189 per night
4.98 out of 5 average rating, 559 reviews
Guest favourite
Cottage in Woodstock
Woodstock Cottage In Town with large yard for pets
10–17 NovIndividual Host,
€ 227 per night
4.83 out of 5 average rating, 211 reviews
Guest favourite
Tiny home in Saugerties
Gorgeous Tiny House with Mountain View
29 Oct – 5 NovIndividual Host,
€ 121 per night
4.94 out of 5 average rating, 217 reviews
Guest favourite
Barn in Woodstock
The Woodstock Barn Studio
3–10 JunIndividual Host,
€ 118 per night
4.84 out of 5 average rating, 162 reviews
Guest favourite
Home in Woodstock
Whispering Pines: Secluded Retreat near town
7–14 FebIndividual Host,
€ 362 per night
5.0 out of 5 average rating, 121 reviews
Guest favourite
Bungalow in Woodstock
Woodstock Charmer
1–8 OctIndividual Host,
€ 208 per night
4.91 out of 5 average rating, 191 reviews
Guest favourite
Cottage in Woodstock
Hidden Pines - Downtown Woodstock by Millstream!
7–14 JunIndividual Host,
€ 227 per night
4.9 out of 5 average rating, 396 reviews
Guest favourite
Cabin in Saugerties
Pine Rock House - A modern cabin getaway
10–17 JunIndividual Host,
€ 227 per night
4.98 out of 5 average rating, 157 reviews
Guest favourite
Guest suite in Woodstock
Perfect Woodstock Location- Short Walk to Town
10–17 MayIndividual Host,
€ 174 per night
4.94 out of 5 average rating, 313 reviews

Quick stats about holiday rentals in Woodstock

Total rentals

260 properties

Rentals with dedicated workspaces

160 properties have a dedicated workspace

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

120 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

31K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Ulster County
  5. Woodstock