Cottage vacation rentals in Woodstock

Contemporary Guesthouse with Heated Pool

Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

Value · Family · Skiing

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".

Value · Family · Parking

Woodstock Dog Friendly Cozy Cottage in Town + 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!

Value · Location · Quiet

Woodstock Mountain Cottage w/ Swimming Pool

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 your tv needs! Located just 3 mins to the center of Woodstock. Swim in the pool, hike a trail, enjoy nature, grill or relax in the hammock. Pool is shared only with hosts & very private. No guests of guests allowed & no parties.

Value · Location · Amenities

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.

Family · Value · Amenities

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek.

Family · Location · Cleanliness

Mountain views, mid-century style! 1 mile to town.

Spacious, stylish, light filled studio guesthouse with gorgeous mountain views on 4 acre estate. Wake up to a view of the Catskills, seen through an expanse of sliding glass doors. Eat breakfast on the balcony, or relax on the couch while watching the sun go down. Inside: luxuriously comfortable, eco-friendly queen mattress, 50" smartTV, full kitchen, full bath. Outside: picnic table, hammock, cascading brook, land to explore. Good wifi inside/outside. (Woodstock STR permit #23H-279).

Location · Value · Kitchen

Woodstock Streamside Cottage

Our streamside cottage is located on a five acre property under a mile to the center of Woodstock. The Sawkill Stream is your backyard with plenty of beautiful trees and meadows your front yard. Quiet sounds of the stream and nature surround you. Central heat and central a/c keeps you comfortable year round. Newly renovated. Please read our reviews and see how you'll feel. About 1.5 miles from the Ramble concert venue and 2.5 miles from the Bearsville Theater area. Enjoy!

Family · Location · Condition

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.

Value · Family · Breakfast

Mirror Moon Cottage (waterfront)

Mirror Moon cottage is a newly renovated, original 1960's cottage in the heart of a historic arts and music community. The property is waterfront, overlooking the Saw Kill, with tranquil views & sounds. Imagine falling asleep to the sounds of the river on our hammock. Only an 8 min bike ride, or 4 min drive to the center of Woodstock town. It's subtly tucked into the woods, just outside of town. Perfect for a friends or couples getaway! Make yourself at home!

Value · Family · Pets

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.)

Value · Location · View

Stunning Woodstock 1 BR Hideaway

Find complete tranquility 5 minutes from Woodstock's bustling Village Green. This sun filled space is situated on a lovely 15-acre owner-occupied property with a private porch and bluestone patio which overlook the forest, seasonal stream and falls. Your only neighbor is the owner, a local painter and sculptor, who lives across the stream.

Location · Value · Pets