Cottage vacation rentals in Woodstock

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Top-rated cottage rentals in Woodstock

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Guest favorite

A stone path winds through a lush, green yard, bordered by trees and wooden fence posts. The inviting entrance of the cottage is visible, surrounded by vibrant flora, creating a serene outdoor setting that emphasizes the property’s natural beauty.

Cottage in Craryville

4.91 out of 5 average rating, 525 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit and laundry facilities. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking

Superhost

A wooden chair faces a gently flowing stream, surrounded by tall trees in a tranquil setting. Sunlight filters through the branches, creating a serene ambiance by the water's edge.

Cottage in Hobart

4.81 out of 5 average rating, 187 reviews

🌟Riverfront Cottage W/2 Bedrooms Catskills 🌟

Enjoy our renovated farm house. Relax at this peaceful riverside cottage. Listen to the passing stream from every room in the house. Cottage features a Hammock, backyard fire pit, private swimming hole, Trout fishing, voice activated speakers throug, full kitchen, two bedrooms with queen's and laundry.Surrounded by 200 acres of state land you're free to explore. Cottage is located in Hobart NY, the bookstore capitol of NY. 25 min to Plattekill Mountain ski resort, Belleayre Mountain Ski Center.

Guest favorite

The exterior of a modern A-frame cottage is nestled among tall trees, featuring dark wood siding and large windows. A wooden deck extends in front of the entrance, with a few steps leading up. Stacked logs and stones are visible in the foreground.

Cottage in Kerhonkson

4.87 out of 5 average rating, 222 reviews

Beautiful stream side cottage in the woods

Stunning fully renovated 1970 partial A frame cottage in the woods! Set privately on four acres with a stream and meandering stone walls, the cottage is modern yet rustic, with a mid century decor. Main floor has living room with beautiful floor to ceiling stone fireplace (gas operated), kitchen, bathroom, and an office with a desk and twin bed. Second floor has master bedroom with queen size bed and a separate loft area with desk. Great place to relax in nature - a perfect couple's getaway!

Superhost

A cozy living area features a stone fireplace framed by vintage skis. Natural light streams through two windows, illuminating a plush sofa and an armchair. A glass coffee table rests on a colorful area rug, complemented by greenery in a pot and minimalist artwork on the walls.

Cottage in Gardiner

4.9 out of 5 average rating, 161 reviews

Little Cottage Under the Ridge

Visit the cottage for an upscale retreat in the rock climbing epicenter of New York’s famous Shawangunk ridge. our mountain top paradise sits on a dead end road amongst untouched nature, only minutes to town, with a small chef’s kitchen, breakfast bar, and brand new everything. As the last property before Minnewaska’s protected preserve land, the cottage offers unmatched peace and quiet. Enjoy a private campfire beneath mature maple & oak trees that decorate our secluded five acre property.

Guest favorite

The inviting exterior of the Esopus Cottage showcases a quaint white facade with a green roof. A front porch features two metal chairs and a small table, surrounded by lush greenery and well-maintained bushes, creating a tranquil setting. Tall trees frame the property under a partly cloudy sky.

Cottage in Phoenicia

4.91 out of 5 average rating, 631 reviews

Romantic Getaway: Lovingly Restored Esopus Cottage

The Esopus Cottage is perfect for relaxation, working remotely and serves as a hub for experiencing the majestic Catskills. Featured in Curbed NY, a travel magazine, as “The Best Vacation Rentals in the Hudson Valley," the Esopus Cottage has over 700 five-star reviews. Catskill Getaways has over 2,100 five-star reviews. As Airbnb Superhosts for 11+ years, we are committed to stellar customer service and making your vacation a memorable and restorative experience. License # 2023-STR-055P

Guest favorite

A spacious studio features a renovated ceiling with wooden beams and skylights. Large glass doors provide access to the outdoor area. Colorful textiles embellish the seating area, while a dining table is set with place settings. A kitchenette is visible in the background.

Cottage in Phoenicia

4.9 out of 5 average rating, 879 reviews

Romantic hot tub cottage. Breweries/hiking nearby

Your perfect romantic country retreat with private courtyard, steamy outdoor hot tub and fire pit offering the feeling of complete seclusion yet only a couple of minutes walk from fabulous Main Street speciality stores and restaurants. 2 minutes to Woodstock Brewing and Phoenicia Diner. Bike the rails with Rail Explorers just around the corner or hike the bucolic Tanbark Trail from the park behind our property or the famous Ashokan Rail Trail from Boiceville ( 8 minutes drive)

Guest favorite

A screened-in dining shed features a long wooden table set for a meal, with plates and condiments arranged neatly. The floor is covered with white gravel, and soft, ambient lighting is hung overhead, creating a cozy space for al fresco dining.

Cottage in Saugerties

4.93 out of 5 average rating, 289 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.)

Guest favorite

A well-maintained cottage is framed by lush green grass and tall trees. A neat path leads to the front door, which is accented by a vibrant red door. The cottage overlooks a serene lake, enhancing its inviting exterior.

Cottage in Walden

4.96 out of 5 average rating, 108 reviews

Cute, Cozy, Lakefront cottage

Cute, cozy lakefront cottage on private lake. Deck with an unobstructed view of the lake. Stunning sunrises, pinewood floors in bedroom/living room/kitchen. Queen size bed in bedroom. Situated on the same lot as owner occupied main house. Quiet, residential area. Near wineries, breweries, hiking. WIFI. No TV. Unfortunately, due to severe pet allergies I am unable to host any kind of animals including emotional support and service dogs and cats of any kind.

Guest favorite

The restored a-frame stone cottage is nestled among trees, featuring a wooden deck and stone steps leading to the entrance. A propane grill is positioned on the deck, with a tranquil wooded backdrop showcasing the colors of nature.

Cottage in Pawling

4.98 out of 5 average rating, 120 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Guest favorite

A snowy pathway leads from the cottage, flanked by trees on either side. Gentle, warm light from hanging bulbs illuminates the covered deck area, while a tranquil creek is visible in the background, with a soft blanket of snow covering the ground.

Cottage in Phoenicia

4.94 out of 5 average rating, 262 reviews

Charming creekside cottage in Phoenicia

Come relax in one of the prettiest places in the Catskills. Enjoy views of the Stony Clove, while sipping coffee on the wrap-around deck. The location is private and quiet, yet convenient to all the region's many attractions - hiking, skiing, antiquing, eating. When you are done exploring, enjoy a dip in one of the largest, deepest swimming holes in the area. Perfect for small families and couples. License Number: 2022-STR-AO-081

Superhost

A small outdoor seating area features two metal chairs and a round table, surrounded by lush greenery. The view looks out onto a calm lake, partially obscured by foliage, creating a serene and private atmosphere.

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you.

Top guest favorite

Two red Adirondack chairs are positioned on a rocky outcrop beside a gently flowing stream. Surrounding areas are adorned with fallen leaves and tall trees, creating a natural setting with the calming sounds of water and nature.

Cottage in Woodstock

4.95 out of 5 average rating, 292 reviews

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. Enjoy!