Cottage vacation rentals in Woodstock

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Top-rated cottage rentals in Woodstock

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Guest favorite

Cottage in Pine Plains

5 out of 5 average rating, 140 reviews

Patchin Mills Quaint Country Cottage

Welcome to your cozy cottage in the bucolic Hudson Valley. Only 90 mi. north of NYC. We welcome small dogs, under 25 lbs. with prior host approval. Sorry, NO CATS. Enjoy biking, hiking, skiing, local culture or just relaxing. 1 mile outside a charming village in farm and horse country, your cottage has a full kitchen/LR, 2 BRS (1 queen, 1 full), bathrm, washer/dryer, deck, patio & yard. Close to colleges, dining & activities. We hope that you will love this corner of the world as much as we do.

Guest favorite

Cottage in Hobart

4.8 out of 5 average rating, 173 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.

Superhost

Cottage in Gardiner

4.92 out of 5 average rating, 155 reviews

Modern 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.

Superhost

Cottage in Red Hook

4.9 out of 5 average rating, 202 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. BE SURE TO SEE OUR OTHER 2 BEDROOM COTTAGE ON THE LAKE - LILY PAD - IF YOUR DATES ARE NOT AVAILABLE.

Superhost

Cottage in Big Indian

4.91 out of 5 average rating, 117 reviews

Mountain Sky Cottage 7 - Belleayre ski 15 min away

Charming cottage overlooking the Catskill Mountains. Features a sitting area with comfy couch, picture windows with breathtaking panoramic views, a private deck, a/c, compact mini fridge, and custom-tiled bathroom with oversized shower & radiant heat. A Keurig machine, cups, lids, and assorted starter pods provided. Please bring additional pods, as we do not restock. Be prepared to walk on hilly terrain and stairs. Parking area near cottages. Belleyare skiing 15 minutes away!

Guest favorite

Cottage in Craryville

4.91 out of 5 average rating, 517 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. 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.

Guest favorite

Cottage in Catskill

4.96 out of 5 average rating, 176 reviews

Charming Cottage in the Heart of Catskill

This charming pet friendly cottage has all of the comforts of home in a fully renovated cottage. If you want to be close to it all while you are visiting the Catskills, while having privacy then this may be the place for you. We are walking distance to the Catskill Creek, Hudson River, restaurants, breweries and historic sites. 2 hours from NYC, 10 minutes from Hudson Train Station and 35 minutes from Woodstock. Hunter & Wyndham Mountain are approximately 25 minutes away.

Guest favorite

Cottage in Saugerties

4.93 out of 5 average rating, 263 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

Cottage in Walden

4.96 out of 5 average rating, 107 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

Cottage in Glen Spey

4.87 out of 5 average rating, 172 reviews

Charming cottage with Hot Tub -PET FRIENDLY

Only 1 1/2 hours from NYC. Recharge with all the beauty the Catskills have to offer. Welcome to our 100 year old cabin with updates. It is 500 square feet of pure cuteness. It exudes charm while providing comforts. 3 bedrooms and a sofa allow for lots of guests. tucked away in nature, yet just a short drive to great local finds. Please note that, although this is a cottage in a lake community, this house does not have access to the lake.

Guest favorite

Cottage in Pawling

4.98 out of 5 average rating, 106 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

Cottage in Phoenicia

4.93 out of 5 average rating, 244 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