Vacation rentals in Olivebridge

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Top-rated vacation rentals in Olivebridge

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Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 675 reviews

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.

Guest favorite

Cottage in West Shokan

4.95 out of 5 average rating, 155 reviews

Cozy Catskills Getaway on 3 Acres—Updated ‘24

You have the whole house and three acres to enjoy. The two bedrooms are upstairs, with skylights and a bright, airy feel to them. The wood burning stove is an awesome way to make things cozy. There's also a firepit and grill you're welcome to use. Guests have complete access to the home and three-acre property. The garage on the property is inaccessible by guests. We're available to contact anytime. Hike, ski, swim, bike, do yoga, or whatever comes to mind— all is possible in the Catskills. The Ashokan reservoir bike/walk path is a few miles down the road. Not far the other way is Marty's Mercantile for coffee, lunch, and basic supplies. There's plenty of parking in the driveway. Don't expect to Uber while up here. Walk, bike, or ride a horse instead. :) There's plenty of parking in the driveway.

Guest favorite

Guesthouse in Accord

4.94 out of 5 average rating, 138 reviews

Studio in Private Forest; Peace and Solitude

Set in a hemlock forest on a quiet country road, this newly redone and separate guest studio is a perfect getaway. Set on 30 private wooded acres, the property is bisected by a Class A trout stream. Guests have access to the shared pool Mon-Fri, but not Sat-Sun. The second floor studio has a queen size bed and a queen size sofa bed along with a private bathroom. There is Wifi, a television (ROKU). There is no kitchen, however, we do provide a microwave, dorm fridge and Keurig coffee machine.

Guest favorite

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 325 reviews

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.

Guest favorite

Rental unit in Stone Ridge

4.91 out of 5 average rating, 483 reviews

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 319 reviews

This New House

Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

Guest favorite

Barn in Stone Ridge

4.93 out of 5 average rating, 277 reviews

Hudson Valley Botanical Garden Rental

Located in Upstate New York on the edge of our Botanical Garden in the Lower Hudson Valley the "Barnette" is for nature lovers. This newly built repurposed barn is perfect for relaxing, exploring nature, and getting away from it all. Nearby are lots of hiking, rail trails, and farms. We are within driving distance of the Mohonk Mountain House, Minnewaska, Catskill Mountains, and a 2 hour drive from Manhattan. For winter enthusiasts there’s places to snowshoe, ski, and hike 20-60 minutes away.

Guest favorite

Home in Olivebridge

5 out of 5 average rating, 113 reviews

Olive Outpost: Catskills 3BR House on Private Road

Welcome to the Olive Outpost in The Catskills! (@oliveoutpost) Our light-filled, 1,600 SF, 3-bed, 2-bath house is on 32 acres off a private road and ideal for a small group (6 or under). We're close to the towns of High Falls, Stone Ridge & Accord (15 mins), Woodstock, Phoenicia (25 mins) & Kingston (30 mins). NOTE: There is a guest cabin on the property where the owners may be staying (or available for additional capacity) Photos courtesy of @nicoschinco Town of Olive STR Reg #: STR-22-6

Guest favorite

Guesthouse in Woodstock

4.96 out of 5 average rating, 327 reviews

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace

Snuggle by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical home has a private deck w/bbq, a garden with a hammock and fire pit. A full size Murphy bed with a full kitchen (except for an oven). You will have access to the entire guest house. A short drive to the beautiful, eclectic, funky town of Woodstock. Art & culture, restaurants, hiking & biking all nearby. Electric heat, ceiling fan, a standing ac unit and single person shower.

Guest favorite

Guesthouse in Olivebridge

4.93 out of 5 average rating, 120 reviews

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old former Boarding House which housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed/child friendly!). Near Kingston, Woodstock and Stone Ridge.

Guest favorite

Cabin in Kerhonkson

4.92 out of 5 average rating, 431 reviews

Home Alone Woods

Small and charming cabin in a quiet place surrounded by woods and nature with the hiking trails half a mile away. There is an easy access to Hunter Mountain, Minnewaska State Park, and Shawangunks. This is a perfect getaway for nature and outdoor enthusiasts, bikers, hikers, climbers, and skiers or people who look for peace and tranquility in the woods.The kitchen is equipped with cooking essentials such as pots, pans, and utensils. WE DO NOT GUARANTEE THAT THE HOT TUB WILL BE AVAILABLE.

Guest favorite

Chalet in Olivebridge

4.99 out of 5 average rating, 145 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Secluded log home on 5 acres, beautifully situated at the top of a no outlet road on a mountainside in the Catskills. The home has 4 bedrooms + 3.5 baths, with the 4th bedroom being a finished basement that has built-in full size bunk beds. There is also a sunroom, screened porch, pool, hot tub, and a treehouse that resembles a floating pirate ship 30 feet up in the trees, oh, and now a Projector TV in the basement! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500