Holiday rentals in Olivebridge

4.96 out of 5 average rating, 172 reviews

Cottage in West Shokan

Cozy Catskills Getaway on 3 Acres near Woodstock

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.

4.99 out of 5 average rating, 115 reviews

Guest house in Olive

The Lily Cottage Guesthouse

Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

4.93 out of 5 average rating, 293 reviews

Barn in Stone Ridge

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 suite in West Shokan

4.95 out of 5 average rating, 130 reviews

Stylish and Cozy Mountain Retreat

Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

4.97 out of 5 average rating, 121 reviews

Home in Shokan

West Wing - a unique private space w/deck

This unique studio space with private entrance is a recent addition to our charming home, located on a quiet private road in the village of Shokan. Situated within minutes of the Ashokan Rail Trail, this bike and walking trail offers dramatic vistas of the Ashokan Reservoir. Woodstock & Phoencia with their stores, galleries and restaurants are only 15 minute drives . Local recreation includes hiking trails, kayaking and for those looking for relaxation there are renowned spas.

4.9 out of 5 average rating, 134 reviews

Guest suite in New Paltz

Newly built apartment steps from Mohonk preserve.

Nestled amongst the trees below Bonticou Crag this is a great base camp for climbing, hiking and biking. Five minutes from New Paltz; I do recommend having a car to access the area. Shared yard and fire pit right outside. My family and I live in the main part of the house. The outside area and house are still under construction, I’m working on it but its not put together yet. The apartment and inside area are clean and newly built with their own mini split and air circulation.

Guest house in Olivebridge

4.94 out of 5 average rating, 147 reviews

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old farmhouse which originally 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). Near Kingston, Woodstock and Stone Ridge.

4.97 out of 5 average rating, 232 reviews

Cabin in Stone Ridge

Modern Cabin Getaway: Idyllic, Secluded, Serene

Escape to our charming log cabin, nestled on a serene 6-acre property surrounded by the soothing sounds of nature and scenic beauty. Though perfectly private, the cabin is conveniently located near markets, shops, restaurants, and just a short distance to the heart of town. An ideal escape Less than 2hrs from NYC. Hiking, nature trails, swimming holes, skiing, local farms, wineries, reservoirs, waterfalls, historic sites, all await you. IG:@griffithhousecabin

4.89 out of 5 average rating, 576 reviews

Flat in Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge

First floor apartment in historic colonial house in the middle of Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original pieces of art. It has a fireplace stove and a wood fired sauna in the backyard. Full kitchen is equipped with everything guests need to prepare a great meal. It is perfect for all seasons. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

4.99 out of 5 average rating, 309 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

4.94 out of 5 average rating, 508 reviews

Cabin in Olivebridge

Cozy Catskill Cabin on Acorn Hill

Enjoy a rustic respite from the city in this cozy cabin on 3.5 acres near the beautiful Ashokan reservoir and Catskill Park. Perfect for a relaxing weekend and as a hub for skiing and hiking. Cabin includes 1 bedroom and one bath, full kitchen, and living room with piano. This is a perfect get-away to relieve the stress of the city. Full amenity details are available in the listing. Town of Olive Registration # STR-22-19

4.96 out of 5 average rating, 121 reviews

Barn in West Shokan

Renovated Barn w/Private Deck & Patio

Hidden away on a 4 acre lot at the end of a dead end road, this renovated barn is the perfect cozy getaway. Complete with king size, memory foam mattress, oversized bath, private deck w/ Weber Grill, & lower patio w/ Modern Adirondack Chairs, and Cowboy Cauldron fire pit right on the edge our little creek…it's the epitome of relaxation. ------------------- Reg #STR-22-7

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4.93 out of 5 average rating, 76 reviews

Cottage in Kerhonkson

Mountain Retreat on 17 Private Acres - Kerhonkson

DavidRating, 5 stars1 week ago

We had a brilliant stay here with our dogs over the weekend. Superb location close by some beautiful hikes and we also just enjoyed chilling at the house. Would definitely stay there again!

5 out of 5 average rating, 78 reviews

Olive Woods House - Catskills Mountain Views

PriscillaRating, 5 stars1 month ago

We loved our stay at Olive Wood. I think the pictures didn’t do it justice! The house was full of charm and character with a design blend of boho and mid century modern. It was our perfect vibe. We especially enjoyed the outdoor space with our puppies and the screened in area. Our hosts were incredibly responsive and gave wonderful recommendations for local restaurants, coffee spots etc … We had a great weekend and hope to return.

5 out of 5 average rating, 17 reviews

Olive Outpost: Catskills 1BR Meadow House For 2

SarahRating, 5 stars1 week ago

Michael and Nick's Meadow House was one of the absolute best Airbnb stays we have ever enjoyed! It's truly a dream home with everything you will need for your stay. Standout details included a comfy bed, a dream kitchen with everything you'll need to cook your meals, spa-like bathroom, and a cozy fireplace that you can light with the push of a button. The views from every room are stunning and peaceful. We enjoyed coffee and birdsong on the porch every morning. We saw lots of birds, deer, chipmunks and woodchucks. And it's a short drive to lots of trails and charming towns. We had a welcome note and snacks waiting for us on our arrival. Michael was so friendly, responsive, and gave lots of fantastic recommendations. He was also so helpful with all our questions and a work emergency that came up for me. We were dreaming of returning for a longer stay before we had even left.

4.94 out of 5 average rating, 338 reviews

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

CodyRating, 5 stars1 month ago

No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

4.98 out of 5 average rating, 63 reviews

Country Getaway with Mountain View

CatherineRating, 5 stars1 month ago

This was the perfect vacation house in the woods for our family. My two young children loved all of the toys available. I quickly realized I did not have to even open the bag of books and toys we brought with us because there was more than enough here! Being in the middle of the woods was exactly what we were looking for. The house was well stocked with towels and all necessary cooking supplies. I would suggest a couple of extra blankets for cooler weather, as the bedroom downstairs was quite cold when we arrived. Otherwise, we had an excellent stay and we would definitely come back.

4.97 out of 5 average rating, 155 reviews

Home in Kerhonkson

ENTER HOME - Minimalistic style warm & inviting

MeirRating, 5 stars1 week ago

Monika's home was one of the best airbnbs we have ever stayed in. The design, style, and quality is something unparalleled in other airbnbs, it has a cohesive, elevated design throughout the entire home. It has everything you could possible need and is so thoughtful in every way. The backyard is huge and is perfect for a family to spend time together. We went on a great hike to a waterfall (which is within walking distance). Location is amazing as it's a close drive to Minnewaska. The location in Kerhonkson is in a nice secluded area. If you're looking for the perfect place to stay in the area this is it!

5 out of 5 average rating, 8 reviews

The Earthmover Inn

SukiRating, 5 stars5 months ago

Staying at the Earthmover Inn was the best decision we made this holiday! The house was impeccably clean and cozy, and Roger and Ruth left lots of great treats, like small chocolates and coffee and tea. We had a blast playing Scrabble by the fire, and the whole stay was wonderful. Roger and Ruth are attentive and kind communicators, and you can tell they care a lot about the comfort of the folks staying here. The BNB is within 10 minutes of Stone Ridge, and only a few minutes away from Tetta's and the Country Inn, for closer options for groceries and food. I grew up in the neighborhood, and staying here while visiting family for the holidays made me feel right at home!