Vacation rentals in Olive

4.96 out of 5 average rating, 173 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, 120 reviews

Guesthouse 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, 147 reviews

Guesthouse in Accord

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.

4.99 out of 5 average rating, 160 reviews

Cabin in Rochester

The Black Dymond A Private Streamside Cabin

A 2.5 hour drive from NYC to a serene, private, woodland, streamside home. This cabin sits on the very edge of the Catskill Mountains. It's cozy, modern, and minimalistic with a touch of rustic elegance. All new appliances with all the cooking necessities, a comfortable bed with large screen smart tv, excellent wifi service, a romantic gas-powered fireplace and the most private back deck away from the world to get lost for a weekend in the beauty of the woods.*Now offering mid-week price deals!

4.92 out of 5 average rating, 532 reviews

Apartment in Stone Ridge

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.

4.93 out of 5 average rating, 294 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

4.94 out of 5 average rating, 135 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, 124 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.

Guesthouse 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.

4.92 out of 5 average rating, 177 reviews

Cottage in West Shokan

Relaxing Cottage in the Catskill Mountains

1000 sq ft. cottage located on a 7 acre partially wooded property in the Catskills. Two bedrooms (one queen, one full), one bath, open floor plan with vaulted ceilings and sliding glass doors opening to a deck in the back yard. Cook and eat on the deck with both gas and charcoal grills, plus large dining table with umbrella. Fire pit outside and wood burning stove inside for extra warmth and ambience. Dogs considered, just ask.

Guesthouse in Mount Tremper

4.92 out of 5 average rating, 356 reviews

Cozy Catskill Cottage Perfect Getaway for Two

NEWLY RENOVATED, COZY, CLEAN, PRIVATE AND SECURE Cottage in scenic and peaceful locale. Convenient and easy to find near the town of Phonecia, NY. 100 PACES to the ESOPUS RIVER and its trout fishing, trail heads and scenic hikes less than a mile away. Close to numerous sophisticated dining and shopping options. Less than 30 minutes to BelleAyre and Hunter Summer Happenings. Perfect for couples who need a weekend country getaway.

4.94 out of 5 average rating, 510 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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Olive vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Olive

4.94 out of 5 average rating, 79 reviews

Cottage in Kerhonkson

Mountain Retreat on 17 Private Acres - Kerhonkson

JeremyRating, 5 stars1 week ago

My boys and I had a wonderful Father's Day weekend at Talitha's charming mountain cottage. It had everything we needed and when I had questions, Talitha responded within minutes. And all around great experience.

5 out of 5 average rating, 17 reviews

Olive Outpost: Catskills 1BR Meadow House For 2

SarahRating, 5 stars4 weeks 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.

5 out of 5 average rating, 9 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!

4.96 out of 5 average rating, 24 reviews

Olive Star Cottage & Garden

EmilyRating, 5 stars2 months ago

The cottage was modern and clean and provided all the necessities of home. The beds were very comfortable, the kitchen had all the basic staples, and the dining table had a perfect view of the backyard and surrounding wildlife (deer every morning). The location of the cottage is close enough to Woodstock village and Ashoken reservoir for daily activities.

5 out of 5 average rating, 54 reviews

Home in Kerhonkson

Modern Cabin on 7 Acres in Catskill forest w/ Pond

GretchenRating, 5 stars2 weeks ago

Great place to stay in the Catskills if you want something peaceful in the woods. It was a great price for how clean, quiet and aesthetically pleasing this place was. While it was off the beaten path, it was a short drive to many of the cool places in the area and the hosts give a great book of recommendations that was very helpful. Would stay here again!

4.98 out of 5 average rating, 99 reviews

Camper/RV in Boiceville

Airstream by the Stream (Ashokan Reservoir)

LiamRating, 5 stars5 days ago

We couldn’t have found a more perfect place for a relaxing + private getaway. We absolutely fell in love with the beauty and peacefulness of the area. This was our first trip to the Catskills and hopefully not our last. Thanks for sharing such a cozy space!

4.96 out of 5 average rating, 26 reviews

Cottage in West Shokan

Ashokan ArtHaus, Private Hot Tub, Wags Welcome!

OliviaRating, 5 stars1 month ago

The cottage is an absolute gem! It is in a beautiful location and the space is nurturing and comfortable. The star room and outdoor area add a special element as well. I look forward to staying again in the future.