Vacation rentals in Osceola

4.95 out of 5 average rating, 39 reviews

A scenic view of a lodge surrounded by lush greenery and vibrant wildflowers. The house, featuring a white exterior, is positioned on a hillside, with trees in the background and a gentle slope leading down to a pond.

Home in Town of Redfield

Fireball's Lodge at Redfield NY Great Outdoor Fun

Our Lodge sleeps up to 35 people with 3 large living rooms. Want to host a Wedding, Reunion, Family Get Away, or Corporate Event,This home can handle it! Great for Chefs who want to try out the Commercial Viking Stove,Sportsman and hiking.We have hundreds of acres.including our pond with Covered Bridge. Mountain biking, Cross Country Skiing Snowmobiling and ATVs and our Boat Swing Set for Kids Boating and Swimming in reservoir. Salmon fishing and Salmon river falls close by. Come join the Fun!!

4.86 out of 5 average rating, 95 reviews

A newly built chalet stands amidst a blanket of snow, surrounded by tall, leafless trees. The structure features a sloped roof and large windows, which reflect the serene winter landscape. A clear path winds through the snow towards the entrance.

Home in Camden

'Into the Woods'-- Stunning New Tug Hill Retreat

This stunning, chalet is set on a ridge in 17 beautiful, private, wooded acres. Relax with friends & family on the front porch while taking in the summer & fall foliage. Come with your ATVs and snowmobiles. We have plenty of parking for your trailers. Enjoy an evening around the fire pit gazing at the Milky Way. Explore the natural beauty of nearby falls, & state forests, or hike the property & wade in the creek. Rainy day? Cozy up in the great room for movies or head upstairs to the game room.

Cabin in Town of Redfield

A wooden porch extends along the front of the cabin, featuring sturdy railings and steps leading to the entrance. Natural wood tones dominate the structure, with a mix of large windows and an exterior light fixture. Gravel surrounds the base, enhancing the rustic appeal.

Camp DeLong

Camp DeLong is ideal for families and friends who love the outdoors, seek outside adventure or just want to take in the Upstate NY scenery. All season located in the foothills of Tug Hill. Peaceful new construction cabin retreat sits on 7 acres less than a mile from the Salmon River Reservoir, directly off of snowmobile/ATV/UTV trails, and surrounded by Forever Wild NYS hunting land with panoramic views from the covered porch. Smart TV, high speed wifi, plenty of parking for trucks/trailers.

5.0 out of 5 average rating, 20 reviews

4.75 out of 5 average rating, 143 reviews

A spacious lodge is depicted under a clear blue sky, featuring two snowmobiles parked in the snowy foreground. The building includes multiple windows and a welcoming porch, suggesting access to outdoor activities in a winter landscape.

Cabin in West Leyden

Winter Wonderland Outdoor Get Away

Our Lodge is close to family-friendly activities You’ll love the lodge because of the location and the views. Our lodge is good for couples, families (with kids), and big groups. Snowmobiling trails and quad runner trails run for hundreds of miles. The woodsman festival in Booneville in August, fishing almost anywhere with the huge salmon run on the Salmon River and tributaries in October, November and Steel Head fishing in Nov, Dec, Jan, Feb and March and beginning of April being the best.

Cabin in Town of Redfield

The exterior of the cabin is showcased with a charming blue facade and a triangular roof. A wooden deck features a propane grill and a dining table with four chairs, providing a cozy space for outdoor gatherings surrounded by nature.

Little John Tiny Cabin

Welcome to the Little John Tiny Cabin! This tiny cabin is located on Little John Drive, a plowed road AND part of the main snowmobile trail system on Tug Hill. The Tug Hill fun doesn’t stop when the snow melts. The ATV trails are plentiful, as well as the hiking, hunting, fishing and swimming opportunities! The Little John Tiny Cabin makes the perfect hub for your adventure. With WiFi, coffee, and linens included, all you’ll need to bring is some fresh clothes and a bite to eat!

4.98 out of 5 average rating, 58 reviews

4.95 out of 5 average rating, 119 reviews

Home in Lyons Falls

Secluded 3 Bedroom cabin w/4+ private acres

This secluded three-bedroom home, situated right on the atv trail system. Plenty of parking space. Over four acres of private land with an enormous lawn that’s all yours to enjoy! With so many things to do in the area, there is something for everyone! The Adirondack Park border is just a miles up the road. There are many hiking trails and horse riding trails nearby as well. Rivers and Lakes to kayak, canoe, fish or swim in are in abundance here. You can also just relax!

4.97 out of 5 average rating, 33 reviews

A single-story home features a combination of wood and stone exteriors beneath a metal roof. The front is accentuated by a small porch, and a flag is displayed on the side. The surrounding landscape includes lush green trees and a spacious lawn.

Home in Constableville

L ‘n R Rider’s Retreat

Enjoy this riders paradise. We would love for you to enjoy our home away from home. This two bedroom, one bath home is directly on the atv trails and an easy ride to the snowmobile trails. Close to the ADK state park, fishing, hiking and both downhill and cross country skiing. Four beds and access to two single cots (upon request) makes it a great retreat for you and your riding group. Plenty of parking for your trailer and machines (garage not available for guest use).

4.78 out of 5 average rating, 49 reviews

The exterior of a two-story home features a combination of red clapboard and wooden siding. A green lawn surrounds the house, with a gravel driveway visible. Steps lead to the front door, which is framed by a small porch area. A vehicle can be seen parked nearby.

Home in Osceola

Osceola Sportsman Lodge

Two bedroom 1st floor home, Bdrm 1- 1 Queen bed, 1 double bed, Bdrm 2- 1 Full bed and 1 queen bed, Full Kitchen, 1.5 Baths, laundry, porch and outdoor space with lots of parking for multiple vehicles and trailers located in the Tug Hill right across the street from the Osceola Hotel( Bar/restaurant)and Osceola Outpost(breakfast and lunch). The snowmobile trai is right out the front door and short trip to ATV trails. Close to The Osceola Ski Resort and Salmon river!!!

4.85 out of 5 average rating, 202 reviews

The cabin features a rustic wooden exterior, framed by lush trees and well-maintained grass. A gravel driveway leads up to the entrance, where a vehicle is parked. The two-story structure has large windows and a front door, inviting exploration of the surroundings.

Cabin in Taberg

Knotting Pine Cabin

Knotting Pine Cabin is very spacious and can sleep 9 people. If you are looking for a great get away with friends and family you will love this cabin. Guests can enjoy walking the paths in the forest adjacent to the cabin, a game of horse shoes, canoe available for guests to take to the local ponds and reservoir. Enjoy camp fires and making s'mores at night. We are located on the Tug Hill Plateau with access from the cabin to the NYS snowmobile trail system.

4.9 out of 5 average rating, 10 reviews

The exterior of a cozy house is framed by lush green grass and shade trees. A red door adds a pop of color, while an American flag flutters gently in the breeze. The house features a combination of grey siding and a red accent wall, inviting visitors to explore.

Home in Camden

Welcome to Hawk Haven!

Come in! Kick off your shoes and relax! Hawk Haven is a cozy place to enjoy with family and friends, or a quiet retreat, if solitude is what you're looking for. We are located right behind Osceola Hotel. We kindly ask that you not bring pets with you for your stay. Close to fishing, atving, snowmobiling, hiking, cross-country skiing, and anything outdoors you can think of! We're out of the way, yet close to all of your necessities.

5.0 out of 5 average rating, 8 reviews

Home in Altmar

Cozy Home in the Woods

Relax with friends and/or family at this peaceful home in Altmar, NY! This home is in close proximity to the Salmon River and Reservoir. Great spot for local hiking, fishing and snowmobiling season. Two guest bedrooms with three beds and bathroom. Additional primary bedroom with one bed and private bathroom. Open living, dining and kitchen space. Grill and fire-pit available for use. Plenty of privacy and parking.