Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Top guest favorite
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
4.95 out of 5 average rating, 38 reviews

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!!

Guest favorite
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
4.86 out of 5 average rating, 95 reviews

'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.

Guest favorite
A rustic cabin is nestled among tall trees, with a welcoming front porch featuring wooden steps and a seating area. An American flag gently flutters at the entrance, while two bright windows allow light to enter, framing the structure in a natural, wooded setting.
Cabin in Camden
4.85 out of 5 average rating, 46 reviews

Empeyville Escape Peaceful Wooded Camp

Enjoy a peaceful, relaxing getaway at this rustic, cozy, 2 bedroom cabin situated on 14 beautiful acres of wooded land. If you love nature, four wheeling, fishing, snowmobiling, C41 trail, hunting or just kicking back by a campfire, listening to the quiet and star gazing, this is the place to do all that, and more. Empeyville Escape is centrally located to the snowmobile and ATV trails, Tug Hill and the Adirondacks, also some of the finest fishing in upstate NY. Family-friendly and pet friendly.

Guest favorite
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.
Cabin in Town of Redfield
5.0 out of 5 average rating, 20 reviews

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.

Guest favorite
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
4.75 out of 5 average rating, 143 reviews

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.

Top guest favorite
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.
Cabin in Town of Redfield
4.98 out of 5 average rating, 57 reviews

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!

Top guest favorite
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
4.97 out of 5 average rating, 33 reviews

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).

Superhost
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
4.78 out of 5 average rating, 49 reviews

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!!!

Guest favorite
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
4.85 out of 5 average rating, 202 reviews

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.

Superhost
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
4.9 out of 5 average rating, 10 reviews

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.

Superhost
A log cabin-style home is presented with a metal roof and large windows. The front porch is accessible with wooden railings, and a grassy area is visible alongside gravel leading to the driveway. Surrounding trees provide a natural backdrop.
Home in Town of Redfield
4.95 out of 5 average rating, 133 reviews

Lake Effect Lodge | Tug Hill | Hot Tub | Pets OK!

Welcome to our custom-designed Tug Hill home, perfect for a vacation getaway. - 3 bedrooms with a log cabin feel - Approximately 1100 sqft of living space - Full bathroom with in-floor radiant heat - Large kitchen with stainless appliances - Hi Speed Wi/Fi internet - 50' wide screen TV and DVD player - Large covered porch with gas grill - Wood stove and propane heater - Large driveway for trailers and vehicles

Guest favorite
The living area features warm knotty pine walls and a high ceiling, filled with natural light from large windows. A sectional sofa is positioned in front of a wall-mounted TV. A dining table with chairs complements the space, surrounded by sleek wooden flooring.
Cabin in Osceola
4.92 out of 5 average rating, 13 reviews

The Timber Knot

"Discover 'The Timber Knot,' a cozy year-round cabin in the Tug Hill Region. Enjoy knotty pine interiors, a 65" TV, and modern amenities. Step outside to a deck overlooking 5 acres and the snowmobile and ATV trails. Nearby, find Cedar Pines restaurant and gas, or a Short drive to Salmon River Reservoir for fishing. Kids can play in Prince Brook Creek just a short walk away. Your ideal getaway awaits!"

Popular amenities for Osceola vacation rentals