Holiday houses in Osceola

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Top-rated holiday rentals in Osceola

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Guest favourite
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
4.85 out of 5 average rating, 88 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.

Top Guest favourite
A rustic cabin exterior is shown, featuring a green metal roof and wooden siding. Two yellow rocking chairs are positioned on the porch, along with a small table. A BBQ grill is visible to the right, surrounded by lush greenery from the surrounding trees.
Cabin in Parish
4.96 out of 5 average rating, 249 reviews

Woodland Retreat, the perfect getaway from it all.

Private retreat on 45 acres, 5 miles from major highway. Salmon river 20 mins drive, snowmobile trails across the road. Private cozy cabin, queen size bed and futon. This is all one area with a private bathroom. Bathroom has full size shower, kitchen area a microwave, fridge, coffee maker and inside grill. Tea, coffee, water provided. BBQ on the front porch. Woodland trails, wildlife and privacy. No smoking or vaping in the cabin. Perfect for retreats or just being able to relax and breathe

Top Guest favourite
A studio apartment features a spacious bed dressed in light bedding with patterned accents. Soft curtains frame the windows, allowing natural light to illuminate the room. A cozy seating area includes a gray sofa, while a desk with a chair is positioned nearby.
Apartment in Lowville
4.98 out of 5 average rating, 179 reviews

Old Jail at St. Drogo's

The Old Lewis County Jail at St. Drogo's house is part of a revitalization and repurposing of the county's old jail. In addition to this residence, St. Drogo's house has a coffee roastery / coffee bar as well as an artisanal bakery located on the first floor. Wake up to the smell of freshly baking croissants and espresso! Lowville is in the geographical center of Lewis County. We're a stone's throw from the Adirondacks, the Black River and the Tug Hill. Come Enjoy Lewis County all four seasons!

Top Guest favourite
An A-frame cottage is framed by lush greenery, featuring a dark wood exterior with a centrally located white door. An overhanging carport provides coverage for vehicles, while hanging planters add a touch of color to the entrance. A pathway leads to the cozy front yard.
Cottage in Sandy Creek
4.96 out of 5 average rating, 325 reviews

🌙 Olde Salem A-Frame Cottage 🔮 near Lake Ontario

You are steps away from witnessing the greatest sunsets along North Sandy Pond (across from Lake Ontario) when you stay at our relaxing, unique, and cozy A-frame - inspired by all things magical and earthy. Sit by the backyard fire, sip coffee by the electric fireplace, read a book in the bedroom nook, play board games, dance in the kitchen, and enjoy four seasons of nearby activities such as fishing, kayaking, boating, jet skiing, hiking, swimming, ice fishing, snowmobiling, and snowshoeing.

Guest favourite
A centered wood stove is flanked by two windows, offering a warm focal point in the room. A mounted television is positioned above the stove, while a small side table stands nearby. Rich wood paneling and a patterned rug add texture to the floor.
Cabin in Redfield
5 out of 5 average rating, 13 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.

Top Guest favourite
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 Redfield
4.97 out of 5 average rating, 30 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!

Guest favourite
Two red snowmobiles are parked on a snowy area in front of a home. The house features a covered porch with brown wooden railings and multiple seating options visible. The clear blue sky complements the winter landscape.
Cabin in Williamstown
4.88 out of 5 average rating, 25 reviews

Redfield Retreat

Enjoy the summer hike to the Salmon River Waterfall 18 minute drive. Ride your snowmobile from the house, the trail is half mile away on Ryan Road. Ride your ATV, the Oswego County ATV Trails or Osceola ATV Club Trails right from the house. Bring your boat and take it out on the Salmon River Reservoir, perfect for swimming, fishing, kayaking, and only a 6 minute drive from the house with a nice boat launch and parking. About 20 minutes drive from the Salmon River.

Top Guest favourite
A rustic cabin is illuminated by string lights, inviting a cozy atmosphere. Stone steps lead to a sheltered porch, where seating is accessible. Surrounding trees enhance the natural ambiance, and gravel paths create a quaint outdoor setting shaded by greenery.
Cabin in Lorraine
4.99 out of 5 average rating, 509 reviews

Bear Hill One Room Cabin with Hot Tub

Unplug during your trip in the middle of the woods, tiny rustic one room cabin with hot tub sits in Little John Forest and borders the Boylston snowmobile trail system Perfect for snowmobiling and 4 wheeling. Acres of state land for hunting. Cabin is 22 miles from the Salmon River in Pulaski NY. Sleeps 4 with a sofa bed and a bunk bed that holds a queen and full mattress. Equipped with electricity, running water,WIFI. A bathroom with shower.

Top Guest favourite
A welcoming living area is presented with wooden walls and floors, featuring a pair of rocking chairs positioned around a small table. A dark wooden cabinet is visible, while a large window allows natural light to illuminate the space, offering a view of the outside landscape.
Cabin in Constableville
4.91 out of 5 average rating, 249 reviews

Summer and winter paradise getaway

Quiet, private, on atv trail. With a large pond. Close to Snow ridge for skiing. Old forge a short drive away approximately 30 min. Steak and brew restaurant only miles away. Fishing , hiking also close.Beautiful perennial gardens. Large yard. Secluded on 5 acres. The cabin is approximately 150 ft from the rd. We are dog friendly. Come stay. You won't be disappointed.

Top Guest favourite
A rustic cabin is set against a backdrop of greenery. The wooden exterior features a metal roof, with a covered porch supported by wooden posts. Windows with green shutters complement the natural surroundings, providing a serene outdoor ambiance.
Cabin in Richland
4.94 out of 5 average rating, 321 reviews

Cozy Cabin near Salmon River Falls

Extra guest fee of $30.00 per person will be applied during booking. Pet fee will be applied during booking process. Pet fee is $15.00 Located near Salmon River Falls, Fish Hatchery, Salmon River and Reservoir. Easy access to Salmon and Steelhead fishing, ATV trails and Snowmobile trails. Additional charges may apply for additional guests and pets during booking process.

Guest favourite
Apartment in Lowville
5 out of 5 average rating, 7 reviews

Collins Street Studio Apartment Pet Friendly

Collins street studio is just a stroll down the street to the center of town where you will find everything our small town has to offer. Favorite places to eat are just a walk away JEBS, Tony Harper’s Pizza and Clam Shack or Crumbs Bakery. The local vet clinic is 1.3 miles away with the nearest Walmart 1.5 miles away The Studio apartment is pet friendly (we love dogs)

Top Guest favourite
A spacious two-story house is presented, featuring a light-colored exterior with a metal roof. A well-kept lawn surrounds the property, and a stone pathway leads to a welcoming entrance. Various satellite dishes are visible along one side of the home.
Guest suite in Boonville
4.97 out of 5 average rating, 71 reviews

Farmhouse Stay on Tug Hill

Perfect for those weekend trips to Tug Hill for snowmobiling or skiing! Enjoy a private 1 bedroom space with a 3/4 bathroom, kitchen, living and dining area. We have a large driveway with plenty of space for parking. Be weary of weather and plan your stay accordingly as this is an area that averages 194 inches of snowfall each year!

Popular amenities for Osceola holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Lewis County
  5. Osceola