Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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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 Redfield

4.89 out of 5 average rating, 19 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!!

Superhost

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, 87 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 favorite

A cozy living area is visible with a comfortable sofa draped in a red and black plaid blanket. A decorative area rug lies on the floor, while large windows framed by dark curtains allow natural light to brighten the space. A wall-mounted television and a wooden fireplace unit enhance the ambiance.

Apartment in Camden

4.97 out of 5 average rating, 101 reviews

*Small Town Charm-Vacation rental 🎣 🐾🏡Sleeps 6*

Beautiful 1/2 house! 2 bdrms upstairs, living, kitchen, laundry and bathroom downstairs. House was built in the late 1800s and this side of the house boasts the original stair case and railing which is exquisite. Custom made bar/island top. Kitchen is stocked with appliances, dishes, cutlery, pots/pans and more. Perfect place to stay with the family, the girls or the guys for a fishing trip! Central to Salmon and Oneida lake fishing! Forest park is a fabulous place to bike or walk as well!!

Top guest favorite

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, 232 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 favorite

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

4.99 out of 5 average rating, 167 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!

Superhost

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

4.79 out of 5 average rating, 24 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, 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.

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 Redfield

4.95 out of 5 average rating, 20 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

5 out of 5 average rating, 19 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

4.76 out of 5 average rating, 38 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

A charming house is set against a backdrop of greenery, featuring a covered front porch with steps leading up to the entrance. Well-maintained lawn space surrounds the home, complemented by flower beds. A small playset can be viewed to the side of the property.

Cabin in Williamstown

4.91 out of 5 average rating, 22 reviews

Redfield Retreat

Enjoy the summer hike to the Salmon River Waterfall 18 minute drive. 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. Ride your snowmobile from the house, the trail is half mile away on Ryan Road.

Top guest favorite

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, 474 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.

Guest favorite

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, 243 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.