Holiday houses in Cortland County

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Top-rated holiday rentals in Cortland County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a charming yellow duplex features green shutters and decorative architectural elements. A white chair and a small flag are positioned on the porch, with a well-maintained front yard showcasing grass and landscaping. A sidewalk leads alongside the house.
Home in Homer
4.95 out of 5 average rating, 85 reviews

Farmhouse on Fulton

Farmhouse on Fulton is a duplex located in the heart of the village of Homer, NY. Just a few blocks from the Center 4 the Arts, the village green, school playground, restaurants, bakeries, the library, and a few lovely local shops. Homer is a picturesque village taken right out of a Hallmark movie. Two miles from Cortland and a short drive to Ithaca, Syracuse, easy access to I-81, the Finger Lakes Region, local breweries and wineries, 3 different ski resorts, indoor waterpark, golf courses.

Top Guest favourite
Apartment in Cortland
5 out of 5 average rating, 17 reviews

The Doxtader

It's all about Location, Location, Location! Enjoy a stylish experience at this centrally-located condo right at the bottom of the Greek Peak ski mountain. You can ski-in/ski- out! This recently renovated studio has an electric fireplace, new queen sofa bed, full-size kitchen, and even a dry sauna off the bathroom. Betsy did a fabulous job making this small unit into a beautiful space whether it be a romantic get-away, a wedding weekend, fishing/hunting or fun on the slopes. You'll love it!

Guest favourite
Chalet in Willet
4.94 out of 5 average rating, 156 reviews

Lakefront Retreat: Hike, Fish, Campfires, Kayaks

Welcome to Sunset Chalet — your private lakeside escape. Set on peaceful waterfront property, this cozy retreat is perfect for relaxing and enjoying nature. Swim in the private pond, kayak on the lake, explore trails, or unwind around the fire pit under the stars. Enjoy: • Lake access • Private swimming pond • 2 kayaks + canoe • Fire pit • Private setting Close to Greek Peak, Ithaca, waterfalls, hiking, and Finger Lakes wine trails. Reserve early — summer and peak weekends book quickly.

Top Guest favourite
A private fire pit area is set on lush green grass, surrounded by several light wooden chairs. In the background, Song Lake glistens under the sun, and a private dock extends into the water, providing access to the serene scenery.
Cottage in Tully
4.95 out of 5 average rating, 375 reviews

Lakefront Getaway - Relax & recharge on Song Lake!

Private lakefront getaway on Song Lake! Spectacular rural setting with room to roam. Enjoy views of autumn foliage by day, relax by the firepit at night! Private deck & dock - bring your kayak and fishing gear! Fully equipped kitchen. Outdoor gas grill. 5 min to Onco brewery. 2 min to Heuga's Alpine & Song Mountain. Ski/snowmobile in winter. Year round access to Finger Lakes wineries, breweries, spas. 25 min to charming Skaneateles dining & shopping. Near 6 colleges including Cornell & SU.

Top Guest favourite
A charming historic house is displayed, featuring a light exterior with decorative trim. A sloped roof and front porch with steps lead to the entrance. Lush green shrubs line the base of the house, complemented by trees in the background, suggesting a peaceful residential setting.
Home in Cortland
4.98 out of 5 average rating, 161 reviews

Adorable 2-bedroom home

Adorable home built in 1890 and renovated in 2019. Easy on/off from I-81, centrally located in New York- making it a great location to stay while visiting multiple colleges in one trip. Including SUNY Cortland, TC3 (~15min), Syracuse University(~30 min), Cornell (~30 min) & Ithaca College (~40 min) *Walking distance to: SUNY Cortland Downtown/Mainstreet Cortland Starbucks Several amazing local restaurants & a grocery store. Great local ski options including Greek Peak and Labrador Mtn.

Top Guest favourite
A firepit surrounded by five blue Adirondack chairs is positioned on a lush green lawn. The tranquil reflection of trees and hills can be seen in the lake, creating a serene backdrop as the sunset casts a warm glow over the scene.
Cottage in Little York
4.98 out of 5 average rating, 117 reviews

Lakefront Escape: Kayaks/Firepit

Escape to this cozy all seasons lakefront cottage on Little York Lake! This charming retreat offers a perfect blend of tranquility, adventure and picturesque views no matter the season. Enjoy direct lake access for swimming, kayaking, and serene moments. In winter, hit nearby slopes for skiing, or go ice fishing on the lake, returning to our charming cottage for a fireside retreat. This ultimate lakeside getaway for all seasons is an ideal choice for a couple, family or a group of friends.

Top Guest favourite
Apartment in Cortland
4.96 out of 5 average rating, 26 reviews

The Lunchroom - Historic Railroad Stay

Step into a space where history, comfort, and charm meet. Once home to Madden’s Lunchroom (est. 1905), this thoughtfully renovated 19th-century building once served warm meals, cigars, and pies to railway travelers in Cortland before dining cars existed. Today, The Lunchroom is a one-bedroom apartment blending timeless character with modern ease. Just 2 blocks from Main Street & under a mile from SUNY Cortland, it offers unbeatable walkability to restaurants, bars, and campus events.

Top Guest favourite
A two-story white house is framed by green shutters and a welcoming front porch. The yard features a light dusting of snow, with patches of grass visible. Trees provide shade while a driveway leads to a parked blue vehicle in the background.
Guest suite in Cortland
4.86 out of 5 average rating, 171 reviews

Conveniently located private suite in Central NY

Clean, comfortable, one-bedroom suite located in one of the best areas of Cortland! Only a 5-min walk to Yaman park where you can sit down for a nice picnic, swim in the beach area, fish, or kayak in the Tioughnioga river. Easy commute to Syracuse 40 mins or Ithaca. Located 40mins to 8 golf courses, and 4 ski resorts. Walking distance to grocery stores, laundromat, coffee shop, restaurants, a fitness center, bus route, and city owned rental bikes all located within just a few minutes.

Superhost
Tiny home in Marathon
4.94 out of 5 average rating, 90 reviews

Hoxie Haven | Glamping in the Gorge |

NOTE: temps below 20° may mean no running water in the bathhouse. Camp toilet stays usable. Nestled by a stream at the foot of a hill, alongside Hoxie Gorge State Forest, near the head of Hoxie Gorge Trail & Finger Lakes Trail; only 9 miles from Greek Peak Ski Resort, this tiny house A-Frame is a year-round glamping escape you don’t want to miss. This unique and cozy space is ideal for couples or solo trips. Equipped with a mini fridge, toaster oven/air fryer, microwave and kuerig.

Guest favourite
A cozy living area is presented with a light-colored sofa adorned with yellow accent pillows. A decorative cabinet with an electric fireplace is positioned against the wall. Natural light filters through a window dressed with blue curtains, illuminating a patterned rug on the floor.
Farm stay in Virgil
4.93 out of 5 average rating, 113 reviews

Country Chic B&B near Ski Resort. Spacious 2br3bth

This stylish place is close to must-see destinations. Greek Peak ski resort with all season attractions, Suny State and Cornell University, Fingerlakes wine trails. This property boasts 2 large bedrooms with a spacious open concept living and dining area. Spectacular views from indoors and around the 6 acre grounds. Full renovation underway with all new floors, appliances, bathrooms, state of the art lighting and country chic decor. Pet friendly!

Guest favourite
A white farmhouse with classic black accents is set against a backdrop of lush green grass and trees. The two-story building features a welcoming front porch and large windows, while a distant church spire can be seen through the trees.
Farm stay in Cortlandville
4.96 out of 5 average rating, 173 reviews

1820's Quaint Rustic Farmhouse

Beautiful, spacious, two-bedroom private suite. The Farmhouse is located on 50 acres of farmland in our beautiful river valley. We are directly off the Cortland I-81 exit and are 30 minutes to Cornell, Ithaca and Syracuse. We are conveniently located near Greek Peak and other local ski areas. Great location for professors, parents, students, outdoor enthusiast and anyone exploring the Finger lakes! We hope you enjoy your stay and come back again.

Superhost
A spacious living area features a dark green sectional sofa adorned with colorful pillows. Light hardwood flooring is complemented by a patterned area rug. Natural light filters in through large windows, leading to a sunlit porch visible in the background.
Apartment in Cortland
4.85 out of 5 average rating, 52 reviews

Grand Central Ave

Grand Central Ave offers a quiet stay near downtown Cortland NY and SUNY Cortland. Enjoy a New York City themed apartment with many amenities to make your stay more enjoyable. We are approximately 22 minutes to Ithaca NY and about 33 miles to Syracuse NY. You will be near the Finger Lakes region, Watkins Glen and so much more!

Popular amenities for Cortland County holiday rentals