Vacation rentals in Trumansburg

Cozy Cabin in the Sky

Our Skyview Cabin at Hillside Haven is a 1 room, 1 bath Cabin lifted 12ft in the air. Offering a unique experience of cozy and comfortable, with Treehouse heights. The cabin boasts a fully functional kitchenette, and indoor gas fireplace, and a queen size bed. Outdoors at ground level you'll find a private canvas enclosed patio with a gas fireplace, and a charcoal grill. Close to The Fingerlakes National Forest, Seneca and Cayuga Wine Trails, and some of New Yorks most beautiful Waterfalls!

Historic Village Retreat: 2 BR home near Main St.

This 2 bedroom, 1 bath home is located in the charming, historic village of Trumansburg. It is all on 1 level and consists of a living room, cozy reading den, spacious kitchen, full bath, and 2 bedrooms, as well as an outdoor patio space, and an inviting porch to relax on and sip your morning coffee. Enjoy hi-speed wi-fi as well as complimentary coffee & tea. Take a short stroll to restaurants, the farmers market, shops, and a brewery. It is a close drive to state parks, wineries, IC, & Cornell.

Finger Lakes Vintage Airstream Glamping For 2

Discover the perfect blend of vintage charm and modern comfort in "FLO", our remodeled airstream, located just outside Trumansburg NY. Nestled in the heart of the Finger Lakes, this glamping experience is ideal for couples or friends seeking a unique seasonal getaway. Trumansburg is fairly rural and you'll need a car to fully explore the area. You'll be close to state parks and award-winning wineries. Explore local waterfalls, farmers markets, hiking trails and the vibrant town of Ithaca.

The Hillside Loft

More photos coming soon. 15 Minutes to Cornell and IC. Enjoy peace and quiet with views of the rolling hills in this brand new apartment built in 2026. With two king bedrooms and a spacious living room you’ll be at home in this professionally designed apartment. Comfortable beds, a coffee bar with Starbucks pods and luxurious finishes, this apartment is your perfect destination when visiting Ithaca. The apartment is on the 2nd floor of a building with our property management office downstairs.

Waterfall retreat

Sleep to the sound of your private waterfall in this cabin made for two. 12 miles from Ithaca and central to all that the Fingerlakes has to offer, less than one mile from the only National Forest in New York State, a 15 minute drive to either Seneca or Cayuga lakes, Waterfalls, and of course the renowned wine trails. This cabin is equipped with high-speed wifi, climate control with AC, hot/cold water, flush toilet. Fold-out couch in the living room for a third guest (fee). Grown-ups only

Stylish creek view suite on Main Street

This special place is walkable to shops, restaurants, bowling, golf, and a short drive to the wine trails and state parks. Enjoy your favorite eatery’s “to go” in your private back space or sip on local coffee/wine/beer while listening to the sounds of the creek. The cozy space has all the amenities to mimic a hotel suite, but with its own private entrance. Ideal for one or two guests, but can accommodate three by folding couch into a futon or we can leave a twin air mattress upon request.

King Bed, Cornell, Ithaca, WineTrail, Hiking

Enjoy a romantic getaway in this beautiful 1 King bedroom, located close to Ithaca, Trumansburg and both the Cayuga and Seneca Lake Wine Trails. This newly built house provides all the modern amenities with a country feel. It is set back off the road with private parking and a private fenced in back yard. Only minutes from Taughannock Falls State Park and a 30 minute drive to Watkins Glen State Park, this is the perfect place to watch the sunsets from the large windows with a glass or wine!

Carriage house

Have the best of both worlds in this private, fully renovated one bedroom carriage house, with fully stocked kitchen. Located on a low traffic, quiet road for your perfect weekend getaway to Ithaca. Close to restaurants and shopping. Within walking distance to Cayuga Hospital. Five minute drive to the Commons and ten minute drive the Cornell University or Ithaca College. You do have to walk about 50 ft through my grass so if it rains, you might want to bring some old shoes.

"Red Tail Cabin" at Hawks Nest

"The Red Tail" is a spacious 2- bedroom cabin located in the heart of the Fingerlakes in Upstate New York. If you are looking to get away from noise and enjoy the solitude of nature, this is the place for you! The cabin is close to hiking trails. wineries and breweries on both Cayuga and Seneca Lake. Close proximity to Trumansburg, Lodi and Ovid and 17 miles to Watkins Glen and Ithaca. Plenty of on premise parking Electric fireplace Washer/Dryer Covered porch Outdoor Grill

Walk to Main St | 112 Five Star Reviews

Soak up small-town life in Trumansburg, NY! Wake up in this sweet & simple Main Street apartment, steps from Gimme! Coffee, Creekside Cafe, and local shops. Summer awaits — wine taste along Cayuga Wine Trail, swim or kayak on Cayuga Lake, hike to stunning Taughannock Falls. Day trip to Cornell or Ithaca's gorges. Return for local brews, open mic, bowling or NY pizza. Kids love the playground, library & ice cream. Your perfect Finger Lakes summer escape!

Modern ‘Barn-dominium’ in the Village

A short walk to the charming village of Trumansburg, NY, this studio-like guest suite is perfectly situated near lakeside wineries, beautiful Taughannock Falls, numerous hiking trails, Cornell University and Ithaca College. The Barndominium provides an opportunity for a lovely country getaway, with modern amenities (including free wi-fi) within reach – restaurants, bars, shops, coffee, ice-cream and a full-service grocery store are all nearby.

Maple Grove Yurt at Finger Lakes Cider House!

Welcome to The Maple Grove Yurt! Our newly handcrafted yurt at Finger Lakes Cider House was completed May 2025. This all-season, round cabin is nestled creekside in our maple grove. Every detail is custom- built by our Cider House crew. This little hobbit house sits on our 70 acre property of regenerative pasture, forest, and apple orchards— shared with our grass-fed flocks and herds of turkey, chicken, pigs, sheep, and white angus.