Family-friendly holiday rentals in Ulysses Town

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.

The Lakeview Nook – Midcentury Modern Stay

Enjoy this mid-century modern guest house in a spectacular site, with a lake view, waterfall, and forest all in one place. The house was just fully renovated. This house is just 2 miles from Ithaca downtown and 3 miles from Cornell University. The location is super close to everything Ithaca has to offer—Ithaca falls, downtown, restaurants, the farmer's market, wineries, all within a few minutes drive of your rental. This unit is fully private, with no shared areas/entrance with the other unit.

Rustic Retreat- Hiking,waterfalls,wineries,CU,IC

Enjoy your next Finger Lakes vacation at the Rustic Red Retreat! Located just outside of Ithaca, and a short drive to Cornell, this home is nestled next to a peaceful pond and provides modern amenities with rustic charm. The beautiful hand-hewn beams, reclaimed materials, and fireplace offer a warm, cozy stay after a busy day exploring the area. Enjoy numerous state parks, incredible waterfalls, wineries, breweries, restaurants, and all the seasonal events that the Finger Lakes have to offer!

Hayt's Chapel

Hayts Chapel, on a beautiful and private half acre has a large open space with hardwood floors, high ceilings, partitioned bedroom, full bathroom, and kitchen. Large old windows with wavy glass let in tons of light, but insulated attic keeps it cool. Outdoors has an eating area, stone fire pit, and plenty of parking. Close to downtown, gorges, wineries and u-pick farms, this quiet setting with relaxing ambiance is a wonderful space for a home-base while visiting Ithaca and the Fingerlakes!

Bitty Bot - the Cutest Tiny House in Trumansburg

Welcome to Bitty Bot, our Greek Revival tiny house. This structure was built in part by Hammerstone: Carpentry for Women classes, and finished by our women owned contracting crew. This micro sized tiny house is the perfect way to find out if tiny living is a good fit for you. Plenty of light and beautiful detailing, along with views of the neighboring farm make this tiny space feel warmly welcoming! Enjoy a rural getaway with chickens and a cider orchard. PLEASE READ IMPORTANT NOTES

Peaceful Getaway mins from Lake and City

Pet friendly, great for short and long stays. Queen size bed, sofa couch and futon. Pond, fire pit, and large shared deck. Smart TV w/cable you can also connect your computer/device to for streaming. HDMI cable is provided. Excellent location close to lake, Cornell University, Ithaca College and minutes from downtown Ithaca and Cayuga Lake. Only 30 minutes from Greek Peek Skiing. Committed to keeping you healthy, safe, and comfortable. Apartment is sanitized after each guest stay.

The Barn Manor with Manners: Barndo with Love!

Experience luxury at Barn Manor, a converted barn surrounded by fields and forests. Relax in a jetted tub with heated floors, enjoy fireside evenings, and admire custom woodwork, marble accents, indoor hammock and unique windows. Both levels are open floor plans: the first floor has a queen bed, full kitchen, living space, and bathroom; upstairs offers a king bed with Casper mattress, queen futon, and optional fold-out twin. Sleeps up to 8. Ask about long-term winter stays.

The Pink Lady - Houseboat on Cayuga Lake!

Efficiency at its best! Custom-designed houseboat with sweeping views of Lansing Harbor. Marine toilet in unit with full toilet across parking lot. Showers, laundry, and marina store are just a short walk away. The perfect getaway! Easy access to Ithaca, Aurora, wineries, and breweries. Be sure to also book one of our BRAND-NEW pontoon rentals during your stay to access Taughannock Falls State Park, Boatyard Grill, Ithaca Farmer’s Market, wineries & more by water!

Artists' Paradise: Waterburg Chapel

Retreat to the country in this beautifully restored 19th c. Greek Revival church located in the quaint hamlet of Waterburg, a 5-minute drive from the Village of Trumansburg and a 12-minute drive to Ithaca in the heart of Finger Lakes wine country. I prefer a 3 night stay but on certain dates could do 2 nights - never hurts to ask! Subletting the church from November 1, 2025 to May 1, 2026, any or all of this time.$1350 per month. message me for details.