Holiday rentals in Jacksonville

Boho room with King bed at New Park, a picturesque

Book this sweet, romantic room with gorgeous stained glass windows and a king bed. The Lower Bunk has a king bed, eating area, kitchenette (microwave, refrigerator and pod coffee machine), and cozy cabin walls. This room is the perfect getaway for early risers who want to get out and explore! An enormous stained glass window faces the eastern side of the room and radiates through the room with the rise of the sun. Enjoy the morning basking with an assortment of compostable coffee pods, and

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.

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

Hot Tub | Posh Retreat near Cornell & Wine Trail

Step into the comfort of this quaint 3BR 2BA gem nestled in between Trumansburg and Ithaca, perfect for escaping big-city crowds while just a few mins from Cornell, Ithaca, Cayuga, and Seneca Lakes, and the Cayuga Lake Wine Trail! Explore the region from this prime location; our fantastic oasis will be waiting for you whenever you want to recharge. ✔ 3 Comfortable Bedrooms ✔ Living Room & Den ✔ Full Kitchen ✔ Backyard (Hot Tub, Fire Pit) ✔ Smart TV ✔ Wi-Fi ✔ Parking See more below

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.

The Barn Manor with Manners: Barndo with Love!

Experience luxury at Barn Manor, a stylishly converted barn nestled in nature. Relax in a two-person jetted tub with a heated floor, admire unique live-edge woodwork, and sleep soundly in a king or queen bed. Suitable for up to eight guests. Enjoy fireside moments outdoors while surrounded by fields and forests. Discover your ultimate countryside sanctuary at Barn Manor with Manners. Please inquire about discounted long term stays over the winter season.

The Timber Garden Cottage

This stunning home is waiting for you! It has classic timber frame construction boasting large beautiful wood beams, lots of light, and a rustic feel. Both spacious and cozy at the same time! Located centrally to all things Ithaca, 7-10 mins drive to downtown, 15 mins to both Cornell and Ithaca College, and a few miles to Taughannock State Park, the beginning of the Cayuga Wine trail, and Trumansburg. This cottage puts you close to all things Ithaca!