Family-friendly holiday rentals in South Hill

4.96 out of 5 average rating, 109 reviews

A red railway caboose is nestled among tall trees and bright yellow flowers. Grass surrounds the property, creating a natural setting that invites exploration. The exterior features windows and a small porch, with the rustic charm of the train architecture evident throughout.

Train in Ithaca

The Cozy Caboose!

This newly-renovated, air conditioned 1953 D&H railway baywindow caboose features barnwood wainscoting, tiled shower, bunk beds, futon, sofa opening to double bed, and kitchenette. The rural property 7 miles outside of Ithaca is one mile from Robert Treman State Park where you can swim beneath the waterfall. Railway memorabilia and railroad-themed books for adults and children enhance the experience. Listed price is for two guests; $25 fee added for each additional guest. Continental breakfast.

4.91 out of 5 average rating, 219 reviews

A wooden dock extends over calm waters, featuring two adirondack chairs positioned for lake views. A flower pot adds a touch of greenery, while distant hills create a serene backdrop. Sunlight reflects off the water under a partly cloudy sky, enhancing the tranquil environment.

Apartment in Ithaca

Cayuga Lakefront Getaway

Enjoy waterfront living in this charming, comfortable apartment on spectacular Cayuga Lake in Ithaca. This private apartment is upstairs in a home that is directly on the east shore of the lake, only 1.5 miles from downtown Ithaca. Enjoy everything Ithaca has to offer-- hiking, Ithaca Commons, Cornell U, Ithaca College, movies and theater, restaurants, the farmer's market, the waterfront trail, wineries-- all within a few minutes' drive of your rental. Or, relax at home and live the lake life!

4.92 out of 5 average rating, 370 reviews

A bright and modern kitchen features white cabinetry and stainless steel appliances. Natural light streams through the windows, illuminating the spacious layout. A yellow accent towel adds a pop of color, while a patterned rug complements the hardwood flooring.

Townhouse in Ithaca

1890s Italianate | Family-Friendly 3BR

Prime Location! This family-friendly home is situated right across from the picturesque Cascadilla Gorge Trail and only 0.4 miles away from downtown Ithaca and restaurants on The Commons. Just down the hill from Cornell University. The home was partially renovated in 2022 and boasts a clean, modern decor throughout. The first floor is furnished with families in mind, providing plenty of space for children to play. Ideal for up to 4 adults or a family of 5. City of Ithaca STR Permit # 25-28

A dining area features a large rectangular table surrounded by six modern chairs. An elegant chandelier hangs from the ceiling, and natural light enters through two doors. A patterned rug lies beneath the table, and wooden cabinets are positioned against the walls.

4.9 out of 5 average rating, 166 reviews

Classic Charm, Modern Comfort

Escape to a charming historic home with original woodwork and modern accents. Perfect for a cozy getaway or as a home base for outdoor adventures. Enjoy the vibrancy of downtown living, close to nature! Located just around the corner from popular Gimme Coffee Shop, Ramen, Pizza, Bars, Breweries + more! City of Ithaca #STR-25-62 5 min drive to Cornell, Farmers Market, Trader Joes 10 min walk to Ithaca Commons <10 min drive to Ithaca College, hiking gorges, shopping, grocery + wineries

The exterior showcases a modern wooden facade with large windows that invite natural light. A landscaped area with gravel and wooden fencing creates a welcoming entrance, framed by tall trees against a clear blue sky.

5.0 out of 5 average rating, 112 reviews

Downtown Ithaca New Build – Award-Winning Stay

Welcome to our beautifully designed, freshly built ADU—a 2024 Pride of Ownership Award recipient! This one-of-a-kind downtown retreat is perfect for visiting families, couples, and professionals seeking an authentic Ithacan getaway. Enjoy inviting living spaces, a well-appointed kitchen, and a private outdoor area to unwind. Nestled in a convenient location, you are moments away from parks, restaurants, universities, and local attractions. City of Ithaca STR Permit Number STR-25-1

Aerial view of a lakeside property featuring a red dock with a picnic table and green umbrella. A fire pit and seating areas are visible on the shore, surrounded by lush greenery. The house, with multiple decks, is nestled among the trees in the background.

4.95 out of 5 average rating, 183 reviews

Magical lakefront treehouse, minutes to downtown

A magical treehouse perched over its own gorge on Cayuga Lake. This place is special! There’s a giant porch wrapped around a 300-year oak tree and a lakeside tea house that can serve as an extra bedroom. There’s a dock, fire pit, room for yard games by the water, plenty of outdoor seating on the porch, by the lake, or on the dock. All of this is minutes from downtown Ithaca, Cornell, and Taughannock Falls state park. It’s also a great base to explore the Finger Lakes wine region.

The cottage exterior is framed by lush greenery and mature trees, showcasing a welcoming front porch. A white railing borders the porch, which features comfortable seating. A distinctive chimney and large windows enhance the inviting aspect of this charming home.

4.92 out of 5 average rating, 241 reviews

Craftsman cottage near Cornell & Cayuga wine trail

Welcome to the upstate cottage of your dreams! This petite charmer has been tastefully renovated to curate a boutique guest experience. Enjoy cooking meals in the sunny gourmet kitchen, spinning 45s on the turntable, drinking coffee on the front porch, or relaxing on the patio by a wood-burning chiminea. Fully-fenced yard with mature trees & bistro lighting, main floor king bed & bath, two living rooms, two fireplaces! Minutes to downtown, hiking, waterfalls, IC, Cornell.

A cozy living area features a woven chair framing a view of a large television displaying a scenic image. Two comfortable armchairs are positioned nearby, with a round coffee table placed in the center. Natural light filters through sheer curtains, illuminating the textured area rug.

4.98 out of 5 average rating, 220 reviews

Boho House- A Rural Escape with Fire Pit, EV, WFH

Discover Boho House, a charming 3-bedroom, 2-bath modern bohemian sanctuary in rural Ithaca, just minutes from downtown. This newly built home comfortably features comfortable beds, dedicated desk with dual monitors, fast Wi-Fi, an outdoor oasis with a fire pit and BBQ and a shared pond with hammocks. Perfect for families, remote workers, and nature lovers seeking a peaceful escape. *Note that the home is 1/2 of a duplex. Indoor and outdoor spaces are private.

4.94 out of 5 average rating, 684 reviews

A cozy seating area is adorned with a gray sofa featuring orange accent pillows and a warm throw blanket. A wooden coffee table with a cushioned top sits in front, complemented by a colorful chair and a standing lamp that provides soft illumination.

Apartment in Ithaca

Sweet Country 3 Bedroom Apartment

There is a 2 nite min. stay for most weekends. The price listed is for 2 guests. Each additional guest, after the first 2, will be $30/nite (reflected in quote when you enter the correct # of guests.) Beautiful 8-12 minute drive to downtown, Cornell & IC. The 3 bedrooms include a queen room on 1st fl. & queen & twin rooms on 2nd fl. Full, modern kitchen w/ stove/oven, microwave, dishwasher. WiFi, movie channels on the 2 TVs, small deck, 2 umbrella tables.

4.94 out of 5 average rating, 110 reviews

Family-Friendly Retreat near Cornell & Downtown

Welcome to our family-friendly retreat near Cornell & Ithaca College! Enjoy one-level living with a sunny backyard, close to parks, trails, and downtown. Perfect for families and groups visiting Ithaca. The upper unit shares a front entry with the lower unit but has its own private indoor entrance for full privacy and comfort. Relax in a bright, open living space with a fully equipped kitchen, fast Wi-Fi, free parking, and everything you need for a cozy stay.

4.97 out of 5 average rating, 153 reviews

A grand historic home is presented with tall columns and a spacious front porch. Symmetrical windows adorned with green shutters frame the entrance, which features a traditional door. Flower beds bloom at the base of the columns, enhancing the home's charming exterior.

Guest suite in Ithaca

Guest Suite at Chauncey House

Join us for a stay in our historically grand 1835 home, perfectly located in the heart of Downtown Ithaca. Everything you’re looking for is only a few walkable blocks away: Moosewood & shopping at Dewitt Mall – 1 block. Shopping & Events in Ithaca Commons – 2 blocks. Restaurant Row on Aurora Street – 3 blocks. Ithaca Farmers Market – 1 mile. If you're visiting students, Cornell University and Ithaca College are both nearby.