Family-friendly holiday rentals in South Hill

4.96 out of 5 average rating, 111 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.

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Guest favourite

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.

4.91 out of 5 average rating, 221 reviews

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!

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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, 114 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

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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, 242 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.

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The exterior view reveals a charming, white clapboard apartment with a covered porch featuring two chairs and a small cafe table. Lush greenery and flowering shrubs border the well-maintained lawn, providing a serene setting for relaxation.

4.96 out of 5 average rating, 631 reviews

Charming, Downtown and Conveniently Located

The Best of Both Worlds- Our charming, Fall Creek apartment is conveniently located just blocks from the Commons/Restaurant Row & around the corner from Cascadilla Gorge, a beautiful trail leading up to Cornell. Perfect for couples, families, solo adventurers & LGBTQ friendly. Convenient, off street parking, separate entrance with outdoor patio area- perfect for your morning coffee or evening glass of wine. Full eat-in kitchen and side porch with cafe table seating.

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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, 223 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.

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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.

4.94 out of 5 average rating, 687 reviews

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.

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Guest favourite

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.

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4.98 out of 5 average rating, 124 reviews

The rustic cabin is nestled amidst lush greenery, with a wraparound deck overlooking the tranquil Cayuta Creek. Steps lead up to the deck, where a shaded picnic table is situated. The natural surroundings enhance the serene atmosphere of this charming retreat.

Cabin in Van Etten

Creekside Cabin

A cozy cabin on the banks of Cayuta Creek, immersed in natural beauty. Located on our 75 acre organic orchard and cidery, it is a short drive to Ithaca, Watkins Glen, Finger Lakes wineries, state parks and gorges. Nature surrounds you: water rushing, a tree frog chorus, beavers swimming by, bald eagles fishing trout. Enjoy hanging out and eating meals on a wraparound deck overlooking the water. Easy access, remote feeling.*Composting toilet*

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4.97 out of 5 average rating, 159 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.

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5.0 out of 5 average rating, 104 reviews

10 min to Ithaca • Green Retreat • Infrared Sauna

Unwind in your private Sunlighten infrared sauna at this peaceful, eco-conscious retreat 10 minutes from the Ithaca Commons. Premium mattresses, deep tub, fully updated 3BR/2BA, and spacious kitchen. A calm, clean space to recharge after exploring the Finger Lakes - minutes from Cornell, Ithaca College, waterfalls, gorges, and Finger Lakes wine country. Note: One half of a quiet duplex – private entrance, parking, and sauna.

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Guest favourite

A vibrant garden scene features clusters of pink and purple flowers, with tall green foliage surrounding them. Sunlight filters through the leaves, illuminating the colorful blooms and creating a natural, serene environment.