Family-friendly holiday rentals in Tompkins County

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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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!

Indoor spacesFamilyAir conditioning

4.86 out of 5 average rating, 461 reviews

An open living area features green cabinetry and a modern kitchen. Skylights enhance natural light, illuminating a blue sofa and a seating area with a wooden table. Large windows provide views of the surrounding landscape, creating a bright and inviting space.

Guesthouse in Ithaca

Ithaca Ski Country Great Escape Mins to Cornell U

Enjoy this beautiful, green guest house mins to Cornell U,(5 Min) & downtown Ithaca(10 Min). CNN has ranked Ithaca as the nmbr 1 town to visit. Short drive to Greek Peak Ski Resort, newly built, 1 bdrm cottage features separate entrance, deck, green bamboo flrs, solar electric heat & air conditioning. It is surrounded by 22 acres of beautiful woods & rolling lawns. Inside enjoy the open flr plan including a ktchn w/ quartz/recycled glass countertop & a ceramic tiled bath featuring a rain shwr.

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Superhost

A spacious interior is characterized by hardwood floors and high ceilings, featuring arrangements of various seating options, including a patterned chair and a futon. The natural light from large windows enhances the comfortable atmosphere, while bookshelves and decorative items add interest to the room.

4.95 out of 5 average rating, 614 reviews

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!

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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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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, 184 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.

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A cozy bedroom is highlighted by a queen bed with patterned bedding and colorful accent pillows. Natural light filters through large windows, offering a view of greenery outside. A nightstand beside the bed features a decorative lamp and a small container.

4.88 out of 5 average rating, 278 reviews

Ithaca Falls View Apartment

Beautiful, private location at the top of Ithaca Falls. A bedroom with a queen bed for 2, a sofa that can sleep 1, a private bathroom, and living room. There is no kitchen or dining room, but there is a a small dining table, two chairs, a microwave, a coffeemaker with coffee, filters, disposable tableware, a toaster, and a mini-fridge (in the closet). It is a 5-minute drive to downtown Ithaca and Cornell University. Ithaca can easily be reached by car, bike, bus, or foot.

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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.

Indoor spacesFamilyHeating

4.92 out of 5 average rating, 152 reviews

A vintage cottage with a pastel pink exterior features two levels of porches adorned with white railings. Lush hydrangea bushes surround the base, and an American flag is displayed prominently. Sturdy stairs lead up to the upper porch, inviting guests to enjoy the scenic surroundings.

Cottage in Ithaca

West Shore, Cayuga Lake, Ithaca, NY

Beautiful vintage cottage at lake level in historical “Cottage Row”, 3 miles from downtown Ithaca. Cottage has upper and lower porches, dock, fire-pit, BBQ grill, and kayaks. Pets considered. Cozy cottage sleeps 6 people. Upstairs is one large space with 2 bunk-beds and a Queen bed. Downstairs futon chair pulls out for single bed. Air Mattress also available if needed. Cornell and IC Graduation weekends: $500 per night/4 night minimum

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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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A lush green hillside is presented, dotted with trees of varying heights. In the distance, a waterfall is visible, cascading down the mountainous terrain, surrounded by a vibrant forest backdrop under a gentle, overcast sky.