Family-friendly holiday rentals in Penn Yan

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Penn Yan

  • Total holiday rentals

    Explore 50 holiday rentals in Penn Yan

  • Nightly prices starting at

    Penn Yan holiday rentals start at $223 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,470 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Penn Yan holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Penn Yan rentals

  • 4.8 Average rating

    Penn Yan stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Penn Yan

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
Chalet in Penn Yan
4.94 out of 5 average rating, 167 reviews

HUGE Covered Porch ON LAKE-Kayaks/Bikes/Air Hockey

ON THE BEACH offers all the comforts of home! No steps to entry! Right on the water! Dock, boat hoist, kayaks, and bikes! With 3 bedrooms and 2 baths, laundry, a fully stocked kitchen, WIFI, and big screen TV's, you'll feel comfortable immediately. The game room has an XBOX 360, Big Screen TV, & Air Hockey, plus a cozy fireplace. This year round home offers A/C plus ceiling fans in the summer and gas heat in the winter. Close to town, restaurants, wineries, breweries, distilleries, and skiing

Top Guest favourite
Tiny home in Burdett
5.0 out of 5 average rating, 211 reviews

FLX 3- Lake View Wine Country Tiny Cabin

Nestled up on a hill overlooking Seneca Lake, watch the sunset while laying in bed or from your own patio with a fire crackling. We are local hosts and will make sure you have an unforgettable stay! Everything you could want to do in the Finger Lakes will be at your fingertips. Wineries galore, two even just next door, multiple breweries nearby, minutes to the lake, 15 minutes to downtown Watkins Glen, 10 minutes to hiking trails at the national forest, or stay in, relax, and enjoy the view!!

Top Guest favourite
The living room features a comfortable seating arrangement with a leather sofa and a rocking chair. A stone fireplace is centered on the wall, above which a television is mounted. Soft natural light filters through sheer curtains, creating a warm ambiance.
Home in Penn Yan
4.99 out of 5 average rating, 253 reviews

Experience Finger Lakes at The Best of Both Abode

Nestled on the main road just inside Penn Yan, Best of Both Abode is a split-level home in the heart of the Finger Lakes. About 30 minutes to Watkins Glen, Geneva, or Canandaigua. Dozens of wineries, amazing state parks, beautiful lakes, waterfalls, farms, breweries, shopping, and so much more all close by. The perfect place for couples, families, groups of friends, and traveling workers. Enjoy our spacious lawn and deck, or cozy up inside. We invite you to come make yourself feel at home.

Top Guest favourite
Two Adirondack chairs are positioned in a grassy area, accompanied by a small table. The chairs provide a view of the surrounding landscape, which includes trees and hills leading down to water in the distance under an overcast sky.
Guest suite in Penn Yan
4.96 out of 5 average rating, 225 reviews

Overlooking beautiful Keuka: Sunrise to Sunset!

A self-contained apt right in the heart of the beautiful Finger Lakes. Close to Keuka College, parks, restaurants, museums, trails, wineries, and kayak/bike rentals. Room for boats/trailers. Self-check in with lock box Super clean, lower apartment features a private entrance. It has a large bedroom with a comfortable king size bed, convertible to two twins, upon request. Twin/mattresses on floor can sleep up to 2 children ($15 ea) or 1 more adult($40)per night Private bathroom with shower.

Top Guest favourite
A single-story cottage is set among lush greenery, featuring a welcoming front entrance with a blue door. The well-maintained yard includes vibrant shrubs and trees surrounding the home, with a large garage visible to the right, adding to the property’s charm.
Cottage in Penn Yan
4.99 out of 5 average rating, 172 reviews

Blūm on the Hill Cottage in the Finger Lakes

Enjoy a peaceful stay in our cottage located just over 2 miles from the quaint village of Penn Yan on Keuka Lake. Relax in the newly renovated 2 bedroom, 2 full bath home with a fully equipped dine-in kitchen, spacious living room with electric fireplace, and dining room. Enjoy the fresh air on the back deck with Keuka Lake peeking through the trees. Take in the sites of the many trails, vineyards, breweries and state parks in the area during your stay. So just relax, you're on lake time.

Guest favourite
Home in Keuka Park
4.92 out of 5 average rating, 115 reviews

Keuka Gully Cabin

Traveling small? inquire for discount! 10 Acres 2 Trails 4 Breweries and wineries within 5 min 1 Wood burning stove 2 Zone MrCool 4 Bedrooms 5 Lake views 1 washer/dryer 1 Superhost As you drive up the semi-private road, you'll wind through picturesque vineyards and serene woods, arriving at your quiet cabin. The property boasts a tranquil gully, perfect for relaxing, hiking, and simply enjoying nature. The charming Village of Penn Yan is just around the corner, waiting for you to explore.

Guest favourite
A soft blue accent wall frames a cozy sleeping area featuring a spacious bed adorned with white and green decorative pillows. A vase of white roses and yellow flowers rests on a wooden table in the foreground, adding a touch of natural beauty.
Home in Keuka Park
4.92 out of 5 average rating, 270 reviews

Charming Keuka Lake Home Away from Home

Enjoy the Finger Lakes region from this quaint Cape Cod style home located just steps from Keuka Lake. Fondly nicknamed the Blue Iris Inn, this private home offers plenty of living space, a very large kitchen, comfortable private bedrooms, spotless bathrooms, on-site laundry and abounding outdoor space complete with a patio and gas grill. We are in the heart of the Keuka and Seneca Lake Wine & Beer trails and the State Park with beach access is just around the corner. Adventure awaits!

Top Guest favourite
Apartment in Penn Yan
4.97 out of 5 average rating, 134 reviews

Route 54 Relic in Penn Yan.

1880's home now 3 units. Built when steam ships still piloted Keuka. Penn Yan can be accessed by sidewalk from here (approx 1 mile to center), steps from Red Jacket Park at Keuka Lake on one side, Seasons on Keuka Lake on the other. Close to Keuka Outlet Trail, on the Keuka Lake wine trail, and between Main Deck restaurant and Rt 54 (WE ARE NOT WATERFRONT). There is plenty to do between shopping in Penn Yan, hiking the Outlet, or going on a wine tour around Keuka and/or Seneca Lake.

Top Guest favourite
Cabin in Branchport
4.98 out of 5 average rating, 161 reviews

Secluded, Hot Tub, Fire Pit, Deck, Grill, Pets

Discover Creekside Hideaway – the perfect romantic getaway. Nestled by a tranquil creek, this cozy retreat features a private hot tub, a crackling fire pit, and a gas fireplace for ultimate relaxation. Surrounded by nature, it’s ideal for unwinding together, exploring nearby trails, or simply savoring peaceful moments. Whether reconnecting over a fire or soaking under the stars, Creekside Hideaway offers a serene escape to create lasting memories in a secluded, scenic setting.

Top Guest favourite
The kitchen area features modern appliances, including a refrigerator and microwave, alongside a granite countertop. A wooden shelf displays dishware and cooking utensils, while a window allows natural light to fill the space. The rustic wood ceiling complements the white shiplap walls.
Guesthouse in Penn Yan
4.98 out of 5 average rating, 171 reviews

Quiet Guesthouse near Keuka Lake and Penn Yan!

Welcome to our cozy guesthouse! Nestled in the Fingerlakes Region of New York, it's the perfect place to rest after a day spent exploring our beautiful lakes, wineries, hiking trails, and so much more. Our guesthouse is located 2 minutes away from the Keuka Outlet Trail, 5 minutes from Penn Yan and Keuka Lake, and just minutes away from several local wineries. In the winter, we love to visit Bristol Mountain Ski Resort, 45 minutes from us! We can't wait to host you!

Top Guest favourite
A serene lakeside home is positioned on a gently sloping green hill, featuring a spacious deck that overlooks the water. Surrounding trees provide a natural setting. The structure showcases large windows, allowing for abundant natural light and expansive views of the lake.
Home in Penn Yan
4.98 out of 5 average rating, 291 reviews

Beautiful Keuka Lake home close to Penn Yan.

Welcome to Keuka lake in this beautiful home that boasts 3 master suites. The living room has a panoramic view of Keuka Lake. There is a deck off the top floor and a patio off the first floor to sit and enjoy the lake view as well. From the downstairs patio you are only a few steps to the beach. At the end of the dock the lake is only 3 feet deep so it’s excellent for swimming. Everything in this house is new and very clean. We are a mile from downtown Penn Yan.

Top Guest favourite
A bright living area features floor-to-ceiling windows offering views of the lake. A round dining table accommodates four, while a cozy seating arrangement includes a gray couch and two chairs. Natural light floods the space, enhanced by high vaulted ceilings and wood accents.
Home in Jerusalem
4.98 out of 5 average rating, 107 reviews

The Best Getaway on the Keuka Lake Wine Trail

Welcome to our “tree house" paradise on Keuka lake! It's one of the most unique cottages on Keuka. Our lake home promises you an unforgettable vacation on Keuka, with unparalleled views of the lake. Spend your days lounging on the beach, swimming, fishing, kayaking or tasting the local wine & cheese before you wind down on the hammock, taking in breathtaking views among the Keuka treetops. End each night with memories (and S’mores!) ‘round the campfire!

Popular amenities for Penn Yan family-friendly rentals

When is the best time to visit Penn Yan?

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