
Family-friendly holiday rentals in Penn Yan
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Penn Yan
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Crows nest lake view flat
Crows Nest is located on the Keuka Lake wine trail. It is next to Red Jacket Park and Morgan Marine on one side, Seasons on Keuka Lake on the other. Very close to Penn Yan/Yates County Airport and between the Main Deck restaurant and Route 54. The property is NOT water front. Keuka Lake is accessible thru Red Jacket Park and visible from the property, but not directly on the water. There is a sidewalk from the property to town for Guests who prefer to walk, approximately 1 mile to Village center

Farm House Suite 15 minutes from Bristol Mountain
Country location on a quiet road just minutes from Canandaigua Lake, and Bristol Mountain. Large farmhouse, with private suite including a huge great room (450 sf), wrap around screened-in porch. Please note that bedrooms and bath are upstairs. Geothermal heating/cooling. No full kitchen or downstairs sink available, only toaster oven, mini fridge, coffee maker (Keurig) with seating for 4 in section of great room. TV, fast Wifi for all your devices. Plenty of privacy and room to spread out.

Keuka Lake Hilltop Cottage
This is a unique modern home on a beautiful setting. A circular, 15 sided layout with lots of light overlooking Keuka Lake. Well furnished in a country setting. Enjoy the fresh air and quiet. Internet from TMobile 5G. No network TV included. Guests should bring their own media devices. A HDMI compatible TV is provided. No air conditioning but high airflow due to fans, circular house and bluff location. Memory foam pad is available for use with futon or fold out. Monthly discount only Nov to Mar.

A Wise Getaway / Farm Cottage Near Keuka Lake
Welcome to 'A Wise Getaway' Amish-Built 800 Sq Ft Cottage on 50-Acre Farm – No Cleaning Fee! A peaceful retreat for couples, families & your four-legged friends Just 2 miles from Keuka Lake & minutes to the Village of Hammondsport, NY Minutes from wineries, breweries, NYS hunting land & Waneta / Lamoka Lakes ♿ Handicap accessible 🐾 $40 pet fee 🔥 Fire pit 📡 Wi-Fi 🍔 BBQ grill 📺 Premium DIRECTV + Sports Packages Top 5% rated Airbnb in region 20–30 mins to Watkins Glen, Penn Yan & Corning

All Seasons Base Camp - Finger Lakes
*King sized bed; Private Entrance; Keurig Coffee Machine; Roku TV; Mini Fridge; Microwave; Toaster; Walk to Main Street, restaurants, wineries, distillery and breweries* All Seasons Base Camp is perfect for a couple or 2 friends looking for a comfortable and convenient place to stay while visiting the Finger Lakes Region for hiking, biking, fishing, skiing, water falls chasing, and wine tasting! No A/C needed.stays cool in the Summer months due to the home being built into the side of a hill.

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.

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.

Modern, bright & calm 1 BR / 1 bath farm retreat
Let the calm, quiet beauty of New York’s Finger Lakes region renew you at this modern and bright on-farm escape right on the Seneca Lake Wine Trail. Enjoy our outdoor space and the comfort of our new building's private second floor which features natural lighting, a private entrance, self check-in, marble countertops, tile throughout, a custom bathroom, in-floor radiant heat, WiFi, no TV and a spacious deck overlooking Black Squirrel Farms, a black walnut growing and processing operation.

Whenland off grid tiny house with wood stove
Whenland is the name of this extraordinary 3 acre wooded property nestled in the hills of Naples, NY. Feel like roughing it, but don’t want to get too rough? Nestled back away from the road you'll find a fire pit, a small wooden handmade log bridge, repurposed material sculptures, and a wood stove heated tiny house from a repurposed trailer. This place has solar energy only, no running water and a composting toilet outhouse. Wine country, hiking, lakes, gorges, nature rich earth abound!

2nd Fl. Studio Walkable In town no cleaning fee
1870 Historic Victorian 2nd floor studio with separate kitchen. No smoking or vaping inside of the unit please. No parties. Guests need to climb deck stairs and inside staircase to access apartment. Steps from downtown, near wineries, breweries, restaurants. Locally owned family home with pets. Stove, microwave, blender, toaster, refrigerator, coffeemaker. Propane BBQ grill Queen, single day bed trundle underneath (all beds in the same room) Free wifi, Netflix, Roku tv, YouTube tv

Hillside Retreat Walking Distance to Downtown
Private spacious suite with separate entry and brand new bathroom. You will have the entire walkout lower level with a full bathroom including laundry. Beautiful queen bedroom set. Comfortable sectional with chaise ready for you to put your feet up and unwind. This has a pullout queen size bed for extra sleeping. Game table stocked with supplies. Coffee bar with all of the essentials including a mini fridge and microwave. You can even get your exercise in with using the treadmill.

Off Grid Bus at Bright Sky Farm
Unplug- and recharge- in our rustic converted school bus. Swim in the pond, meditate in the garden, pick raspberries and see some of the best night sky viewing around. Visit with the farm animals and tag along for chores if you want. This skoolie is far from the swanky, expensive ones you've seen on social media- this is a simple, rustic and very old bus that we were lucky enough to live in with our kids while we looked for our perfect farm, and now we're happy to share it with you!
Popular amenities for Penn Yan family-friendly rentals
Family-friendly home rentals with a hot tub

Peaceful Finger Lakes Studio

Comfort and Luxury- Keuka Lake Dream Property

Drift Away Hot Tub, Kayaks, Lakefront & Games

Bristol Retreat Cottage

Peppermint Cottage

The Lakeview Chalet: Cozy & Chic, Hot Tub, Games

Thyme Away!

Cozy cottage in the Heart of the Finger Lakes with
Family- and pet-friendly home rentals

Retreat @ Keuka Cabin

Cozy little 3 story cabin in the woods

Enjoy spectacular sunsets at The Chalet at Keuka!

The Old Whittier Library in Finger Lakes

Modern Colonial Walking Distance to Town & Outlet

Suite Dreams

Beautiful & quiet place. A true in-law house.

Private Year-round Lakefront on Seneca Wine Trail
Family-friendly home rentals with a pool

Hazlitt Winery Poolhouse

Villa Vino - Outstanding 4bd home w/Hot Tub & Pool

Fireplace, theater room, & fully equipped kitchen

Camp S’mores- Modern A-Frame with Pool

Charming Pittsford Home-Indoor Pool-4 bedrooms

Sky House- private sanctuary in the clouds

Luxury lakefront apartment - and a private pool!

Foster Hideaway - lake views, pool, hot tub.
When is the best time to visit Penn Yan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $193 SGD | $222 SGD | $278 SGD | $255 SGD | $265 SGD | $281 SGD | $323 SGD | $321 SGD | $300 SGD | $260 SGD | $260 SGD | $239 SGD |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 11°C | 5°C | 0°C |
Quick stats about holiday rentals that are family-friendly in Penn Yan

Total holiday rentals
Explore 40 holiday rentals in Penn Yan

Nightly prices starting at
Penn Yan holiday rentals start at $170 SGD per night before taxes and fees

Verified guest reviews
Over 2,350 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
40 of Penn Yan holiday rentals include wifi 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!
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- Cornell University
- Letchworth State Park
- Watkins Glen State Park
- Greek Peak Mountain Resort
- Chimney Bluffs State Park
- Sea Breeze Amusement Park
- The Strong National Museum of Play
- Bristol Mountain
- Taughannock Falls State Park
- Fair Haven Beach State Park
- Cayuga Lake State Park
- Stony Brook State Park
- Song Mountain Resort
- Watkins Glen International
- Keuka Lake State Park
- Cascadilla Gorge Trail
- Sciencenter
- High Falls
- Hunt Hollow Ski Club
- Three Brothers Wineries and Estates
- Keuka Spring Vineyards
- Fox Run Vineyards
- Standing Stone Vineyards
- Bet the Farm Winery




