Family-friendly vacation rentals in Penn Yan

4.94 out of 5 average rating, 167 reviews

Chalet in Penn Yan

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

KitchenIndoor spacesHiking

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.

4.99 out of 5 average rating, 255 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.

KitchenFamilyAccess

4.96 out of 5 average rating, 227 reviews

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

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.

KitchenIndoor spacesValue

4.99 out of 5 average rating, 172 reviews

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

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.

KitchenFamilyGetting around

4.91 out of 5 average rating, 107 reviews

A serene lakeside view features soft clouds illuminated by warm sunset hues, reflecting on the calm water. Docks with boats are visible along the shoreline, framed by lush greenery and distant hills, creating a tranquil atmosphere.

Cottage in Penn Yan

Enjoy spectacular sunsets at The Chalet at Keuka!

The Chalet at Keuka is a lake lover's dream! Right on the water, you can enjoy panoramic views and beautiful sunsets on the spacious deck, or in one of two Florida rooms! You're in the heart of Finger Lakes, and a short drive from wineries, breweries, restaurants and parks. We allow up to two small breed dogs (up to 10 lbs), or one large breed dog. A couple of things to note: There are stairs leading to, and inside the cottage. Also, for guests over 6' 2", a few of the doorways are low.

Indoor spacesKitchenHiking

4.92 out of 5 average rating, 115 reviews

Home in Keuka Park

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.

KitchenFamilyTV

4.83 out of 5 average rating, 204 reviews

Retreat w/ panoramic lake views on wine trail!

Gather your crew & unwind at this peaceful, centrally located retreat - perfect for wine weekends, brewery tours & cozy nights in. With equal-sized bedrooms, a clean, stocked kitchen & a spacious deck made for group hangs, it has everything you need! ⭐ "Perfect home base for our wine trip - equal rooms, plenty of space, and so peaceful after a full day out!" ✓ Centrally located for wine & brewery hopping ✓ Equal-sized rooms & open group-friendly layout ✓ Deck for coffee, cocktails

FamilyIndoor spacesBiking

An outdoor deck is shown with a wooden frame, featuring a glass-top table surrounded by six beige chairs. The scenic view of lush greenery and distant hills is visible in the background under a clear blue sky.

4.96 out of 5 average rating, 220 reviews

Guyanoga Getaway ~Peaceful~ 5 min. to Keuka Lake

Nature lovers! Ideal vacation home for a small family, couples getaway or girls/guys weekend. Nestled in the woods, this secluded cabin-like ranch home has a beautiful view of the Guyanoga Valley. Located only 2 miles from Keuka Lake State Park, and a short drive to Penn Yan, this 3-bedroom has all of the comforts of home. Enjoy a cup of coffee on the deck. Minutes away from the lake; breathtaking scenery, wineries and craft breweries. You'll find small-town hospitality in Yates County.

Indoor spacesFamilyBeach

4.97 out of 5 average rating, 138 reviews

Apartment in Penn Yan

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.

FamilyKitchenBeach

4.98 out of 5 average rating, 176 reviews

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

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!

FamilyKitchenCleanliness

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.

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.

KitchenIndoor spacesCleanliness

4.98 out of 5 average rating, 108 reviews

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

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!

Indoor spacesKitchenDecor

Popular amenities for Penn Yan family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 100 reviews

Home in Hammondsport

Modern Lakeside Villa with Pool and Hot Tub

KitchenFamilyAccess

4.94 out of 5 average rating, 308 reviews

Home in Geneva

Lakefront House: Hot Tub, Kayaks & Fire Pit

Indoor spacesFamilyBiking

4.98 out of 5 average rating, 160 reviews

A view of a lakefront property illustrating a well-maintained yard with green grass and a dock extending into clear water. An American flag gently flutters near the house, while several outdoor chairs and loungers are arranged for relaxation. Lush trees form a backdrop against a clear sky.

Home in Dundee

Private Waterfront Home Wine Trail Hot Tub Dock

FamilyKitchenGetting around

4.97 out of 5 average rating, 126 reviews

A clear stream flows over smooth stones, with sunlight filtering through trees in the background. The tranquil water glistens as it meanders past a stone-lined bank, adjacent to a fenced area that leads to a cottage structure. The natural setting offers a serene ambiance.

Home in Dundee

Malthouse

Indoor spacesFamilyNearby

4.95 out of 5 average rating, 382 reviews

A living room features a blue sofa adorned with decorative pillows, positioned across from a rustic wooden coffee table on a woven rug. A stone fireplace complements the space, while large windows provide a view of Seneca Lake and access to the expansive deck.

Cottage in Geneva

Seneca Sunsets: private lakefront, dock, hot tub

KitchenIndoor spacesOutdoor spaces

4.94 out of 5 average rating, 101 reviews

Home in Geneva

New Hot tub! Luxury Lakefront Views-Retreat

FamilyIndoor spacesLayout

4.85 out of 5 average rating, 189 reviews

A two-story cottage is nestled against the shore, surrounded by trees. A wooden dock leads to the water, where kayaks are visible. Several outdoor seating areas, including Adirondack chairs, are positioned on the lawn, providing views of the lake. An American flag proudly waves nearby.

Cottage in Branchport

Keuka Lakefront House on West Side with Hot Tub

Indoor spacesKitchenWifi

5.0 out of 5 average rating, 116 reviews

A spacious living area features a natural stone fireplace, surrounded by comfortable seating including a dark blue armchair and a light grey sofa. Large windows bring in natural light, and artwork adorns the wooden walls, enhancing the cabin's inviting ambiance.

Home in Canandaigua

Finger Lakes Hilltop Chalet Relax, Unwind & Renew

FamilyKitchenCleanliness

Family- and pet-friendly home rentals

A cozy bedroom is highlighted by a spacious bed topped with a patterned quilt. A small table and chair set is positioned nearby, complemented by a wall-mounted flat-screen TV. Soft lighting is provided by a window partially covered by a dark shade.

4.95 out of 5 average rating, 126 reviews

Modern Colonial Walking Distance to Town & Outlet

FamilyKitchenGrill

A two-story farmhouse is showcased with a well-maintained exterior featuring white siding and decorative shutters. A spacious deck with seating options overlooks a grassy yard, bordered by mature trees and fields beyond, providing an inviting outdoor space.

4.86 out of 5 average rating, 199 reviews

The Farmhouse next to Abandon Brewing Company

FamilyIndoor spacesHospitality

4.97 out of 5 average rating, 262 reviews

A serene lake view is framed by window panes, showcasing a colorful sunset reflected on the water. Outdoor seating is visible on the deck, with potted plants adding a touch of greenery. The atmosphere appears peaceful and inviting.

Cottage in Penn Yan

On Lake, Stunning Views, Sunrises, Pet Friendly!

KitchenFamilyNearby

A charming red ranch home is surrounded by colorful autumn foliage. A covered porch with seating is visible at the front, while leaves cover the ground. The residence features a metal roof and a well-maintained stone border, creating an inviting entrance.

4.97 out of 5 average rating, 105 reviews

Little Red Ranch House

Indoor spacesFamilyParks

Superhost

Yurt in Penn Yan

Pet Friendly Keuka Yurt

FamilyIndoor spacesTV

4.82 out of 5 average rating, 317 reviews

4.97 out of 5 average rating, 146 reviews

A tiny house on wheels is set against a backdrop of autumn-colored foliage and Keuka Lake. Two tall trees provide shade, while a glimpse of the water can be seen in the distance. Fallen leaves blanket the grassy area, enhancing the natural setting.

Tiny home in Keuka Park

The Tiny House on the Prairie - QKA

Indoor spacesKitchenQuiet

4.97 out of 5 average rating, 228 reviews

The entrance of a historic home showcases a vibrant pink front door framed by white columns. Lush green plants flank the entryway, providing a welcoming appearance. A well-maintained lawn is visible in front, illuminated by natural light filtering through the trees.

Home in Geneva

Vintage Vineyard Cottage: Cozy Getaway, King Beds

FamilyKitchenComfort

4.87 out of 5 average rating, 626 reviews

A charming log cabin with a blue metal roof is situated amid lush greenery. The wooden exterior features multiple windows and a welcoming front door, complemented by a pathway lined with grass. Two chairs can be seen near the entrance, offering a place to relax.

Cabin in Naples

Hi-Tor Hideaway. The Cure for Cabin Fever.

Indoor spacesFamilyPets

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 230 reviews

Guesthouse in Burdett

Kline's Cottage

FamilyIndoor spacesBeach

4.89 out of 5 average rating, 148 reviews

A welcoming seating area is presented with two soft blue armchairs positioned on a decorative rug featuring floral patterns in shades of blue and cream. A small table with a lamp is situated between the chairs, and natural light enters through a large window overlooking a grill area.

Home in Pittsford

Charming Pittsford Home-Indoor Pool-4 bedrooms

KitchenIndoor spacesComfort

5.0 out of 5 average rating, 235 reviews

The exterior of a charming carriage house is highlighted, featuring a sloped roof and a well-maintained garden. A stone path leads to the entrance, and lush greenery surrounds the property, creating a welcoming atmosphere. Natural light softly illuminates the façade.

Guesthouse in Geneva

Seneca Carriage House

FamilyIndoor spacesGetting around

Apartment in Montour Falls

A well-appointed sleeping area features a queen-sized bed with a white comforter. A flat-screen television is mounted on the wall opposite the bed. Two bedside lamps provide soft lighting. A comfortable armchair sits in the corner, while a window allows natural light to enter.

Turner Park Suite

Indoor spacesFamilyCondition

4.99 out of 5 average rating, 118 reviews

4.88 out of 5 average rating, 147 reviews

A spacious property is set on a green lawn, bordered by trees with autumn foliage. The house features a sloping roof and a driveway leading towards the lake, which is visible in the background. The landscape showcases a serene view of the waters and surrounding hills.

Villa in Keuka Park

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

FamilyKitchenTV

Apartment in Seneca Falls

A spacious wooden deck is presented, featuring a circular above-ground pool surrounded by greenery. A shaded area is provided by a red umbrella over a dining table. Soft evening light filters through the trees, enhancing the serene outdoor space.

Luxury lakefront apartment - and a private pool!

KitchenFamilyShared spaces

5.0 out of 5 average rating, 147 reviews

5.0 out of 5 average rating, 112 reviews

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.

Home in Ithaca

Downtown Ithaca New Build – Award-Winning Stay

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