Vacation rentals in Penn Yan, NY

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Penn Yan, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Penn Yan, NY

Top-Rated Vacation Rentals near the City Center in Penn Yan, NY

These downtown Penn Yan, NY vacation rentals put you near top restaurants, sights, and transit. Enjoy the heart of the city action.

Modern Studio - Main St Penn Yan - Penn Yan, NY
9.9 25 reviews

Modern Studio - Main St Penn Yan

apartment, Penn Yan
This Main Street studio apartment in downtown Penn Yan offers easy walking access to shops, restaurants, bars, kayak rentals, and a cafe.
The newly renovated unit, sleeping two, features a full kitchen with fridge, freezer, and microwave, plus WiFi, a washer/dryer, and a smart TV; guests can also enjoy numerous books and board games.
Sheridan House-studio:upscale Apartment On Main St - Penn Yan, NY
9.9 104 reviews

Sheridan House-studio:upscale Apartment On Main St

apartment, Penn Yan
This Penn Yan studio apartment, located in the 19th-century commercial district on Main Street, is steps from Amity Coffee Co. and the Burnt Rose wine bar.
The renovated unit features a king-size bed, full kitchen with dishwasher, in-unit washer/dryer, a bathroom with tub/shower, and accommodates two guests; EV charging is available at the nearby Penn Yan Public Library.
Sheridan House-studio:upscale Apartment On Main St - Penn Yan, NY
10 24 reviews

Sheridan House-studio:upscale Apartment On Main St

studio, Penn Yan
This studio apartment is located in Penn Yan's historic 19th-century commercial district, a short walk from the town library and within easy reach of Keuka Lake and Keuka Lake State Park. Guests consistently rate this studio as excellent, highlighting its convenient location and comfortable amenities. The 430-square-foot studio comfortably sleeps two guests and features an open layout with a well-equipped kitchen. Amenities include a full-size washer and dryer, a dishwasher, central air conditioning, and parking, making this studio a great choice for travelers seeking a convenient and comfortable stay in Penn Yan.
Steps To Downtown Penn Yan, Pet Friendly 2br - Penn Yan, NY
9.8 12 reviews

Steps To Downtown Penn Yan, Pet Friendly 2br

apartment, Penn Yan
This 2-bedroom apartment offers a prime downtown Penn Yan location, providing walkable access to restaurants, shops, and the outlet trail, and is housed in a unique historical building formerly serving as the local jail.
This lodging accommodates up to 6 guests with a pull-out couch, features a fully stocked kitchen and outdoor patio space, and serves as an ideal base for exploring the Finger Lakes region.

Best Penn Yan, NY vacation rentals with air conditioning

Lady Of The Lakes Suites 3: Vineyard Retreat - Penn Yan, NY
No reviews

Lady Of The Lakes Suites 3: Vineyard Retreat

apartment, Keuka Park
This apartment offers a prime lakefront location on Keuka Lake, situated on its northwest tip, providing convenient access to local wineries and hiking trails.
This "Vineyard Retreat" themed suite accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, internet, a private covered porch with a grill, and access to shared beach areas with a dock and firepit.
Waterfront Memories Begin At Deckside On Keuka! - Penn Yan, NY
No reviews

Waterfront Memories Begin At Deckside On Keuka!

apartment, Keuka Park
This spacious lakefront vacation home in Dundee offers direct access to Keuka Lake, just a short drive from Penn Yan and the Keuka Lake Wine Trail, with Ravines Wine Cellars and McGregor Vineyard nearby.
This 2780 square foot house accommodates up to 12 guests with 5 bedrooms and 4 bathrooms, featuring a private dock, lakeside firepit, expansive deck with lake views, and multiple gathering spaces including a second-floor living room.
The Roastery Loft - Penn Yan, NY
9.9 38 reviews

The Roastery Loft

apartment, Penn Yan
This fully renovated one-bedroom, one-bathroom urban loft is centrally located in Penn Yan's historic downtown, providing immediate proximity to the Keuka Outlet Trail, dining, wineries, breweries, lake access, and boutiques.
This apartment accommodates two guests and features air conditioning, internet, and a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher, offering a comfortable base for exploring the Finger Lakes region.
Huge Covered Porch On Lake-kayaks/bikes/air Hockey - Penn Yan, NY
9.9 165 reviews

Huge Covered Porch On Lake-kayaks/bikes/air Hockey

chalet, Penn Yan
This charming chalet sits just off Keuka Lake, a short drive from Penn Yan's downtown area, with the Arts Center of Yates County and Oliver House Museum nearby. Guests consistently rate the chalet excellent for location, cleanliness, and overall experience. The chalet offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. You'll enjoy a fully equipped kitchen, air conditioning, a private garden, and direct lakefront access for swimming, boating, and fishing.

Frequently Asked Questions about vacation rentals in Penn Yan, NY

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Best Vacation Rentals with Balconies in Penn Yan, NY

Enjoy a Penn Yan, NY vacation rental with a balcony and stunning city skyline views for a truly memorable stay.

Lake Shore Lodge: Spacious Keuka Lake Retreat! - Penn Yan, NY
9.6 4 reviews

Lake Shore Lodge: Spacious Keuka Lake Retreat!

apartment, Keuka Park
Lake Shore Lodge, a spacious Keuka Lake waterfront house in Penn Yan, offers stunning sunrise views and is a short drive from local wineries like Yates Cellars and Bristol Mountain ski resort (40 minutes).
This 5,010-square-foot vacation home boasts five bedrooms, four bathrooms, a sleeping loft, two kitchens, a game room with ping pong, and accommodates up to sixteen guests, plus seasonal access to a lakeside guest house.
New Build Keuka Lakefront | Sleeps 16 | Dock/kayak - Penn Yan, NY
8.0 1 review

New Build Keuka Lakefront | Sleeps 16 | Dock/kayak

apartment, Keuka Park
This lakeside retreat in the Town of Jerusalem offers direct access to Keuka Lake with a private dock for two boats, and is a short walk to swimming and fishing, with the Oliver House Museum, Narcissa Prentiss House, Hunt Country Vineyards, and Prejean Winery nearby.
This 3-bedroom, 4-bathroom apartment accommodates up to 16 guests and features modern comforts, air conditioning, internet, a fully-equipped kitchen with a fridge, microwave, and dishwasher, and a terrace or balcony with scenic lake views.
Restored 1850's Farmhouse - Classic Red Barn W Hot Tub - Seneca & Keuka Wine Trails - Pets Ok - Penn Yan, NY
9.0 2 reviews

Restored 1850's Farmhouse - Classic Red Barn W Hot Tub - Seneca & Keuka Wine Trails - Pets Ok

house, Penn Yan
This restored 1850s farmhouse, located 23 miles from the Glenn H. Curtiss Museum in Penn Yan, offers proximity to the Seneca and Keuka Wine Trails.
This pet-friendly vacation home spans 2500 square feet, featuring 4 bedrooms and 2 bathrooms to accommodate up to 15 guests, complete with a hot tub, terrace, garden, and free private parking.
Stunning Lakefront Family Friendly Getaway - Penn Yan, NY
9.8 57 reviews

Stunning Lakefront Family Friendly Getaway

apartment, Penn Yan
This lakefront vacation home is located in Penn Yan, just minutes from downtown, offering easy access to groceries, shopping, and Seneca Farms Ice Cream. The property is rated excellent by previous guests. This spacious home features 4 bedrooms, 4 bathrooms, and can accommodate up to 14 guests. The home offers a variety of amenities, including a private beach, a dock, kayaks, paddle boards, a fire pit, a playground, and a game room.

Top Vacation Rentals for Families in Penn Yan, NY

These kid-friendly vacation rentals in Penn Yan, NY keep you close to top city attractions for a stress-free family vacation.

Beautiful Retreat W/amazing Views-kayak&canoe! Lakefront! Free Wifi - Penn Yan, NY
9.6 261 reviews

Beautiful Retreat W/amazing Views-kayak&canoe! Lakefront! Free Wifi

apartment, Keuka Park
This four-bedroom, two-bathroom Adirondack log home rental in Penn Yan, on Keuka Lake, boasts over an acre of private wooded property with 115 feet of shoreline and direct lake access, conveniently located near Penn Yan's attractions including wineries and the Keuka Lake Outlet Trail.
The 8-guest home features two decks with lake views, a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, and a spacious living area, perfect for enjoying water activities like jet skiing and kayaking or exploring nearby hiking and cycling trails.
Morning Dove - Hidden Brookside Cottage In The Woods - Hot Tub - Fire Pit - Pet-friendly - Seneca & Keuka Wine Trails - Penn Yan, NY
9.5 2 reviews

Morning Dove - Hidden Brookside Cottage In The Woods - Hot Tub - Fire Pit - Pet-friendly - Seneca & Keuka Wine Trails

house, Keuka Park
This secluded 1400 sq ft vacation home in Keuka Park is situated in the woods with brookside setting, 30 miles from Sonnenberg Gardens Mansion State Historic Park and 20 miles from Glenn H. Curtiss Museum, offering proximity to the Seneca & Keuka Wine Trails.
This family-friendly, pet-friendly cottage accommodates up to 15 guests with 3 bedrooms and 2 bathrooms, featuring a full kitchen, WiFi, air conditioning, a jacuzzi, terrace, garden, and on-site parking, with access to a hot tub and fire pit for relaxation and outdoor activities like hiking and skiing nearby.
Just Us - Private Waterfront Home On Seneca Lake. Dog Friendly! - Penn Yan, NY
10 13 reviews

Just Us - Private Waterfront Home On Seneca Lake. Dog Friendly!

apartment, Dundee
This Dundee waterfront vacation home, near Fruit Yard Winery and within six miles of Starkey's Lookout and Glenora Wine Cellars, offers scenic views.
This 2,000-square-foot property boasts three bedrooms, two bathrooms, sleeps eight guests, and includes a swimming pool, terrace, and modern amenities such as a Smart TV and dishwasher.
Victorian Home In Penn Yan ~ 1 Mi To Keuka Lake! - Penn Yan, NY
9.8 28 reviews

Victorian Home In Penn Yan ~ 1 Mi To Keuka Lake!

apartment, Penn Yan
This 4-bedroom Victorian house is located steps from Main Street in Penn Yan, providing easy access to Keuka Lake and the Seneca Lake Wine Trail.
This 2520 square foot dwelling accommodates up to 8 guests with 3 king bedrooms, a full kitchen, a bar room with an arcade table, and a fenced backyard with a fire pit.

Best Penn Yan, NY vacation rentals with parking

The Loft: Downtown Loft Apartment - Penn Yan, NY
10 18 reviews

The Loft: Downtown Loft Apartment

apartment, Penn Yan
Sampson House: 3 Bedroom Town Home, Close To Shops - Penn Yan, NY
9.8 33 reviews

Sampson House: 3 Bedroom Town Home, Close To Shops

apartment, Penn Yan
Lady Of The Lakes Suites 3: Vineyard Retreat - Penn Yan, NY
8.0 1 review

Lady Of The Lakes Suites 3: Vineyard Retreat

apartment, Keuka Park
Grand Luxury Escape In The Heart Of Finger Lakes Wine Country - Penn Yan, NY
9.4 68 reviews

Grand Luxury Escape In The Heart Of Finger Lakes Wine Country

apartment, Dresden

Compare Luxury Vacation Rentals in Penn Yan, NY

Elevate your travel experience with a luxury rental in Penn Yan, NY, where high-end design meets a prime location.

Wine Lovers Retreat.  Agriturismo - Penn Yan, NY
9.8 46 reviews

Wine Lovers Retreat. Agriturismo

house, Keuka Park

Our Favorite Pet-Friendly Vacation Rentals in Penn Yan, NY

Experience a pet-friendly stay in Penn Yan, NY with vacation rentals located steps away from city dog parks and walking trails.

Unique Finger Lakes Converted Horse Barn W/ Patio! - Penn Yan, NY
10 7 reviews

Unique Finger Lakes Converted Horse Barn W/ Patio!

apartment, Gorham
Modern Colonial Walking Distance To Town & Outlet - Penn Yan, NY
9.9 123 reviews

Modern Colonial Walking Distance To Town & Outlet

apartment, Penn Yan
Restored Farmhouse With Hot-tub In Penn Yan, New York - Penn Yan, NY
No reviews

Restored Farmhouse With Hot-tub In Penn Yan, New York

house, Penn Yan
Blue Moon - Pet Friendly! - Off Grid - Romantic - Wine Trail Cabin - 4 Seasons - Penn Yan, NY
9.6 14 reviews

Blue Moon - Pet Friendly! - Off Grid - Romantic - Wine Trail Cabin - 4 Seasons

cabin, Prattsburgh

Explore Vacation Rentals with a Pool in Penn Yan, NY

A vacation rental with a pool in Penn Yan, NY makes it easy to fit in a proper swim right in the heart of the city.

Live The Lifestyle, Stunning Lake House In The Heart Of Wine Country! - Penn Yan, NY
10 5 reviews

Live The Lifestyle, Stunning Lake House In The Heart Of Wine Country!

apartment, Keuka Park
House Of Vines: Walkable Penn Yan Retreat. Kayaks And Indoor Pool Access - Penn Yan, NY
8.8 11 reviews

House Of Vines: Walkable Penn Yan Retreat. Kayaks And Indoor Pool Access

apartment, Penn Yan
Relaxing Lakeview Retreat! Pool, Hot Tub, Firepit, Gameroom Perfect For Groups, - Penn Yan, NY
10 29 reviews

Relaxing Lakeview Retreat! Pool, Hot Tub, Firepit, Gameroom Perfect For Groups,

apartment, Penn Yan

Search Vacation Rentals with Jacuzzi in Penn Yan, NY

These Penn Yan, NY city rentals feature private hot tubs, providing the perfect sanctuary after a day of urban exploration.

Keuka Vista - Penn Yan, NY
9.4 67 reviews

Keuka Vista

house, Penn Yan
The Farmhouse-seneca/keuka-hottub-winetrail-1850s Farmhouse, Classic Red Barn-big Rooms-pets Ok - Penn Yan, NY
9.6 54 reviews

The Farmhouse-seneca/keuka-hottub-winetrail-1850s Farmhouse, Classic Red Barn-big Rooms-pets Ok

apartment, Penn Yan
Crooked Lake Lodge: Adirondack-style Lodge On Keuka Lake! - Penn Yan, NY
9.8 6 reviews

Crooked Lake Lodge: Adirondack-style Lodge On Keuka Lake!

apartment, Keuka Park
At The Lake - 4 Bedroom, 3.5 Bath Contemporary - Penn Yan, NY
9.6 20 reviews

At The Lake - 4 Bedroom, 3.5 Bath Contemporary

cottage, Penn Yan
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