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Holiday rentals in Penn Yan

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Top-rated holiday rentals in Penn Yan

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious bedroom features a large bed dressed with a floral quilt and numerous pillows. A wooden dresser with a mirror occupies one wall, while framed artwork adorns the other walls. A fan hangs from the ceiling, and a chair is positioned nearby.
Flat in Penn Yan
4.98 out of 5 average rating, 572 reviews

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

Top guest favourite
Chalet in Penn Yan
4.94 out of 5 average rating, 159 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
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
4.95 out of 5 average rating, 211 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
Cottage in Penn Yan
4.99 out of 5 average rating, 157 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, 106 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.

Top guest favourite
A charming boathouse is situated directly on the water, featuring a deck above the water and steps leading up to the main house. The exterior showcases natural wood tones and large windows, providing views of Seneca Lake from both levels.
Home in Penn Yan
4.99 out of 5 average rating, 271 reviews

Waterfront Escape in Seneca Lake Wine Country

A true refuge... peaceful, quiet and majestic. The house is right on the lake with gorgeous views of Seneca lake. Large windows overlook the lake from the living room and front bedroom. Single family detached home situated on a dead-end street limited to local traffic, this 2 bedroom, 1 1/2 bathroom year-round home will provide you with everything you need for your next getaway. The house is perfect for 2 couples or a family of four. Bonus room above the boathouse with a pull out sofa.

Top guest favourite
The kitchen features modern appliances, including a stainless steel fridge and oven, set against light-colored cabinetry and a mosaic backsplash. A spacious island with bar seating offers additional workspace. Natural light filters through large windows, illuminating the open layout.
Farm stay in Penn Yan
4.97 out of 5 average rating, 260 reviews

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 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.

Top guest favourite
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
4.97 out of 5 average rating, 135 reviews

The Tiny House on the Prairie - QKA

A little slice of calm and contentment in this rustic well appointed tiny house on wheels. IT'S GETAWAY TIME! Perfect for a couple. Stunning views of Keuka Lake. Fully furnished kitchen, deck with patio furniture & propane gas grill. Fire pit with adirondack chairs. Enjoy the symphony of the night time under the stars with s'mores. Great location to the wineries, breweries & restaurants. 3 minutes to Keuka Lake State Park. Almost everything we have is made in the USA.

Top guest favourite
Home in Penn Yan
4.97 out of 5 average rating, 100 reviews

Little red ranch house

Come check out our little red ranch in Penn Yan, NY. We are located in the heart of the Finger Lakes, the beautiful Keuka Lake is 1 1/2 miles away with a few public beach access points & parks! If you’re here for the wine you picked the right spot - Keuka Lake and Seneca Lake wineries are a short drive. We also are walking distance to the local shops on Main St. & many restaurants/bars. The Keuka Outlet Trail is right down the street and is great for walking and biking!

Top guest favourite
A charming guesthouse is set amidst a grassy landscape, framed by trees and shrubs. A gravel path leads to the entrance, with a sunset sky visible in the background. The structure features large windows and a clean, simple design.
Guest house in Penn Yan
4.97 out of 5 average rating, 150 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, 280 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
The exterior of the chalet showcases a newly remodeled black house with wooden shutters. A small deck is visible in front, surrounded by greenery. The roof is steeply pitched, and a garage is attached to one side, blending neatly with the overall design.
Home in Penn Yan
4.99 out of 5 average rating, 134 reviews

The Onyx Chalet by Keuka Lake

Keep it simple at this peaceful and centrally-located place. Our Chalet is a newly remodeled house on the edge of Penn Yan within sight of Keuka Lake. Seasonal lake views and beautiful sunset skies. A stones throw from Morgan Marine and Red Jacket park. Walking distance from restaurants and a public beach. Master bedroom on main floor with queen bed and access to bathroom. Two bedrooms upstairs and large bathroom. Comfortably sleeps 6-8 people.

Popular amenities for Penn Yan holiday rentals

When is the best time to visit Penn Yan?

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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Penn Yan?

    Four-legged friends are welcome in Penn Yan. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Penn Yan?

    Yes! Work meets play with ease at over 20 vacation rentals in Penn Yan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Penn Yan?

    Penn Yan has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Penn Yan?

    Experience the best of Penn Yan with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Penn Yan have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Penn Yan. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Penn Yan have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Penn Yan. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Penn Yan have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Penn Yan. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Penn Yan?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Penn Yan

  • Total holiday rentals

    Explore 60 holiday rentals in Penn Yan

  • Nightly prices starting at

    Penn Yan holiday rentals start at £60 per night before taxes and fees

  • Verified guest reviews

    Over 3,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Penn Yan holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Penn Yan rentals

  • 4.9 Average rating

    Penn Yan stays are highly rated by guests – averaging 4.9 out of 5!

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  2. United States
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  4. Yates County
  5. Penn Yan