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 modern single-room cabin is nestled among trees, featuring large windows that offer natural light and views of the surrounding woods. A covered porch with seating invites relaxation, while a wooden railing adds to the cabin's rustic charm.
Cabin in Dundee
5 out of 5 average rating, 127 reviews

Timber View At Timber Trails

Escape to the countryside at the charming, “Timber View.” Surrounded by wineries & scenic beauty, this country retreat offers a peaceful getaway for those seeking to disconnect & rejuvenate. Wake up to the sounds of nature, enjoy your morning coffee on the porch, & spend your days exploring the Finger Lakes region with activities like hiking, visiting local farmers' markets, or simply enjoying the tranquility of rural life. In the evenings, gather around the fire pit for stories and stargazing.

Top guest favourite
A comfortable living area features a green sofa paired with a wooden rocking chair. A dark coffee table sits in front, with natural light illuminating the space through two windows. A dining table with four chairs is positioned nearby, creating a cozy gathering spot.
Flat in Penn Yan
4.98 out of 5 average rating, 561 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
A modern home with a circular shape is visible in the foreground, surrounded by lush green grass and trees. A gravel path leads up to the house, with expansive views of rolling hills and distant tree lines in the background under a clear blue sky.
Home in Penn Yan
4.92 out of 5 average rating, 211 reviews

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.

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, 206 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 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
4.97 out of 5 average rating, 250 reviews

On Lake, Stunning Views, Sunrises, Pet Friendly!

We are right on the lake! The view is amazing and the atmosphere is serene and relaxing. Conveniently located. The fully stocked cottage is comfortable and offers a homey feel - clean, updated. Gas fireplace offers additional warmth & ambiance. Fabulous deck with amazing views! Dock/beach area with fire pit. Master bedroom - watch the sunrise right from bed! Kitchen is fully stocked, seating for 6, laundry and two bathrooms. Plenty of parking and a lovely private yard. Linens included

Top guest favourite
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.
Home in Penn Yan
4.95 out of 5 average rating, 110 reviews

Modern Colonial Walking Distance to Town & Outlet

Perfect destination for families or friends seeking to experience the beauty of the Finger Lakes. Located steps from the Outlet Trail. This clean, and spacious home offers convenience, charm and comfort. Walking distance to downtown area restaurants. This is an ideal location to access both the Seneca and Keuka Lake wine trails. Two blocks from the public boat launch with plenty of off street parking for your boat and trailer. Barbecue on the grill or relax outside on the patio by the fire.

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, 152 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
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.
Home in Penn Yan
4.86 out of 5 average rating, 195 reviews

The Farmhouse next to Abandon Brewing Company

"The Farmhouse" is located in the heart of the Finger Lakes on the Keuka Lake Wine Trail. A restored 1800's farmhouse, it is close to the Village of Penn Yan, Keuka College, and Keuka Lake State Park and has amazing views overlooking Keuka Lake. The Farmhouse is on the same property as craft brewery and events venue, Abandon Brewing Company. Perfect for couples, families, groups, and furry friends (pets) who want to get away and enjoy the proximity to award winning wineries and breweries.

Top guest favourite
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.
Home in Penn Yan
4.97 out of 5 average rating, 210 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.

Top guest favourite
A wooden dock extends into the calm waters of Seneca Lake, featuring a ladder for easy access. Two chairs are positioned on the dock, inviting relaxation. The overcast sky reflects softly on the water's surface, creating a serene atmosphere.
Home in Penn Yan
4.99 out of 5 average rating, 265 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.

Superhost
The historic Victorian home features a light blue exterior with intricate wooden detailing. Large windows allow natural light to illuminate the interior, and a welcoming porch with decorative supports enhances the entryway. The roofline is gently sloped, adding to the charming character of the property.
Flat in Penn Yan
4.71 out of 5 average rating, 213 reviews

Budget Petfriendly 2nd fl Studio in PY walkable

1870 Historic Victorian 2nd floor studio with separate kitchen. No parties. 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

Top guest favourite
A tranquil lakeside view during fall showcases vibrant foliage, with trees in shades of orange, red, and yellow. Crisp leaves blanket the ground, while the calm water reflects the colorful landscape. A wooden dock is visible in the background, inviting relaxation by the lake.
Home in Keuka Park
4.94 out of 5 average rating, 284 reviews

Mutual Fun Keuka Memories

If you are going to just hang out, do it at this beautiful setting on Keuka Lake. Child-Friendly. Wonderful swimming area! Scenic drives around the vineyards. Spacious, comfortable home along a very quiet road. Cozy All-Season getaway! Enjoy your own private beach and dock. Swim/float/kayak in pristine waters. Walk along the lake. Stargaze. Campfires on the shore. Wintertime retreat. Brand new leather sofa, chair and ottoman. Nice, warm fireplace. Snuggle inside and let it snow!

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 house rentals in Penn Yan?

    Experience the best of Penn Yan with our house rentals, starting at about $100 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 House Rentals in Penn Yan?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, over 10 homes with a bbq area, 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 3,720 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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