Holiday houses in Penn Yan

4.97 out of 5 average rating, 516 reviews

Apartment in Penn Yan

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

Guest suite in Bloomfield

4.94 out of 5 average rating, 380 reviews

Farm House Suite 15 minutes from Canandaigua Lake

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.

4.92 out of 5 average rating, 183 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.

4.99 out of 5 average rating, 225 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.

4.95 out of 5 average rating, 181 reviews

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.

Guesthouse in Hammondsport

4.89 out of 5 average rating, 337 reviews

A Wise Getaway AirBnB

Simple Amish-Built Cottage on 50-Acre Farm near Keuka Lake 800 sq ft cozy, Pet-Friendly escape just 2 miles from Keuka Lake & minutes to Village of Hammondsport, NY & award winning wineries & breweries. Handicap accessible Includes Wi-Fi, fire pit, bbq grill Premium DIRECTV (HBO, Starz + Various Sports Packages) 5 mins to Waneta / Lamoka Lakes & NYS hunting land. 20-30 mins to Watkins Glen, Penn Yan & Corning. Not the Ritz—just peaceful country living Top 5% rated Airbnb in our region

4.98 out of 5 average rating, 126 reviews

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.

4.98 out of 5 average rating, 213 reviews

Farm stay in Penn Yan

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.

4.86 out of 5 average rating, 173 reviews

Tiny home in Penn Yan

Hollow Hills Tiny Home

Brand new double lofted Tiny Home on wheels located upon a private country hillside. Overlooking the hills of Keuka Lake, guests can enjoy radiant sunrises, knowing they are just minutes from the local wine trail/ breweries, Crispin Hill Wedding Venue, Apple/ Grape picking, the list goes on! While enjoying a cup of coffee, guests can take in a quiet and tranquil morning, all while being just a half mile from the Village of Penn Yan. Stay connected with our wifi, or just relax by the fire!

4.69 out of 5 average rating, 185 reviews

Apartment in Penn Yan

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

4.98 out of 5 average rating, 110 reviews

Bungalow in Penn Yan

Qka Lake Daze jr.

Newly renovated Keuka Lake bungalow. Full kitchen and tile bath and shower. Cottage has king size bed, full laundry common living area and small eat in space. Covered full front porch for relaxing and eating meals while enjoying listening to the waves. Beautiful flat beach frontage with your own dock and fire pit. Sit back and enjoy the lake breeze while laying in the hammock or leaning back in the adirondack chairs. Come explore all the attractions of the Finger Lakes.

4.92 out of 5 average rating, 233 reviews

Cabin in Penn Yan

Penn Yan/Keuka Lake/Wine Trail, Outlet Trail Cabin

2016 Cabin borders the Keuka Lake Outlet/Trail. The Keuka Lake Outlet is the waterway that runs from Keuka Lake to Seneca Lake. The Outlet trail is a 6+ mile walking/biking trail with great views, waterfalls, etc. Cabin has heat/A.C, microwave, refrigerator, coffee pot, USB charging outlets for cell phones. Outdoor cook grill and fire pits for campfires. If more sleeping capacity is needed let us know ahead and we can park our camper there for you (added fee)

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Other great holiday rentals in Penn Yan

4.97 out of 5 average rating, 36 reviews

Cozy Village of Penn Yan Home, Near Keuka Lake

McKaylaRating, 5 stars5 months ago

We stayed at Jeremiah’s place for a birthday and New Years Eve trip. The place was perfect for our group and my pup loved it too! It was very spacious and had everything we needed. Plenty of towels too which was a huge plus and the washer and dryer was great for a muddy mishap There’s so much to do in town and great options for eating and Amity for coffee is a must! There are a bunch of local parks I was able to take my dog too as well that he loved. We really enjoyed our time on Lake Keuka!

4.87 out of 5 average rating, 63 reviews

Funky Penn Yan Cottage

RachelRating, 5 stars3 weeks ago

Brennan was a super responsive and communicative host leading up to and during our trip. The AirBnB is exactly as pictured and comfortably fit our group of 5. The kitchen had everything we needed and we enjoyed all the care she put into making this place feel like home. Additionally, Penn Yan is a wonderful town to stay in when wine tasting in the fingerlakes. It is pretty much half way point between Keuka and Seneca so we were able to get everywhere we needed in a short time. I would absolutely stay here again and recommend that you do on your upcoming trip! :)

4.89 out of 5 average rating, 45 reviews

Country Cottage

ErinRating, 5 stars2 months ago

Lovely weekend getaway. Cozy stay inside and outside. Visited our favorite wineries. Nice quiet walks. Rained a lot but that didn’t matter with wood burning stove inside. His house offers everything to able to just bring yourself, clothes and food.

4.77 out of 5 average rating, 22 reviews

Loft in Penn Yan

118 Main Loft: Cozy Downtown Escape

KathyRating, 5 stars3 weeks ago

Great place if you’re looking for walkable restaurants and shopping. It was nice to be right in town!

5 out of 5 average rating, 20 reviews

Farm stay in Penn Yan

Barn Loft Living

NathanRating, 5 stars3 weeks ago

We’ve stayed many times at the fingerlakes and Kellils has definitely been our favorite spot so far. Kellil was super responsive to anything we asked or needed. The property was awesome, we got to walk the farm and see all of the animals apart of the petting zoo. She even let us see some new born piglets! Being within minutes from Seneca lake wine trails it’s a great place to stay and we will definitely come back.

5 out of 5 average rating, 15 reviews

Villa Rosita

PaulRating, 5 stars9 months ago

My girlfriend and I were in Penn Yan for a wedding. Paulina’s place was in a great location quick drive to downtown and the lake. We were only a single couple but there is plenty of room for two couples; the unit is overall spacious, two large bedrooms, 3/4 bath + additional 1/2 bath. Good value, I would recommend.

4.66 out of 5 average rating, 203 reviews

Cabin in Penn Yan

Hidden Gem in the Finger Lakes

PeytonRating, 5 stars3 weeks ago

Teresa’s cabin was a sweet rustic paradise! It was such a cozy place to rest during a hectic wedding weekend. It’s definitely nothing fancy, but it is in an awesome location in the woods and really, really close to downtown Penn Yan. Had no issues bringing our own linens, and we simply picked up bottled water from the grocery store for drinking since we didn’t like the taste of the well water. There were a couple of bugs and it was a bit dusty here and there, but it’s a rustic cabin in the middle of the woods! All in all, I would absolutely stay here again. Teresa was very responsive and a great host!