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Penn Yan Holiday Rentals

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Holiday Rentals in Penn Yan

Terrace/patio
Pine Grove Cabin
10.0 out of 10, Exceptional, (1)
"We just needed a place without light pollution near Lincoln hill farm, so we could go to a concert, then lay in the grass and see some meteors. Pretty great."
The price is NZ$255
includes taxes & fees
28 May - 29 May
Pine Grove Cabin
Property grounds
Secluded & Clean Yurt, nestled in woods and gardens
10.0 out of 10, Exceptional, (108)
"We had a great weekend staying in the property. The wood burner was great for a chilly early spring weekend, Elizabeth was very clear and accommodating in her communications making it very easy and everything was just great. My only regret is not booking the third night to stay for the Solar Eclipse and to get to explore the property further. We thoroughly enjoyed the area and the accommodations at the Yurt were perfect for my wife and I!"
The price is NZ$382
includes taxes & fees
28 May - 29 May
Secluded & Clean Yurt, nestled in woods and gardens
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.
10.0 out of 10, Exceptional, (223)
"Spent our 10 year wedding anniversary at this beautiful cozy cabin. Will be coming back and bringing the family."
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.
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Fridge, microwave, oven, stovetop
Secluded Oasis: Luxurious Retreat with Stunning Views
10.0 out of 10, Exceptional, (16)
"This property was a perfect getaway for my wife and I. Was a great spot to relax and detach from reality for a weekend. Everything was clean, the amenities were great, and Shanisha was available and easy to communicate with through the entire process. Will definitely consider booking again in the future!"
Secluded Oasis: Luxurious Retreat with Stunning Views
Interior
creek's edge
10.0 out of 10, Exceptional, (11)
"Charlie the owners was at the property very welcoming and nice .the property was amazing. Right on a river. The house was above incredible, you feel your at spa .he has everything you could ever want. The only down is the well water has a sulfur smell but he provides bottled water for cooking and cleaning .so no problem. Cool evening enjoyed a nice fire.the pictures on the site are exactly what it looks like. Dont think theres a picture of the bench by the river its a great place to set."
The price is NZ$279
includes taxes & fees
23 May - 24 May
creek's edge
Terrace/patio
Wine Trail Dreams - 2 BR Cottage - Perfect location on the Seneca Wine Trail!
10.0 out of 10, Exceptional, (105)
"This was our second time staying at this lovely house. The location was ideal, very clean and everything you needed for a delightful stay. Bonus was the brand new gas grill and coupon for the winery right next door! This will always be our go to spot for visiting Finger Lakes. P.S. even though we didn’t bring our pup this time, the fenced in back yard is ideal for your fur babies!"
Wine Trail Dreams - 2 BR Cottage - Perfect location on the Seneca Wine Trail!
Property grounds
STARWOOD - Romantic WINE TRAIL Cabin - Pet Friendly! 4 Season Rental
10.0 out of 10, Exceptional, (9)
"The amazing weekend getaway at your cabin and your gracious hospitality was exactly what we needed! We really appreciate all of the handy suggestions and recommendations - they filled our days with lots to do. The peace and quiet that this place has to offer was the perfect way to start and end each day. We will definitely make another trip out here in the future!"
STARWOOD - Romantic WINE TRAIL Cabin - Pet Friendly! 4 Season Rental
Exterior
Log Cabin Retreat, Cayuga Wine Trail, Dogs Welcome, Open Year-round
10.0 out of 10, Exceptional, (218)
"Very high end cabin. Clean and everything needed was there."
Log Cabin Retreat, Cayuga Wine Trail, Dogs Welcome, Open Year-round
Fridge, microwave, oven, stovetop
Lazy Loon Cottage is a Charming KEUKA LAKE cottage with amazing views!
10.0 out of 10, Exceptional, (77)
"Adam is a super host. This house is pristine and upscale. The kitchen has everything you need to make a gourmet meal. Nothing has been overlooked to make your stay wonderful. The master bedroom mattress is so comfortable you won’t want to get up. Then when you do, drinking coffee on the deck to watch the sun come up is amazing! The view of Keuka Lake is incredible. There’s a dock and shallow entrance into the lake making it ideal for all ages. Adam responded within minutes when we had a...
Lazy Loon Cottage is a Charming KEUKA LAKE cottage with amazing views!
Pool
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
9.8 out of 10, Exceptional, (113)
"Todd the owner is super nice and helpful to find nearby attractions. We checked in little early as well checked our early. Had a nice time relax and it was a kind of get away from the crowded and bustling city life."
The price is NZ$244
includes taxes & fees
28 May - 29 May
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
Property grounds
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake
9.8 out of 10, Exceptional, (59)
"Myself and all of my friends had a great time despite some spotty weather. The central living room being large enough to accommodate every one was essential to the weekend."
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake
Property grounds
Cozy new England style cottage Right on Wine and Beer Trail
9.8 out of 10, Exceptional, (236)
"Pre season stay was comfortable and quiet. The views of the exceptionally clean lake were breathtaking. An extremely relaxing getaway."
The price is NZ$695
includes taxes & fees
16 Jun - 17 Jun
Cozy new England style cottage Right on Wine and Beer Trail
Exterior
THE GRAPE ESCAPE - Wine Trail & Lake View Cabin - Pet Friendly! 4 Season Rental
9.8 out of 10, Exceptional, (34)
"The stay was wonderful! An extremely beautiful view, clean and serene space, and everything was provided for. Dave and his family were wonderful, and helped provide everything we could need. Even getting us out of the mud on the first night. Close to some of the best wineries and eats in the area, and a short drive to some very visually stunning parks beyond the lake itself. Their dog, Willy was an extra, added friend to us, and made our trip even more special. - Pete"
THE GRAPE ESCAPE - Wine Trail & Lake View Cabin - Pet Friendly! 4 Season Rental
Exterior
Secluded Dog-Friendly Studio w/Deck, Private Pond, Fireplace, Fast WiFi, Views
9.8 out of 10, Exceptional, (26)
"Had a great stay. Very peaceful"
Secluded Dog-Friendly Studio w/Deck, Private Pond, Fireplace, Fast WiFi, Views
Dining
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
9.6 out of 10, Exceptional, (119)
"Lovely little location close to state parks, Keuka lake and a bunch of wineries. Lost count on how many times I’ve stayed here. My girlfriend and I love the place."
The price is NZ$334
includes taxes & fees
28 May - 29 May
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
Property grounds
Anthony Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Big Deck, Recently Updated-New Dock-Pets OK
9.6 out of 10, Exceptional, (184)
"The location of the cabin was very convenient to a good amount of wineries. We visited 9 and didn’t have to drive any further than maybe 20 minutes, many of them were within a 5 minute drive. The cabin is on the lake, the hot tub is awesome! The cabin was cozy and made us feel right at home, even our dog was so relaxed there. it was staged beautifully when we arrived, and there were towels for the hot tub, plenty of bathroom towels, kitchen towels, and the kitchen had pots, pans, toaster,...
Anthony Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Big Deck, Recently Updated-New Dock-Pets OK
Exterior
The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK
9.6 out of 10, Exceptional, (28)
"Came here with friends, an infant, and a dog for a weekend in the Finger Lakes. The house has so much space, is charmingly decorated, and we all agreed the most comfortable beds we’ve ever experienced in a rental. Great location near multiple wineries. Owners had clear and prompt communication. Would absolutely rent again!"
The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK
Pool
Amazing Mills in the heart of the Finger Lakes
9.6 out of 10, Exceptional, (9)
"We had 6 adults, 1 infant, 1 child (5yo) and dogs stay and had plenty of space. The location was beautiful along the river and we enjoyed the short hikes to the falls."
Amazing Mills in the heart of the Finger Lakes
Property grounds
Gorgeous Farmhouse with lake view
9.6 out of 10, Exceptional, (20)
"Great location. Just a few negatives- coffee pot didn’t work well and directions for garbage were a little unclear. Otherwise everything we needed. Kids loved game room in garage and volleyball net. Nice fire pit. Front porch with view of lake was perfect for coffee and drinks"
Gorgeous Farmhouse with lake view
Beach front cottage with private beach and dock, amazing porch with sunset views
9.6 out of 10, Exceptional, (71)
"This trip was planned as a girls getaway to surprise our daughter (who has three sons) coming up from Florida for a long weekend. We had such a fun time we decided to make it a yearly tradition. The house held all 8 of us comfortably, in a beautiful setting right on Seneca Lake, offering a beautiful display of Gods creation from either of the two decks. LOTS of laughter & love!"
Beach front cottage with private beach and dock, amazing porch with sunset views
Don't see what you're looking for?
See all available properties in Penn Yan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Penn Yan you may be interested in

Property grounds
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake
9.8 out of 10, Exceptional, (59)
"Myself and all of my friends had a great time despite some spotty weather. The central living room being large enough to accommodate every one was essential to the weekend."
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake
Deluxe Suite, 1 King Bed with Sofa bed, Non Smoking (with Sofabed)
Best Western Plus Vineyard Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (1001)
"The staff was very pleasant and accommodating. The night before check out a family member had a medical emergency and needed to go to ER and they work with us to make check out extended because of hospitalization."
The price is NZ$199
includes taxes & fees
27 May - 28 May
Best Western Plus Vineyard Inn & Suites
Sports facility
Hampton Inn Penn Yan
2.5 star property
9.4 out of 10, Exceptional, (818)
"The hotel is at the end of Keuka Lake. We had a ground level room with our own patio. Great view and people. The staff was very accommodating. "
The price is NZ$202
includes taxes & fees
28 May - 29 May
Hampton Inn Penn Yan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Penn Yan holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Penn Yan. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Penn Yan. Seeing all the best attractions is bound to make you fall in love with Penn Yan. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Penn Yan short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Penn Yan?

Yes, there are holiday rentals close to the most popular sights in Penn Yan, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Penn Yan speak positively about the scenic lakeside and top-notch restaurants in this destination. While you're here, grab a bite or have a drink at the wineries.

What are some of the best holiday rentals that Penn Yan has to offer?

165+ private feet of direct lake frontage, with dock, grill, kayak: This highly rated holiday home rental in Penn Yan is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Other favourite homes for rent in Penn Yan are Anthony Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Big Deck, Recently Updated-New Dock-Pets OK and The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK.

How many holiday rentals are there in Penn Yan?

With 136 Expedia holiday rentals, you're guaranteed to find just the right place for your Penn Yan stay.

What’s there to see and do in Penn Yan?

Enjoy the outdoors at Keuka Lake Outlet Trail and Keuka Lake State Park, or simply take in cultural attractions like Arts Center of Yates County and Oliver House Museum. Other places in town to visit include The Windmill Farm & Craft Market and Fox Run Vineyards.

What’s a holiday rental in Penn Yan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Penn Yan. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.

Recent reviews of Penn Yan properties
Expedia verified reviews

The Lux Hotel & Conference Center, Ascend Hotel Collection

The Lux Hotel & Conference Center, Ascend Hotel Collection

5/5 Excellent
"All New, Great place"
A verified traveller stayed at The Lux Hotel & Conference Center, Ascend Hotel Collection
Posted 14 hours ago
The Lux Hotel & Conference Center, Ascend Hotel Collection