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Top 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 £127
per night
3 May - 4 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 £193
per night
6 May - 7 May
Secluded & Clean Yurt, nestled in woods and gardens
Fridge, microwave, stovetop, dishwasher
Charming Hammondsport Home w/ Lake Views & Pool!
10.0 out of 10, Exceptional, (29)
"Cozy house with spacious property. Close to many wineries and breweries."
Charming Hammondsport Home w/ Lake Views & Pool!
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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
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.
10.0 out of 10, Exceptional, (220)
"Cute, well stocked cabin with a nice private yard."
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.
Fridge, microwave, stovetop, dishwasher
Charming Canandaigua Lake House w/ Deck & Views!
10.0 out of 10, Exceptional, (8)
"The property and location were great…the property manager was AWESOME! Very easy to communicate with! Our only complaint was no frying pans to cook with. We would highly recommend this property! Stunning views!"
Charming Canandaigua Lake House w/ Deck & Views!
Fridge, microwave, oven, stovetop
Lazy Loon Cottage is a Charming KEUKA LAKE cottage with amazing views!
10.0 out of 10, Exceptional, (76)
"This property was very clean and comfortable! The view from the deck was outstanding and we loved that it was very close to the lake. The location was great and was close to a lot of great wineries/breweries that we visited during our stay. I will say that I did make the mistake of not reading all the way through the amenities list and did not realize that the house did not come with towels/washcloths or bed sheets/pillowcases, so just make sure to bring those with you when staying here! Overall...
Lazy Loon Cottage is a Charming KEUKA LAKE cottage with amazing views!
Property grounds
Lakefront, dock & fireplace! Sunsets! Wineries & brewery nearby! SUPs+Kayaks!
10.0 out of 10, Exceptional, (9)
"Lovely house with great views of the lake."
Lakefront, dock & fireplace! Sunsets! Wineries & brewery nearby! SUPs+Kayaks!
Terrace/patio
Wine Trail Dreams - 2 BR Cottage - Perfect location on the Seneca Wine Trail!
10.0 out of 10, Exceptional, (102)
"Everything was wonderful. Thank you, Gibbs family!"
Wine Trail Dreams - 2 BR Cottage - Perfect location on the Seneca Wine Trail!
Exterior
Log Cabin Retreat, Cayuga Wine Trail, Dogs Welcome, Open Year-round
10.0 out of 10, Exceptional, (217)
"We had a great 4 days staying in cabin A. The cabin was very nice and had everything you would ever need. We had our dog with us and this place is perfect for dog owners. Highly recommended with plenty of parks and other places to see and visit."
Log Cabin Retreat, Cayuga Wine Trail, Dogs Welcome, Open Year-round
Fridge, microwave, oven, stovetop
Escape to Nature's Paradise: Your Private Retreat on 4 Acres in Wine Country
10.0 out of 10, Exceptional, (15)
"Lovely modern cozy home. Peacefull surroundings with easy access to finger lakes attractions. Professional caring hosts. We had 6 inches of snow overnight. Shanisha sent out their plow guy to clear the path just incase we wanted to venture out on that day. Will for visit and stay here again. Thank you, Dean"
Escape to Nature's Paradise: Your Private Retreat on 4 Acres in Wine Country
Property grounds
Cozy new England style cottage Right on Wine and Beer Trail
9.8 out of 10, Exceptional, (233)
"Clouds mad the eclipse on April 8 less than hoped for, but still a wonder, but we had a great family weekend trip thanks to the lovely cottage hosted by Tim and Bonni. A beautiful clear sky Sunday let us enjoy the dock, and the views! We aren't fancy people, and the cottage was very homey, very clean, comfortable. We would love to come back sometime."
Cozy new England style cottage Right on Wine and Beer Trail
Pool
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
9.8 out of 10, Exceptional, (112)
"We had a great time relaxing by the fire pit. Everything we needed to keep a good fire going for multiple nights was provided. Close by to good breakfasts at Angels, and just a short drive to Watkins Glenn and other attractions by the lake."
The price is £122
per night
27 May - 28 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
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
Terrace/patio
WELCOME! WE ARE PET FRIENDLY.
9.8 out of 10, Exceptional, (230)
"This house is just enough off the beaten path. Quiet, and no neighbors. There is plenty of space inside. Fully stocked with cooking and eating utensils. The owner has provided books and games. The fireplace was the perfect touch, as we woke up to snow one morning. Not too far from all Keuka has to offer, but a wonderful place to kick up your feet and relax. I loved the added touch of the antiques for the decor!"
WELCOME! WE ARE PET FRIENDLY.
Exterior
The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK
9.6 out of 10, Exceptional, (27)
"We had a great stay. The place was staged so cute. Only downfall was we couldnt find the hot tub at first and the location of the hot tub was awkward. Maybe putting out bathrobes in the winter ?"
The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK
Dining
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
9.6 out of 10, Exceptional, (118)
"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 £165
per night
6 May - 7 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
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
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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.

Penn Yan Holiday Rental Travel Info

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) | Premium bedding, in-room safe, laptop workspace, blackout curtains
Best Western Plus Vineyard Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (1003)
"Location is great and staff is top notch "
The price is £109
per night
7 May - 8 May
Best Western Plus Vineyard Inn & Suites
Sports facility
Hampton Inn Penn Yan
2.5 star property
9.4 out of 10, Exceptional, (807)
"Our go to when we want to stay in wine town"
The price is £89
per night
27 May - 28 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.

Everything you need to know about Penn Yan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Penn Yan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Penn Yan holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Penn Yan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Penn Yan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Penn Yan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Penn Yan holiday rentals we have selected for you start as low as £122 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Penn Yan rentals

At Expedia, we put the best Penn Yan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Penn Yan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Penn Yan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Penn Yan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK: This highly rated holiday home rental in Penn Yan is located in a rural location, and has a fireplace, a private balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and 1 hot tub so that you can immerse yourself in your holiday. 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 Cozy Bungalow right on the Lake wine and brewery trail..

How many holiday rentals are there in Penn Yan?

With 130 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