Photo by Matthew Jay

Penn Yan Holiday Rentals

April 2025

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May 2025

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Holiday Rentals in Penn Yan

Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI

9.8 out of 10, Exceptional, (225)
"We love this house, 3rd time here! So cozy and always provides fun time and leave us with great memories! We will definitely be back!"
Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI

Cozy Cabin With 165 Ft. Private Beach and wood-fired hot tub - ALL are welcome!

10.0 out of 10, Exceptional, (221)
"Perfect place to celebrate our 40 years of marriage. Bonus, I am from Syracuse, but moved to Pittsburgh in 1972. Amazing little property. The bald eagle visit the one morning was unreal!!!"
Cozy Cabin With 165 Ft. Private Beach and wood-fired hot tub - ALL are welcome!

Cozy All Season Bungalow right on the Lake wine and brewery trail.

9.6 out of 10, Exceptional, (25)
"Nice property for a couple. Would be tight with more than 2, but i believe they have another cabin nearby too. Great view of the lake. We went in the winter, so didn't use the patio or small beach firepit, but it looked nice."
The price is NZ$382
includes taxes & fees
3 Apr - 4 Apr
Cozy All Season Bungalow right on the Lake wine and brewery trail.

Cozy new England style cottage Right on Wine and Beer Trail

9.8 out of 10, Exceptional, (255)
"Nice quiet"
Cozy new England style cottage Right on Wine and Beer Trail

Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

9.8 out of 10, Exceptional, (129)
"The cabin was absolutely perfect! The hosts are very thoughtful, providing coffee, cups, towels and bedding along with other amenities to make you feel at home! Loved the seclusion but also close enough to activities in the area. I would highly recommended this place! I will definitely stay here again when in this area!enough"
The price is NZ$306
includes taxes & fees
30 Apr - 1 May
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

Keuka East: Spacious & Comfy

9.6 out of 10, Exceptional, (133)
"We had a great time and the property was exactly what we were looking for. Owners were great to deal with and communication was excellent. We would rent again from them again for sure!"
Keuka East: Spacious & Comfy

The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK

9.8 out of 10, Exceptional, (37)
"Beautifully decorated farm house with hot tub was the perfect place to relax after visiting the area state parks. We highly recommend this home. Thanks for an enjoyable stay!!"
The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK

It's A Wonderful Life -Main St Penn Yan-Hot Tub-Seneca/Keuka, Restored Victorian Home-Nightlife

9.0 out of 10, Wonderful, (26)
"Hot tub and fire pit were great. Had to get firewood though. No toilettes provided unlike other vrbos we have stayed at. Beds are truly high, but are very soft and comfortable. "
It's A Wonderful Life -Main St Penn Yan-Hot Tub-Seneca/Keuka, Restored Victorian Home-Nightlife

Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake

9.6 out of 10, Exceptional, (132)
"We stayed one night, & it met our needs for a place to sleepy& shower after a friends wine tasting. We hope to stay there again when in the area. Mary, & her family were friendly & helpful."
The price is NZ$359
includes taxes & fees
2 Apr - 3 Apr
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake

Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake

9.8 out of 10, Exceptional, (63)
"It is a great location rain or shine. The central living room is undersold online as we have had groups as big as 7 indoors all day due to rain without being on top of each other. Everything you need for your stay is there, and if it isn't Mary is able to help. Really a great little spot to relax and enjoy yourself. "
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake

Sunflower-Keuka/Seneca-Lake View-Hot Tub-Wine Trail-Pets, 13 Wooded Acres-7 min to Beach

9.4 out of 10, Exceptional, (88)
"This is our second trip to Sunflower Cottage and the location is perfect. Near wineries, markets and the lake, this charming cottage has turned into our go-to spot for a fall getaway!!"
Sunflower-Keuka/Seneca-Lake View-Hot Tub-Wine Trail-Pets, 13 Wooded Acres-7 min to Beach

The Vineyard House at Fox Run Vineyards: Seneca Lake Wine Dream Home

10.0 out of 10, Exceptional, (11)
"We could not have asked for a more beautiful home to spend the weekend at the lake to celebrate our daughter in law's birthday! "
The Vineyard House at Fox Run Vineyards: Seneca Lake Wine Dream Home

Lakefront gem with game room and dock - the house that almost floated away

9.4 out of 10, Exceptional, (54)
"The house was wonderful- spacious and very comfortable with gorgeous views. It had everything that we needed and was conveniently located to a variety of restaurants, town, and things to do.Was not pleased that everything was handled through vacasa(?) which took away from the personal touch aspect.Response to request was generic and checking out, I didn’t even realize that I was supposed to let them know (email read when I got home) til I was home - 6 hours later - so they’re cleaning team could...
Lakefront gem with game room and dock - the house that almost floated away

Pet Friendly Log Cabin

9.4 out of 10, Exceptional, (50)
"Its the cabin I've been searching for for years, Its very clean and the outside environment is very spacious. The outside bathroom was very clean. It does have solar powered lights but they dont last forever so bring lanterns, There is no running water so plan for that, There was evidence of mice so if that creeps you out then dont rent. Its very secluded so Animals are expected. Ive already rebooked. There was no coffee pot so i brought my own propane coffee pot because that porch was too...
The price is NZ$232
includes taxes & fees
9 Apr - 10 Apr
Pet Friendly Log Cabin

Family/Dog Friendly cottage on Seneca Lake @ Long Point Beach with awesome views

9.0 out of 10, Wonderful, (14)
"Central to wineries "
Family/Dog Friendly cottage on Seneca Lake @ Long Point Beach with awesome views

Stunning, Fully-Loaded Home with Private Hot Tub, Pool Table, and Dock

8.6 out of 10, Excellent, (38)
"The property has so many health and safety problems that it should not be rented to anyone else. The MOLD and MOUSE DROPPINGS throughout the home were indications of a lack of careful cleaning and was unsafe. Overall, the home was dirty, outdated, worn out and needed so many items fixed. This property will need the owners to seriously spend money to get it right. Do not be fooled by the online photos... sure, the location and view are great, but the home has so many issues that I do not ever...
Stunning, Fully-Loaded Home with Private Hot Tub, Pool Table, and Dock

Luxuriously Crafted Earthen FLX Cottage Retreat

10.0 out of 10, Exceptional, (58)
"Awesome cabin in the finger lakes. We stayed a night in the winter and once we got the fireplace going it was toasty. Perfect spot to unwind. Would stay again!"
The price is NZ$455
includes taxes & fees
2 Apr - 3 Apr
Luxuriously Crafted Earthen FLX Cottage Retreat

Croft Cove: laid back home on Lamoka Lake with private lakefront

9.6 out of 10, Exceptional, (33)
"This house is such a gem. From the comfort of the beds to the view of the lake, everything was just wonderful. I would love to stay here again."
Croft Cove: laid back home on Lamoka Lake with private lakefront

Charming Canandaigua Lake House w/ Deck & Views!

10.0 out of 10, Exceptional, (21)
"Simple, clean and wonderful spot for a winter weekend getaway."
Charming Canandaigua Lake House w/ Deck & Views!

APRIL 11% Discount - Seneca Lake spacious 5-bedroom chalet JULY DATES NOW OPEN

9.6 out of 10, Exceptional, (151)
"Lovely location close to many wineries and an easy drive to Watkins Glen or Ithaca. Plenty of beds, seating and a large kitchen. Enjoyed the fire pit. We had two issues (water and plumbing) which were inconvenient for us, but Paul was easy to communicate with and quick to address them. "
APRIL 11% Discount - Seneca Lake spacious 5-bedroom chalet JULY DATES NOW OPEN
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.
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Other types of properties in Penn Yan you may be interested in

Hampton Inn Penn Yan

2.5 star property
9.4 out of 10, Exceptional, (1013)
"Very nice stay!"
The price is NZ$163
includes taxes & fees
20 Apr - 21 Apr
Hampton Inn Penn Yan

Best Western Plus Vineyard Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (1061)
"Rooms and staff were amazing but the breakfast was lacking."
The price is NZ$171
includes taxes & fees
7 Apr - 8 Apr
Best Western Plus Vineyard Inn & Suites

Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI

9.8 out of 10, Exceptional, (225)
"We love this house, 3rd time here! So cozy and always provides fun time and leave us with great memories! We will definitely be back!"
Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI
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.

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?

Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI: This highly rated holiday home rental in Penn Yan is located on a lake, and has a fireplace, a 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. You and your friends and family can relax into your holiday with amenities such as a selection of games. Other favourite homes for rent in Penn Yan are Cozy Cabin With 165 Ft. Private Beach and wood-fired hot tub - ALL are welcome! and Cozy All Season Bungalow right on the Lake wine and brewery trail..

How many holiday rentals are there in Penn Yan?

With 142 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.