Penn Yan holiday rentals

We found 917 holiday rentals — enter your dates for availability
Select from 158 homes, 58 cottages and other holiday rentals in Penn Yan to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Penn Yan

Showing deals for:18 Dec - 25 Dec

A guest's watercolor of the Lake House
Beach front
walk way to the front porch
Kitchen w/ view of back patio w/ firepit and grill
Exceptional
(117 reviews)

Idyllic Lakeside Victorian Farmhouse

Rock Stream

7% off
S$7,856
for 7 nights, 1 home
S$1,122 per night
includes taxes & fees
Idyllic Lakeside Victorian Farmhouse
Interior
Living area
Dining
Exterior
Exceptional
(13 reviews)

You’ve Found Paradise With this Spacious Log Cabin on Keuka Lake -

Branchport

8% off
S$11,143
for 7 nights, 1 cabin
S$1,592 per night
includes taxes & fees
You’ve Found Paradise With this Spacious Log Cabin on Keuka Lake -
Exterior
Interior
Dining
Terrace/patio
Exceptional
(10 reviews)

Finger Lakes Lodge overlooking Keuka Lake with 1st floor master bed & bath!

Pulteney

8% off
S$7,408
for 7 nights, 1 cabin
S$1,058 per night
includes taxes & fees
Finger Lakes Lodge overlooking Keuka Lake with 1st floor master bed & bath!
Living area
Outdoor dining
Exterior
Property grounds
Exceptional
(15 reviews)

Beautiful Seneca Lake Chalet with stunning lake and Pond views

Penn Yan

8% off
S$2,090
for 7 nights, 1 chalet
S$299 per night
includes taxes & fees
Beautiful Seneca Lake Chalet with stunning lake and Pond views
Fully stocked kitchen
Interior
Vinyl waterproof flooring in the kitchen.
Information binder on island to help guest enjoy their stay.
Exceptional
(151 reviews)

Newly Renovated Rustic Cabin w/WiFi in the Heart of the Finger Lakes

Branchport

8% off
S$949
for 7 nights, 1 cabin
S$136 per night
includes taxes & fees
Newly Renovated Rustic Cabin w/WiFi in the Heart of the Finger Lakes
second view of living room
Owners share 2 kayaks,peddle boat & row boat w/guests at 2 rental properties
view of cottage
one view of living room
Exceptional
(99 reviews)

Cozy Cottage with 45' Lake Frontage and Kayaks

Lodi

17% off
S$17,305
for 7 nights, 1 cottage
S$2,472 per night
includes taxes & fees
Cozy Cottage with 45' Lake Frontage and Kayaks
Interior
Property grounds
Outdoor dining
Private kitchen
Wonderful
(113 reviews)

Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch

Dundee

20% off
S$9,139
for 7 nights, 1 home
S$1,306 per night
includes taxes & fees
Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch
Outdoor spa tub
Sunset photo using iPhone on portrait mode.
New Kitchen Island
New landscaping w/ putting green and firepit added in 2025
Exceptional
(189 reviews)

VRFLX Seneca Lake Access | Walk to Beach

Hector

11% off
S$6,989
for 7 nights, 1 home
S$998 per night
includes taxes & fees
VRFLX Seneca Lake Access | Walk to Beach
Living area
Exterior
Property grounds
Private kitchen
Exceptional
(14 reviews)

Private, Rustic, Quiet, Quirky! Welcome to O'Cottage! 150 feet of lake frontage

Penn Yan

6% off
S$9,699
for 7 nights, 1 cottage
S$1,386 per night
includes taxes & fees
Private, Rustic, Quiet, Quirky! Welcome to O'Cottage! 150 feet of lake frontage
Downstairs bedroom
View from the living room
Overhead view of the living room
3 seasons sun room
Exceptional
(167 reviews)

Chalet overlooking Keuka Lake in the heart of Wine Country

Penn Yan

15% off
S$1,228
for 7 nights, 1 chalet
S$175 per night
includes taxes & fees
Chalet overlooking Keuka Lake in the heart of Wine Country
Private kitchen
We have outdoor seating (an umbrella is available for use) as well as a fire pit
Interior
Room
Wonderful
(14 reviews)

Cottage Retreat in the Heart of the Finger Lakes

Ovid

8% off
S$1,569
for 7 nights, 1 cottage
S$224 per night
includes taxes & fees
Cottage Retreat in the Heart of the Finger Lakes
Living area
Terrace/patio
Room
Interior
Exceptional
(12 reviews)

Bluebird Cabin - Brand New Cozy Log Cabin on 5-Wooded Acres / Pet-Friendly!

Dundee

8% off
S$2,193
for 7 nights, 1 cabin
S$313 per night
includes taxes & fees
Bluebird Cabin - Brand New Cozy Log Cabin on 5-Wooded Acres / Pet-Friendly!
Interior
Private pool area behind the house
Chef's kitchen with sliding doors to patio and window overlooking the playground
Campfires by sunset are an enjoyable family experience!
Exceptional
(95 reviews)

Lake House Open Year-Round! Summer Pool Fun & Fireplace Cozy Winter Retreat.

Ovid

8% off
S$5,457
for 7 nights, 1 home
S$780 per night
includes taxes & fees
Lake House Open Year-Round! Summer Pool Fun & Fireplace Cozy Winter Retreat.
Incredible sunrise view from one of the balconies
Newly remodeled kitchen 2022 with beautiful solid surface countertops
2nd floor: Master bedroom, walk-out balcony, master beds, chair, TV, fireplace
View from kitchen area overlooking living room, dining area and entryway.
Exceptional
(116 reviews)

Dreaming a View - Tranquil Retreat on Seneca Lake - Sleeps 12

Dresden

8% off
S$12,781
for 7 nights, 1 home
S$1,826 per night
includes taxes & fees
Dreaming a View - Tranquil Retreat on Seneca Lake - Sleeps 12
coat hooks in garage entry
Spacious living room
Enjoy the campfire
Large kitchen island
Exceptional
(200 reviews)

Friends And Family Farmhouse

Penn Yan

8% off
S$5,166
for 7 nights, 1 home
S$738 per night
includes taxes & fees
Friends And Family Farmhouse
bedroom down east facing
Southside porch
1.9 acres with dock, house view to cottage
den area
Exceptional
(5 reviews)

Charming 4-bedroom house with WiFi and AC in Branchport

Branchport

8% off
S$8,903
for 7 nights, 1 home
S$1,272 per night
includes taxes & fees
Charming 4-bedroom house with WiFi and AC in Branchport
Living area
Living area
Room
Living area
Exceptional
(467 reviews)

A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake

Penn Yan

8% off
S$2,292
for 7 nights, 1 cabin
S$327 per night
includes taxes & fees
A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake
Private kitchen
Property grounds
Beautiful sight at sunset!
Living area
Exceptional
(49 reviews)

Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23

Penn Yan

8% off
S$4,399
for 7 nights, 1 home
S$628 per night
includes taxes & fees
Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23
Living area
Outdoor dining
Private kitchen
Exterior
Exceptional
(193 reviews)

Serenity Zen House on Seneca Lake - Pet Friendly

Penn Yan

8% off
S$4,799
for 7 nights, 1 home
S$686 per night
includes taxes & fees
Serenity Zen House on Seneca Lake - Pet Friendly
Interior
Private kitchen
Living area
Room
Exceptional
(24 reviews)

The Ideal Vacation Location in the Heart of Wine Country

Penn Yan

8% off
S$2,376
for 7 nights, 1 home
S$339 per night
includes taxes & fees
The Ideal Vacation Location in the Heart of Wine Country
Dining
Living area
New couch and love seat
View from living room to sunroom
Exceptional
(127 reviews)

Immaculate Summer Home on Seneca Lake

Romulus

8% off
S$3,681
for 7 nights, 1 home
S$526 per night
includes taxes & fees
Immaculate Summer Home on Seneca Lake
Exterior
Serenity Aloft
Kitchen
Interior
Exceptional
(118 reviews)

Serenity on Seneca House - A Slice of Paradise

Penn Yan

8% off
S$5,514
for 7 nights, 1 home
S$788 per night
includes taxes & fees
Serenity on Seneca House - A Slice of Paradise
Dining
Living area
Room
Interior
Excellent
(12 reviews)

Fully furnished yr round home near Seneca Lake, on Wine trail, Family Friendly

Dresden

11% off
S$2,722
for 7 nights, 1 home
S$389 per night
includes taxes & fees
Fully furnished yr round home near Seneca Lake, on Wine trail, Family Friendly
Private kitchen
Outdoor dining
Room
Interior
Exceptional
(14 reviews)

Modern A-Frame near many wineries and activities: fire pit, King beds, & more!

Hector

8% off
S$5,157
for 7 nights, 1 home
S$737 per night
includes taxes & fees
Modern A-Frame near many wineries and activities: fire pit, King beds, & more!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The friendly area of Penn Yan awaits your stay

Enjoy the wineries and other features of Penn Yan. Revered for its lake, hiking and restaurants, this city is both welcoming and walkable. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Penn Yan

Are you searching for attractions to see in the city? Venture out of your holiday home and experience everything that Penn Yan has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Hermann J. Wiemer Vineyard (8.8 mi / 14.2 km)
  • Wagner Vineyards (11.7 mi / 18.9 km)
  • Three Brothers Wineries and Estates (12.9 mi / 20.7 km)
  • Glenora Wine Cellars (12.9 mi / 20.8 km)
  • Ravines Wine Cellars on Seneca Lake (13 mi / 20.8 km)
  • Hazlitt 1852 Vineyards (13.8 mi / 22.2 km)

Exploring the natural features in Penn Yan

Whether you're an active traveller or just want to take in the scenery, Penn Yan is a great place to spend some time outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Keuka Lake Outlet Trail (2.6 mi / 4.2 km)
  • Keuka Lake State Park (6.8 mi / 10.9 km)
  • Seneca Lake (7.6 mi / 12.3 km)
  • Sampson State Park (9.1 mi / 14.7 km)
  • Keuka Lake (12.5 mi / 20 km)
  • Canandaigua Lake (15.2 mi / 24.4 km)

Transport to and around Penn Yan

The nearest airport is in Ithaca, NY (ITH-Tompkins Regional), located 32.7 mi (52.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Elmira, NY (ELM-Elmira - Corning Regional), which is 35.3 mi (56.9 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Penn Yan?
Houses are the most popular type of holiday rental in Penn Yan, according to our data. Even if you have something else in mind, Vrbo has holiday homes in loads of sizes and shapes. Compare our options to find your perfect fit.
How much does it cost to rent a holiday rental in Penn Yan?
The average price for a holiday home in Penn Yan can vary based on factors like length of stay, property type and season. Whether you're looking for a sprawling house with room for friends and family or a cosy cottage just enough for two, just enter your travel dates to see stays with exceptional value.
How much does it cost to rent a beach house in Penn Yan?
The average price for a holiday rental close to the beach in Penn Yan will depend on when you're going and the size and style of property you want. Find prices easily on Vrbo by entering your dates of travel. Then use the handy filters to select the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday rentals in Penn Yan?
Yes, there are. You can pick from 14 holiday rentals that cater to pets in Penn Yan. Plenty of our pet-friendly holiday rentals come with a garden for your furry pal to play around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Vrbo.
What are popular rental amenities in Penn Yan?
Some of the most popular rental amenities people look for in Penn Yan are nearby museums, a garden and a water view. Whether you're holidaying with pals, family or even pets, Vrbo holiday properties have the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday rentals in Penn Yan?
Penn Yan has four holiday homes that can host 10 or more guests. These stays come with the space and privacy you need to enjoy good times with friends and family.
Are there holiday rentals in Penn Yan that welcome kids?
Gather your whole crew for the adventure of a lifetime in Penn Yan at one of our 14 family-friendly holiday properties. A lot of these stays feature amenities that are perfect for trips with the kids, such as laundries, extra bedrooms and entertainment areas. Just check the "Properties good for families" filter and decide on your favourite.
What are the top attractions for families in Penn Yan?
Keep the kids busy at these leading family-friendly attractions in Penn Yan:
  • Keuka Lake State Park
  • Keuka Lake Outlet Trail
  • Arts Centre of Yates County
Are there one-bedroom holiday rentals in Penn Yan?
Yes, you can pick from three one-bedroom rentals in Penn Yan. Whether you're on the lookout for a cosy chalet or a condo, our one-bedroom properties are great if you don't require a lot of space. One of the best things about having your own pad? You'll never need to share your trip with strangers.
Can I find two-bedroom holiday rentals in Penn Yan?
Gather your besties and enjoy a relaxing escape in one of the four two-bedroom holiday homes Penn Yan has to offer.
How can I find holiday rentals with air conditioning in Penn Yan?
Penn Yan has 13 holiday rentals where you'll be able to chill out in air-conditioned comfort. To find a property on Vrbo that has this perk, enter your preferred travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Penn Yan?
You'll need to check with the Penn Yan holiday property you're looking at on Vrbo as the minimum age varies. However, it's typically 16, 18 or 21.
How long can I rent a holiday rental in Penn Yan for?
The amount of time you can stay in a Penn Yan holiday rental for depends on each property. Just put in your dates of travel to view available options offering longer term stays. They include all the things you need to make your extended trip more convenient and comfortable, such as kitchens and yards. Some Vrbo holiday rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

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