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:25 Dec - 1 Jan

Interior
Interior
Dining
Exterior
Exceptional
(10 reviews)

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

Pulteney

8% off
AU$10,049
for 7 nights, 1 cabin
AU$1,436 per night
includes taxes & fees
Finger Lakes Lodge overlooking Keuka Lake with 1st floor master bed & bath!
Kitchen w/ view of back patio w/ firepit and grill
Beach front
A guest's watercolor of the Lake House
walk way to the front porch
Exceptional
(117 reviews)

Idyllic Lakeside Victorian Farmhouse

Rock Stream

8% off
AU$8,418
for 7 nights, 1 home
AU$1,203 per night
includes taxes & fees
Idyllic Lakeside Victorian Farmhouse
Living area
Outdoor dining
Property grounds
Exterior
Exceptional
(15 reviews)

Beautiful Seneca Lake Chalet with stunning lake and Pond views

Penn Yan

7% off
AU$2,425
for 7 nights, 1 chalet
AU$346 per night
includes taxes & fees
Beautiful Seneca Lake Chalet with stunning lake and Pond views
Grill on back deck for outdoor cooking.
Interior
Fully stocked kitchen
Vinyl waterproof flooring in the kitchen.
Exceptional
(151 reviews)

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

Branchport

8% off
AU$1,059
for 7 nights, 1 cabin
AU$151 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
AU$18,603
for 7 nights, 1 cottage
AU$2,658 per night
includes taxes & fees
Cozy Cottage with 45' Lake Frontage and Kayaks
Living area
Exterior
Property grounds
Living area
Exceptional
(14 reviews)

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

Penn Yan

6% off
AU$10,704
for 7 nights, 1 cottage
AU$1,529 per night
includes taxes & fees
Private, Rustic, Quiet, Quirky! Welcome to O'Cottage! 150 feet of lake frontage
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
AU$2,050
for 7 nights, 1 cottage
AU$293 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
AU$2,467
for 7 nights, 1 cabin
AU$352 per night
includes taxes & fees
Bluebird Cabin - Brand New Cozy Log Cabin on 5-Wooded Acres / Pet-Friendly!
den area
Southside porch
bedroom down east facing
1.9 acres with dock, house view to cottage
Exceptional
(5 reviews)

Charming 4-bedroom house with WiFi and AC in Branchport

Branchport

8% off
AU$9,699
for 7 nights, 1 home
AU$1,386 per night
includes taxes & fees
Charming 4-bedroom house with WiFi and AC in Branchport
Private kitchen
Property grounds
Exterior
Outdoor dining
Wonderful
(113 reviews)

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

Dundee

20% off
AU$9,648
for 7 nights, 1 home
AU$1,378 per night
includes taxes & fees
Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch
New Kitchen Island
Sunset photo using iPhone on portrait mode.
Outdoor spa tub
Open from Memorial Day through Labor Day
Exceptional
(189 reviews)

VRFLX Seneca Lake Access | Walk to Beach

Hector

12% off
AU$7,768
for 7 nights, 1 home
AU$1,110 per night
includes taxes & fees
VRFLX Seneca Lake Access | Walk to Beach
2nd floor: Master bedroom, walk-out balcony, master beds, chair, TV, fireplace
Newly remodeled kitchen 2022 with beautiful solid surface countertops
View of the house from the driveway
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
AU$14,070
for 7 nights, 1 home
AU$2,010 per night
includes taxes & fees
Dreaming a View - Tranquil Retreat on Seneca Lake - Sleeps 12
3 seasons sun room
View from the living room
Exterior
Overhead view of the living room
Exceptional
(167 reviews)

Chalet overlooking Keuka Lake in the heart of Wine Country

Penn Yan

15% off
AU$1,352
for 7 nights, 1 chalet
AU$193 per night
includes taxes & fees
Chalet overlooking Keuka Lake in the heart of Wine Country
Campfires by sunset are an enjoyable family experience!
Private pool area behind the house
Chef's kitchen with sliding doors to patio and window overlooking the playground
Interior
Exceptional
(95 reviews)

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

Ovid

8% off
AU$5,869
for 7 nights, 1 home
AU$838 per night
includes taxes & fees
Lake House Open Year-Round! Summer Pool Fun & Fireplace Cozy Winter Retreat.
Private kitchen
Property grounds
Living area
Beautiful sight at sunset!
Exceptional
(49 reviews)

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

Penn Yan

8% off
AU$4,782
for 7 nights, 1 home
AU$683 per night
includes taxes & fees
Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23
Enjoy the campfire
Spacious living room
coat hooks in garage entry
View of kitchen from living room
Exceptional
(200 reviews)

Friends And Family Farmhouse

Penn Yan

8% off
AU$5,771
for 7 nights, 1 home
AU$824 per night
includes taxes & fees
Friends And Family Farmhouse
Interior
Private kitchen
Living area
Property grounds
Exceptional
(24 reviews)

The Ideal Vacation Location in the Heart of Wine Country

Penn Yan

8% off
AU$2,649
for 7 nights, 1 home
AU$378 per night
includes taxes & fees
The Ideal Vacation Location in the Heart of Wine Country
Living area
Outdoor dining
Private kitchen
Exterior
Exceptional
(193 reviews)

Serenity Zen House on Seneca Lake - Pet Friendly

Penn Yan

8% off
AU$5,199
for 7 nights, 1 home
AU$743 per night
includes taxes & fees
Serenity Zen House on Seneca Lake - Pet Friendly
New couch and love seat
Living area
Dining
Beautifully manicured grounds
Exceptional
(127 reviews)

Immaculate Summer Home on Seneca Lake

Romulus

8% off
AU$4,071
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Immaculate Summer Home on Seneca Lake
Private kitchen
Outdoor dining
Interior
Room
Exceptional
(14 reviews)

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

Hector

8% off
AU$7,259
for 7 nights, 1 home
AU$1,037 per night
includes taxes & fees
Modern A-Frame near many wineries and activities: fire pit, King beds, & more!
Property grounds
Exterior
Private kitchen
Room
Exceptional
(19 reviews)

Cozy Cabin get away to Finger Lakes Wine Country

Geneva

8% off
AU$1,677
for 7 nights, 1 cabin
AU$240 per night
includes taxes & fees
Cozy Cabin get away to Finger Lakes Wine Country
Interior
Living area
Living area
Living area
Exceptional
(18 reviews)

Meticulously designed waterfront, 4 level home, on sought after Keuka Lake!

Hammondsport

16% off
AU$8,292
for 7 nights, 1 home
AU$1,185 per night
includes taxes & fees
Meticulously designed waterfront, 4 level home, on sought after Keuka Lake!
Deck, pool and rear yard view. Privacy and fun combined.
A charming rental home located in the heart of the Finger Lakes region.
Multi-acre property with extra amenities just minutes from Keuka Lake.
Perfect setting to enjoy evening sunsets over Keuka area hills.
Exceptional
(35 reviews)

Finger Lakes House has private Pool, Fire Pit & Extra Amenities in Hammondsport

Hammondsport

7% off
AU$3,387
for 7 nights, 1 home
AU$484 per night
includes taxes & fees
Finger Lakes House has private Pool, Fire Pit & Extra Amenities in Hammondsport
Dining
Serenity Aloft
Exterior
Kitchen
Exceptional
(118 reviews)

Serenity on Seneca House - A Slice of Paradise

Penn Yan

8% off
AU$5,974
for 7 nights, 1 home
AU$853 per night
includes taxes & fees
Serenity on Seneca House - A Slice of Paradise

  • 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 best area to stay in Penn Yan when booking a holiday rental?
When considering the best area to stay in Penn Yan for a holiday rental, the downtown area emerges as a fantastic option. This vibrant neighbourhood offers a charming blend of local shops, cafes, and restaurants, creating a lively option that is superb for visitors. With a variety of properties available, from cosy cottages to more spacious homes, there's something to suit every taste and budget.One of the highlights of staying in downtown Penn Yan is the proximity to Keuka Lake, which is renowned for its stunning views and recreational opportunities. Visitors can enjoy activities such as boating, fishing, and swimming, making it an ideal spot for outdoor enthusiasts. Additionally, the nearby Keuka Lake Vineyards provide a wonderful opportunity for wine lovers to sample some excellent local wines while taking in the picturesque scenery.Another appealing aspect of this area is its rich history, which can be explored through attractions like the Penn Yan Museum. This small but informative museum offers insights into the local heritage and is a delightful stop for those eager to learn more about the region.
Where are the best areas for renting a beach house in Penn Yan?
For renting a beach house in Penn Yan, the area along the northern shore of Keuka Lake is particularly appealing. This charming region features a variety of holiday rentals with direct access to the lake, offering stunning views and opportunities for water activities. Many properties here come equipped with essential amenities such as private docks, outdoor seating areas, and fully equipped kitchens, making them suitable for families and groups looking to enjoy a lakeside retreat.The Penn Yan area is also home to several local wineries and vineyards, which are well worth exploring. Rentals in this vicinity often provide easy access to wine trails, and some properties include outdoor spaces for wine tasting or barbecuing after a day of exploration. Additionally, the nearby Keuka Lake State Park offers hiking trails and picnic areas, enhancing the outdoor experience.In the town of Penn Yan itself, visitors can find charming cottages and homes that reflect the local architecture, often featuring amenities like air conditioning, Wi-Fi, and landscaped gardens. These accommodations provide a comfortable base for enjoying the nearby beaches and local attractions, including shops and restaurants that showcase the region's unique culture.
What is the most popular type of holiday rental accomodation in Penn Yan?
In Penn Yan, holiday houses are the most popular type of holiday rental, with around 540 available in the area. These properties are typically spacious and well-equipped, featuring multiple bedrooms, full kitchens, and often outdoor spaces such as decks or patios, superb for enjoying the scenic views of Keuka Lake. Additionally, there are about 200 cottages that offer a charming, rustic experience, often situated near the water, providing a cosy retreat for couples or small families. For those seeking a more secluded experience, around 52 cabins are available, which usually include amenities like fireplaces and access to hiking trails. There are also approximately 48 apartments, offering more urban living options close to local shops and restaurants.
Are there any family house rentals in Penn Yan?
In Penn Yan, New York, there are numerous family-friendly house rentals available, with around 164 properties to choose from. This charming town is situated by the beautiful Keuka Lake, offering a tranquil setting for families. Many of these homes come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces great for children to play. Visitors can expect amenities such as Wi-Fi and air conditioning for added comfort during their stay.The surrounding area boasts various attractions, including wineries and scenic walking trails, allowing families to explore the natural beauty of the Finger Lakes region. Additionally, nearby parks provide opportunities for outdoor activities such as hiking, fishing, and picnicking.
Can I rent a holiday home with a pool or hot tub in Penn Yan?
In Penn Yan, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for travellers seeking relaxation and recreation. This charming town, located on the shores of Keuka Lake in the Finger Lakes region, offers a range of accommodations, from lakeside cottages to spacious family homes.Many of these properties come equipped with private pools or hot tubs, superb for unwinding after a day of exploring the area's natural beauty and wineries. Expect amenities such as fully equipped kitchens, outdoor patios, and scenic views of the lake, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Penn Yan?
In Penn Yan, there are numerous pet-friendly house rentals available, with around 79 options for travellers seeking accommodations that welcome their furry companions. Many of these rentals offer home-like amenities, such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.The area is particularly appealing for pet owners due to its proximity to stunning natural landscapes and recreational opportunities. Seneca Lake, just a short distance away, features parks and walking trails that are superb for leisurely strolls with pets, while the nearby Keuka Lake State Park offers beautiful hiking paths and scenic views. Additionally, the charming village atmosphere provides pet-friendly cafes and shops, enhancing the overall experience for those travelling with dogs or other pets.
Are there any remote work holiday rentals in Penn Yan?
In Penn Yan, New York, there are numerous options for remote work holiday rentals, with around 776 properties available to choose from. This charming town, located on the shores of Keuka Lake, offers a peaceful environment ideal for those looking to balance work and leisure. Many of these rentals come equipped with reliable Wi-Fi, allowing for productive work sessions, and some even feature dedicated workspaces to enhance your remote working experience.The area is dotted with lovely lakeside homes, cottages, and townhouses that provide comfortable amenities such as fully equipped kitchens, spacious living areas, and outdoor decks to enjoy the stunning lake views. Additionally, the proximity to local attractions, including vineyards and beautiful hiking trails in the Finger Lakes region, adds to the appeal of working remotely here. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Penn Yan?
In Penn Yan, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and outdoor spaces such as decks or patios for relaxation and enjoying the scenic surroundings. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, many rentals feature coffee and tea makers, ensuring that guests can enjoy a warm beverage at their leisure.
When is the best time to visit Penn Yan for a holiday rental?
The best time to visit Penn Yan for a holiday rental is during the peak season from June to August. This vibrant period attracts many travellers eager to experience the beautiful Finger Lakes region, with July being particularly popular. Visitors can revel in pleasant summer temperatures, typically ranging from 15 to 30 degrees Celsius, making it ideal for outdoor activities such as boating, hiking, and wine tasting.During these months, the area's stunning natural scenery comes alive, and you'll find a lively option with numerous festivals and events, including local farmers' markets and art shows. The charm of Penn Yan, combined with its beautiful lakeside views, makes it a fantastic spot for those seeking both adventure and relaxation.For those looking for a more budget-friendly option, consider visiting in December. Although this month is part of the low season, it offers a great experience with fewer crowds and a peaceful winter landscape. It's a great time to enjoy the local holiday festivities and the serene beauty of the Finger Lakes.Ultimately, choosing between the energetic summer months or the tranquil winter season will depend on your travel preferences.
What are the top attractions in Penn Yan?
In Penn Yan, visitors can enjoy a range of attractions that highlight the area's natural beauty and local culture. The picturesque Keuka Lake is a major draw, offering opportunities for boating, fishing, and relaxing by the water. The lake's scenic views can be appreciated from various parks, such as Keuka Lake State Park, which features hiking trails and picnic areas.The Finger Lakes region is renowned for its wineries, and many visitors take advantage of the nearby wine trails, with several vineyards offering tastings and tours. The quaint downtown area of Penn Yan is also worth exploring, boasting charming shops, restaurants, and local art galleries that reflect the town's heritage.For those interested in history, the Penn Yan Museum provides insights into the local history and culture, while the nearby village of Dresden features historic sites associated with the region's early settlers.
Are all fees included in the Penn Yan holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Penn Yan holiday homes with parking?
Stayz offers a wide selection of holiday homes in Penn Yan with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Penn Yan holiday homes?
You can find great discounts on holiday homes in Penn Yan on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Penn Yan holiday home booking on Stayz?
To find Penn Yan holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Penn Yan?
A long-stay holiday home in Penn Yan is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Penn Yan holiday home?
Book your Penn Yan holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Penn Yan?
Prices for holiday homes in Penn Yan vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Penn Yan to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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