Vacation Home Rentals By Owner In Penn Yan, NY

$1318.34

Seneca Lakefront | Hot Tub, Sauna & Epic Game Room / Bar

Penn Yan, New York, United States

This lakefront retreat on Seneca Lake is designed for groups who want space, views, and built-in entertainment—not just a place to sleep. The property includes a two-story main house and a detached garage with additional sleeping and recreation space.brbrThe main house features three bedrooms and two full bathrooms, including a main floor bedroom with a queen bed, an upstairs king bedroom, and an upstairs queen bedroom. There is a fully stocked kitchen, a spacious living room with panoramic lake views, and a cozy library room in the main house for relaxing indoors, which also includes a sleeper sofa for additional shared sleeping.brbrThe detached garage adds flexible sleeping and a large entertainment area. Upstairs, there is a king bed in an open layout without a door, along with a twin bed in a shared common space and a sleeper sofa in the loft area. There is also a full bathroom and an expansive game room with a pool table, ping pong, shuffleboard, foosball, air hockey, a poker table, and a bar. Washer and dryer access is located in the garage.brbrOutside, the property offers direct lakefront access along with multiple spaces to unwind. Guests can enjoy the hot tub overlooking the water, relax in the barrel sauna, or take in the views from the deck. The setting is quiet and scenic, making it easy to spend most of your time right on the property.brbrThe home is a short drive to wineries, breweries, and downtown Penn Yan, but it’s especially well suited for guests who plan to enjoy the lake, amenities, and time together on-site. It works best for families, multiple couples, or groups who are comfortable with a mix of private and semi-private sleeping arrangements.

Bed

Bath

Sleeps

$381.66

/ Nightly

Private Vacation Home

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

Penn Yan, New York, United States

Step back in time at this beautifully restored Victorian home in the heart of Finger Lakes wine country, where classic charm meets modern comfort — and where staying feels a bit like stepping onto the set of the movie It’s a Wonderful Life. Located just minutes from the Seneca and Keuka Lake wine and beer trails, and within walking distance to shops, dining, and nightlife in downtown Penn Yan, this home offers the rare combination of history, space, and unbeatable walkability.brbrComfortably sleeping a larger group, the home is especially well suited for girls’ weekends, family gatherings, and relaxed group getaways, with plenty of room to gather and unwind.brbr Why Guests Love this Victorian Home:brbr- Walk to Penn Yan shops, restaurants, wine bars, and nightlifebrbr- Private hot tub for relaxing eveningsbrbr- Fire pit, grill, rear patio, and front porch for outdoor livingbrbr- Large private yardbrbr- Minutes to Seneca & Keuka Lake wine and beer trailsbrbr- Two parlors ideal for group conversationsbrbr- Large eat-in kitchen perfect for shared mealsbrbr- Fireplace and beautifully refinished original hardwood floorsbrbr- Two stairways that add to the home’s historic characterbrbrOther things to note:brbrInterested in enhancing your stay We can provide recommendations for local services to make your trip even more special. Please note that these services are arranged directly with local providers and have additional costs:brbr- In-cottage massagesbrbr- Private wine toursbrbr- Kayak and canoe rentalsbrbr- Boat rentalsbrbr- Bike rentalsbrbr- Horseback ridingbrbrThis cottage is part of the Savannah House Wine Country Inn and Cottages, so you'll enjoy the same level of hospitality and service that we've extended to all of our guests for almost 20 years!brbr*Pets are not allowed at this property. No exceptions.

Bed

Bath

Sleeps

$281.7

/ Nightly

Private Vacation Home

Pet-Friendly Penn Yan Home: Wineries, Parks, Lakes

Penn Yan, New York, United States

Escape to the heart of New York’s wine country with a stay at this vacation rental in Penn Yan! With a 2,493-square-foot interior boasting 3 bedrooms, 2 bathrooms, and a loft, this charming home has room for everyone in your crew. Spend your days exploring the acclaimed Finger Lakes wineries, or embark on a scenic hike on the Keuka Outlet Trail. Each evening, return home to stargaze in the private backyard before curling up with a book in the living room as you await your next adventure.brbr-- THE PROPERTY --brbrDeck | Free WiFi | Keyless EntrybrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Loft: 2 Twin BedsbrbrMAIN FEATURES: Cable TV, fenced backyard, booksbrKITCHEN: Stove/oven, microwave, refrigerator, coffee maker, dishwasher, toaster, dishware/flatware, trash bags/paper towelsbrGENERAL: Central A/C, washer/dryer, linens/towels, hair dryerbrFAQ: Pet fee (paid pre-trip)brSUITABILITY: Stairs required for access, bedrooms on 2nd floorbrPARKING: Driveway (3 vehicles)brADDT’L ACCOMMODATIONS: An additional property is available on the same block with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrTHINGS TO DO: Keuka Arts Festival (0.4 miles), Seneca Mill & Falls (3 miles), Saunders Finger Lakes Museum (8 miles), Glenn H Curtiss Museum (22 miles), National Women's Hall of Fame (27 miles)brVINO: Keuka Lake Wine Trail (1 mile), Anthony Road Wine Company (6 miles), Point of the Bluff Vineyards (16 miles), Heron Hill Winery (20 miles), Cayuga Lake Wine Trail (29 miles) brON THE WATER: Morgan Marine (1 mile), East Bluff Harbor (7 miles), Basin Park Marina (8 miles), Keuka Lake (14 miles), Roy's Marina (14 miles) brOUTDOOR REC: Parking for Seneca Mills Falls (0.9 miles), Indian Pines Park (2 miles), Keuka Lake State Park (8 miles), Scenic Overlook (10 miles), Seneca Lake State Park (16 miles) brAIRPORTS: Elmira Regional Airport (44 miles), Frederick Douglass Greater Rochester International Airport (60 miles), Syracuse Hancock International Airport (71 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Stairs are required to enter and access all bedrooms

Bed

Bath

Sleeps

$324.67

/ Nightly

Private Vacation Home

Pet Friendly Keuka Yurt

Penn Yan, New York, United States

Nestled on 6 acres near Keuka Lake, this all-season Yurt offers the perfect blend of relaxation and adventure. Enjoy a complimentary cup of coffee, stargaze under the dome, and explore nearby wineries and Watkins Glen. Amenities include: cozy queen bed, full kitchen, heat & A/C, fast Wi-Fi, and outdoor fire pit. Plus, we don’t charge a pet fee—bring your furry friends!brbrHave questions Message us anytime—we’re happy to help!brbrLOCATION brLocated approximately 7 miles South of the Village of Penn Yan, the Yurt sits just off the main route on a wooded 6-Acre parcel of land on the East side of Keuka Lake. This lot is located on the side of a hill and approximately 1/4 mile from the lake. This property does not have access to the lake. The lake can be seen from the end of the driveway. We fall in the middle of the Wine Trail between Rooster Hill Vineyard & Weis. We are approximately 17 Miles from Watkins Glenn State Park, 7 Miles from the Keuka Lake Outlet Trail & 14 Miles from the Keuka Lake State Park. brbrAMENITIES / DISCLOSURESbrThe Yurt offers all the same comforts of a hotel room & more. The Yurt is a canvas tent built with the snow package for the interior installation, keeping the Yurt warm in the winter & cool during the summer. It is heated with a Mini Split (forced air heat/AC) that is temperature controlled with a remote control. Temperature is always set to 70 degrees before your arrival and you can adjust it as you need during your stay. brbrThe Yurt is plumbed for the kitchen & bathroom. The water source is from a Well that contains sulfur only noticeable when hot water is running. We supply basic cooking materials such as pots, pans, cups, plates, silverware. The kitchen has a sink, cupboards, a mini refrigerator, oven & stove top. brbrGuests will have access to WiFi during their stay. The Smart TV will already have Netflix logged in for you. brbrThe couch is a small futon. The second queen bed is not a physical bed and is described just as it's showing in the pictures as an adult-size bean bag chair that will fold out into a queen size mattress. brbrCoffee is provided for you. The Keuirg will have the coffee pods, sugars & creamer all located in the drawers beneath. brbrFull bathroom with a shower, sink & toilet. We provide shampoo, body wash and towels. If you require special soaps please bring your own. brbrWe are pet friendly, which means that other guests who have stayed have brought their pets here. We don't charge additional pet fees. We have an excellent cleaning crew but if you are sensitive and have pet allergies, this rental may not be for you. brbrWe have the Yurt professionally treated by a local pest control company two times a year. Once in the spring & once in the fall. Although we are proactive in treating the Yurt there is no perfect solution for a Yurt in the woods. If you can't handle the site of insects this rental may not be for you. Guest who stay during the winter, when it gets cold out the mice will try to get in. We do place traps out and remove anything we catch. Occasionally, that process happens while a guest is staying. If mice frighten you, this rental may not be for you. brbrWood is not provided for the fire pit. There are several of near by stands you will pass on your way to the property. Buying wood from our neighbors helps keep them happy!

Bed

Bath

Sleeps

$210.72

/ Nightly

Private Vacation Home

Hollow Hills Tiny Home

Penn Yan, New York, United States

Brand new double lofted Tiny Home on wheels located upon a private country hillside. Overlooking the hills of Keuka Lake, guests can enjoy radiant sunrises, knowing they are just minutes from the local wine trail/ breweries, Crispin Hill Wedding Venue, Apple/ Grape picking, the list goes on! While enjoying a cup of coffee, guests can take in a quiet and tranquil morning, all while being just a half mile from the Village of Penn Yan. Stay connected with our wifi, or just relax by the fire! Hillside rural farm country in the heart of the Finger Lakes less than a half mile from the Village of Penn Yan. Long Private driveway

Bed

Bath

Sleeps

$459.2

/ Nightly

Private Vacation Home

Beautiful 3 bedroom chalet near Keuka Lake

Penn Yan, New York, United States

Get ready to relax in this 3-bedroom house in Penn Yan. Our Chalet is a newly remodeled house on the edge of Penn Yan within sight of Keuka Lake. Seasonal lake views and beautiful sunset skies. A stones throw from Morgan Marine and Red Jacket park. Walking distance from restaurants and a public beach.br Master bedroom on main floor with queen bed and access to bathroom. Two bedrooms upstairs and large bathroom. Comfortably sleeps 6-8 people. Large eat in kitchen fully stocked for cooking at home.

Bed

Bath

Sleeps

$265.65

/ Nightly

Private Vacation Home

Keuka Village House, Penn Yan

Penn Yan, New York, United States

Looking for a whole house to stay in the Finger Lakes This is your next vacation rental in Penn Yan, NY! With 3 bedrooms and 1.5 baths, this village home is the perfect setting for a relaxing getaway. You will be close to Keuka Lake’s 32 wineries, 10 breweries, 3 distilleries, and endless opportunities for outdoor fun at your fingertips. Trek the 7-mile Keuka Lake Outlet Trail, make a splash in the lake at Indian Pines Park, or walk to downtown Penn Yan for shopping, dining, and nightlife.br

Bed

Bath

Sleeps

$346.04

/ Nightly

Private Vacation Home

Relaxing two-story home with a deck, firepit, game room, & washer/dryer

Penn Yan, New York, United States

Wine Trail Basecamp: 3BR Home near Keuka Lake & Windmill MarketbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to Cozy Family Home, managed by Vacasa. This house is located in Penn Yan but your 24/7 support is always nearby.brbrThis house features three bedrooms and two bathrooms with space enough for six.brbrPlease review our property photos and our available amenities to make sure this rental is a perfect fit for your needs. We strive to keep this information as up-to-date as possible so you can feel confident in knowing what you are renting.brbrWe will send you all necessary pre-arrival and check-in information after booking. This can include guest instructions, notices, and other helpful information.brbrWhat We LovebrRelax & Recharge in the Heart of the Finger Lakes!brEscape to this charming two-story retreat—perfect for a family vacation or a getaway with friends! Whether you're seeking relaxation or adventure, this home offers the best of both worlds.brUnwind in comfort or head out and explore the area! You'll be just minutes from downtown Penn Yan, where local shops and restaurants await. Take a dip in Keuka Lake, cast a line for some phenomenal fishing, or sip your way through nearby wineries and breweries. For outdoor enthusiasts, state parks and the scenic Majestic Hills Golf Course are just a short drive away.brbrThe well-equipped, galley-style kitchen makes it easy to start your day with a fresh cup of coffee, pack snacks for lake adventures, or prepare a full meal to enjoy at the dining table or out on the covered, furnished deck.brAfter mealtime, enjoy some friendly competition with yard games in the spacious backyard, or settle into the cozy main living area to stream your favorite shows. Feeling playful Head downstairs to the finished basement—complete with a Ping-Pong table, dartboard, second TV, and a comfy seating area. There’s even a quiet nook with dual desks, perfect for remote work or school.brbrWhen the day winds down, gather around the backyard firepit to roast s’mores, share stories, or simply relax under the stars. Additional amenities include air-conditioning, a gas fireplace in the main living room, a washer/dryer, and a grill for sunny-day cookouts.brbrHouse RulesbrCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll guests shall abide by Vacasa's good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.brVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrParking notes: There is free parking available for 5 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Bed

Bath

Sleeps

$310.2

/ Nightly

Private Vacation Home

“QKA Retreat” on Keuka Lake

Penn Yan, New York, United States

**There is no availability for summer 2026** A renters dream! Located close to the Village of Penn Yan and right in the heart of Finger Lakes wine country, this 4 bedroom, 2 bath lake house makes for the perfect getaway from the hustle and bustle of everyday life.brbrGreat for families to rent with plenty of relaxing activities close by. Located on the east lake side, you’re within walking distance to a local park, close proximity to the movie theater and bowling alley just in case a rainy day keeps you from the lake, or stay inside and enjoy the family board games. A large deck for dinners and entertaining includes two electric retractable awnings making it the perfect spot to watch the beautiful Keuka sunsets. Your own private dock to go fishing, two kayaks provided for exploring the lake and a fire pit for smores filled evenings.brbrLooking to get out for a bit The Keuka Wine Trail is a must and Seneca Lake is just quick drive from the house. The Village of Penn Yan offers coffee shops, local shops, bistros, bars and breweries, etc. Lakeside Country Club is right nearby as well.brbrOn site laundry is provided, plenty of closet space in the house along with ample parking (which is hard to come by on the lake!). Note, two full baths, one with a shower and a tub in another. The house is “all-seasons”, connected to city water with forced air heating and air conditioning.brbrOn a personal note, this isn't our fulltime job. We are 2 working parents to 2 young kids with the hope when we retire we can be at the lake more permanently. We do utilize the house for personal use throughout the year. We attempt each year to make updates to the house to allow for a positive renter's experience. Some highlights for 2023 and 2024 include the following: extended the dock which includes an end patio, replaced large outdoor dining table which increased capacity from 6 to 8 people, updated grill, purchase new bedding and towels, replaced indoor rug, replaced kitchen items and purchased new AC units for 2 bedrooms.brbrSorry, no pets! No smoking in the house! Minimum age to rent: 30 years old. Dock and AC in all rooms is guaranteed to be in Memorial Day - Labor Day. brbrPlease feel free to ask any questions!

Bed

Bath

Sleeps

$1053.22

/ Nightly

Private Vacation Home

Steinhus: Stunning Stone Estate with 200' Private Keuka Lakefront!

Penn Yan, New York, United States

Welcome to Steinnhus, a beautiful stone Finger Lakes vacation rental on the East Bluff of Keuka Lake. This unique vacation home includes three stone buildings nestled in a serene clearing, offering 200 feet of lake frontage and stunning views.brbrThe main house features a “Cook's Kitchen” filled with cooking essentials, a spacious great room with a decorative stone fireplace, and floor-to-ceiling windows showcasing the lake. There are two bedrooms — one king with lake views, and one queen with garden views — plus a bathroom with a walk-in stone shower.brbrSteps away, the guest house studio offers a queen bed and a private pergola, perfect for a quiet afternoon. The ensuite guest house features a king bed, living area, custom bar, and a bathroom with a walk-in stone shower.brbrOutside, enjoy the balcony, pergola, and large dock for fishing, sunbathing, and relaxing by the water.brbrLocated just minutes from Penn Yan and nearby wineries, Steinnhus is the ideal Finger Lakes vacation home for families or couples. Book your stay now!brbrYour safety matters to us! Steinnhus has two exterior security cameras. The cameras do not look into any interior living areas.brbrNote: br1. Smoking is not allowed in any rental property. This includes vaping and e-cigarettes. br2. Homes are not handicap accessible, unless stated in the description.br3. Air conditioning is not available unless listed as an amenity. If available, air conditioning is considered a seasonal amenity and is only available May 15 - October 15.br4. Where pets are allowed it is indicated. Otherwise, pets are not allowed. Homes are not guaranteed allergen-free, even those that do not allow pets.br5. Docking capabilities may vary based on current water levels. Docking is not guaranteed if water levels are low and/or high due to seasonal weather and climate changes.br6. Outdoor amenities, including furniture, watercraft and firepit are not available between October 15 - May 15.

Bed

Bath

Sleeps

$1480.21

/ Nightly

Private Vacation Home

Lakefront Home with Spectacular Views, Sleeps 18!

Penn Yan, New York, United States

If you are looking for a home away from home, FineView Cottage is it! Our 4200 sq. ft. home is fully furnished and made for your relaxation featuring 6 bedrooms (5 queen beds and 9 twin beds), 3 full and 3 half bathrooms, living room (with a queen pull out sofa bed), family room with a stone gas fireplace, dining room and a kitchen with many of the amenities you are accustomed to. Wake up to beautiful sunrises and enjoy 175 feet of level, walk-in lake frontage. There is plenty of room for family and friends to enjoy the outside on the large lawn, beach, and patio areas. Our two docks offer a place to park your boat, with plenty of room to still enjoy swimming and floating. The public boat launch in Penn Yan is only a few short miles away. If you want to relax at the house and still enjoy the lake, take a seat on one of the rocking chairs and enjoy the view from our spacious porch. Finish off your day with a camp fire and fall asleep in one of the large bedrooms to the gentle breaking of wave’s right outside of your window. brbrFineView is nestled in the Keuka Lake Wine Country and is close to wonderful shops, wineries, museums, and restaurants. The charming Windmill market, originally an Amish trading center, operates every Saturday morning in the summer months where you will find the freshest produce, cultivated and wild flowers, handmade furniture, delicious homemade pies and other delicacies.brbrKeuka Lake (known as the'Y' lake) is the cleanest Finger Lake... great for fishing, swimming, canoeing, kayaking, sailing, and water skiing. There are several marinas around the lake and motor boats may be rented by the day or week and tied up to the dock. brbrWe hope you enjoy this special spot as much as our family does and return year after year.brbrBest,brThe Dix Family

6

Bed

4

Bath

16

Sleeps

$1168.4

/ Nightly

Private Vacation Home

Bolton Landing on the Bluff: Breathtaking Keuka Lake Views!

Penn Yan, New York, United States

What's the best part of renting a classic lake home The view—and at Bolton Landing on the Bluff, you'll enjoy some of the most breathtaking scenery on Keuka Lake, from sunrise to sunset. Nestled along East Bluff, this spacious getaway is just minutes from award-winning wineries and the charming town of Penn Yan, giving you endless ways to explore the Finger Lakes.brbrInside, knotty pine accents create a warm, rustic atmosphere throughout. A galley kitchen welcomes you and sets the stage for memorable family meals—made even better with fresh, local finds from the Windmill Farm Market. In the great room, wall-to-wall windows frame a sweeping panoramic view of the lake, so you can enjoy the scenery rain or shine. The main level also features two private bedrooms, each with a queen bed.brbrUpstairs, a semi-private loft offers a twin trundle that converts into a king, plus a private en suite bath. The lower level completes the home with four additional bedrooms, making room for the whole family. Two primary bedrooms with king beds and lake views are most near the lower level patio door. No matter where you sleep, each bedroom provides a cozy retreat after a day of lake adventures.brbrStep outside and take your pick between a sunny balcony or a shaded patio for lakeside lounging. A spacious lawn leads to 226 feet of gradual lakefront—perfect for swimming, fishing, sunbathing, or simply soaking in the view. A hot tub on the north side of the house allows you to relax in the bubbly waters all year round!brbrConveniently located just south of Penn Yan, you'll be close to local favorites like Seneca Farms Ice Cream, The Keuka Restaurant and Amity Coffee House. And of course, no Finger Lakes vacation is complete without a stop at a winery or brewery—Heron Hill Vineyards, Keuka Spring Winery, and Abandon Brewing are just minutes away.brbrMake your reservation today and discover why a Keuka Lake getaway at Bolton Landing on the Bluff will have you coming back year after year.brbrOccupancy: This property is closely monitored for responsible renting. The maximum occupancy of each home is the number of guests allowed on the premises at any given time. This includes both day and overnight guests. brbrNote: br1. Smoking is not allowed in any rental property. This includes vaping and e-cigarettes. br2. Homes are not handicap accessible, unless stated in the description.br3. Air conditioning is not available unless listed as an amenity. If available, air conditioning is considered a seasonal amenity and is only available May 15 - October 15.br4. Where pets are allowed it is indicated. Otherwise, pets are not allowed. Homes are not guaranteed allergen-free, even those that do not allow pets.br5. Docking capabilities may vary based on current water levels. Docking is not guaranteed if water levels are low and/or high due to seasonal weather and climate changes.br6. Outdoor amenities, including furniture, watercraft and firepit are not available between October 15 - May 15.

Bed

Bath

Sleeps

$500.16

/ Nightly

Private Vacation Home

Bluff`s Charm 3 bedroom lake home on Keuka Lake

Penn Yan, New York, United States

Bluff s Charm is a cozy 3 bedroom home on Keuka Lake's east side, in the East Bluff neighborhood, just minutes from the Village of Penn Yan.brbr *170 of private beach on Keuka Lakebr *Wooded settingbr *Cabana on the lakefront with attached deck and dockbr *Large wrap around deckbr *Canoe and kayaks available for guest usebrbrBluff s Charm is a one story home with a large wrap around deck, a wonderful place to sit and watch the water, catch sunrises/sunsets, or do some bird watching. The house sits down from the main road, tucked in the trees, and is accessed, from the parking area, by several flights of stairs.brbrThe main living area has windows overlooking the lake, with a fully stocked kitchen, comfortable living room and dining area.brThere are 3 bedrooms, one with a King bed, another with a Queen bed, and a third with a Twin over Queen bunk bed. The home has 2 full baths, both with tub/showers.brbrThe outdoor deck wraps around two sides of the house, and there are several flights of stairs to the lakefront. The lakefront cabana is a great spot to relax and get out of the sun for a few minutes. On the beach area outside of the cabana, you ll find a firepit on the lake shore and a deck area with outdoor furniture.brbrThe pebble beach area extends along the shoreline and there is a private permanent dock for guest use, along with a kayak and a canoe. With over 150 of private shoreline/lakefront, Bluff s Charm is an absolute gem for privacy on the lake during your vacation and plenty of room to enjoy the lake.brbr*Air conditioning is provided via wall unitsbr*A limited amount of paper towel, toilet paper, soaps, is provided for each guest.brbr**We ask that the primary renter be over the age of 25. By booking you agree with this policy and comply with this requestbr**No pets or animals allowedbr**No parties allowedbr**Smoking prohibited.br**Guest must comply with maximum occupancy at all times. No Exceptions. Only 7 guests allowed at any time.br**Parking for 3 vehicles only.br**Lake conditions are not guaranteed and are non refundablebr**Guests are asked to initial a rental waiver, sent via email, immediately after bookingbrbr**DOCK USEAGE:brA permanent dock is provided, you are solely responsible for ensuring docks, and/or mooring facilities are adequate if guest brings or rents watercraft/boat.brGuest assumes all liability for use of the dock and assumes responsibility and liability for damages done to the dock, or their boat, during their stay.... whether the damage is done by their watercraft or the guest themselves.br**Seasonal amenities: kayaks and some outdoor furniture are available seasonally and are available for use from mid-May to October

Bed

Bath

Sleeps

$849.33

/ Nightly

Private Vacation Home

Keuka Lake view! Welcome to CASA DEL LAGO UNIT # 38

Penn Yan, New York, United States

WELCOME to CASA DEL LAGO (UNIT 38), the Lake House on Keuka! BRAND NEW -SLEEPS 11 Guests with amazing lake views and just steps from the water, directly across the street you will find a marina and public beach with lifeguards, picnic areas and playground for your enjoyment. This unique property is a duplex with completely separate entrances but may be joined through outdoor living space to host larger gatherings. (Rent both units-sleeps 22). If interested in booking UNIT 40, Please SEARCH for property # 3347784.brWhether it be for couple’s or friends get-a-way or a family vacation, this home is perfect for those intimate gatherings and great opportunities for making memories of a life time. This home is one of a kind, as it offers Guests the choice of renting the entire home (sleeps 22) for extended family/friend gatherings or for smaller groups you have the option of renting one of the two units (sleeps 11). Guests have the option of complete privacy, with separate entrances, for either unit or adjoining households thru the main living space’s covered outdoor deck for larger parties. brbrBuilt in March 2023, this property offers all the modern day conveniences with the comforts of home. Each unit offers a fully stocked gourmet kitchen (any chefs’ dream!) as well as a dry bar to enjoy your favorite spirits from all the amazing wineries and breweries from around the area. The home is equipped with High Speed Internet along with Smart TV's in the living room and all three bedrooms with premium movies to choose from. Nestled in the heart of the Finger Lakes this gorgeous property offers a large lot with park like grounds, plenty of trees for shade and ambiance to enjoy roasting marshmallows by the campfire. This three story home is conveniently located and walking distance to many of the shops, restaurants and other amenities Penn Yan Village has to offer. Casa Del Lago provides amazing outdoor space as well, whether taking in some sun on the private upper deck (off the Master Suite) or enjoying the incredible outdoor space while dining under the covered deck (off the main living space) in rain or shine! This property (and photos) speaks for itself!

3

Bed

3

Bath

11

Sleeps

$592.23

/ Nightly

Private Vacation Home

Luxury Lake House, Dock, Firepit, Lake Access

Penn Yan, New York, United States

Summary:brbrExperience luxury living on the coveted Keuka Lake East Bluff in Penn Yan. This expertly designed modern retreat offers panoramic lake views from every bedroom, including a stunning primary suite with private deck access.brbrbrbrPerfect for family vacations, wine weekends, boating trips with a large enough dock to hold 2-3 boats, and group getaways. Minutes to wineries, downtown Penn Yan, and lake access.brbrbrbrModern. Spacious. Designed to gather.brbrbrbrGuest Access:brbrPrivate entrance, parking and garagebrbrbrbrThe Neighborhood:brbrLocated in the heart of Kueka Lake with lake access, a private dock, and plenty of parking. Close proximity to all the best Keuka Lake has to offer.

Bed

Bath

Sleeps

$298.75

/ Nightly

Private Vacation Home

Grand Luxury Escape In The Heart Of Finger Lakes Wine Country

Penn Yan, New York, United States

This is a large super unique and luxurious property nestled on a peaceful wooded landscape. Fields surround the gravel drive down to the walkway and its not uncommon to spot deer, rabbits, and many birds along the way. The illuminated walkway brings you to the house which is surrounded by a rambling brook/stream on both sides. A large wood deck is the perfect place to sit out and enjoy the sounds of nature.brThe house has three levels and has a open spacious floor plan. The kitchen has all modern conveniences including GE Profile Stainless Steel appliances and granite counter tops. There is Wi-Fi .The laundry room features front loading washer/dryer. Dining room has a large table and seating for eight. The mid level bedrooms (one queen bed, one full) each have a full bath. The half bath is in the laundry room, off the kitchen. The bottom level is a huge room with a walk out and fireplace and a queen bed. The back of the house features a 'glass room' with a futon that could sleep one or two more people. There are three full size couches that could easily sleep three more. It is a long walk to the door down a deck. It is NOT steep, but there aren't handrails until the bottom section. We recommend to bring your own drinking water as this home is on a well/septic system.

3

Bed

2

Bath

8

Sleeps

$1325.36

/ Nightly

Private Vacation Home

Memory Lane: An Unforgettable Family Retreat!

Penn Yan, New York, United States

Gather your favorite people and create unforgettable moments at Memory Lane, a stunning eight-bedroom, five-and-a-half-bath lakefront retreat on Keuka Lake. Perfect for family reunions, wine trail adventures, or group getaways, this spacious three-level home offers everything you need for a comfortable and memorable stay in the heart of the Finger Lakes.brbrThe main level welcomes you with an open floor plan designed for connection. A fully equipped kitchen makes it easy to cook for a crowd, while the expansive dining and living areas open to a beautiful wrap-around porch overlooking the lake—perfect for sipping morning coffee or enjoying an evening glass of local wine. The main floor also features a serene primary suite with a king bed, private bath, and stunning lake views.brbrUpstairs, three additional bedrooms offer cozy accommodations and plenty of natural light. The lower level adds even more space with a comfortable family room, two lakefront master suites with ensuite baths, and two more bedrooms ideal for kids or larger groups.brbrStep outside to enjoy 136 feet of natural lakefront, where gentle waters make swimming and paddling fun for all ages. Relax on the deck, launch a kayak, or tie up your boat at the seasonal dock. With Morgan Marine, Red Jacket Park, and Top of the Lake Restaurant all within walking distance, you'll have everything you need for the perfect lakeside escape.brbrLocated just a mile from Penn Yan and right on the Keuka Lake Wine Trail, Memory Lane puts wineries, restaurants, and local attractions at your fingertips. Whether you're here to unwind or explore, this exceptional home blends modern comfort with the simple joy of lake life—where every stay becomes a cherished memory.brbrOccupancy: This property is closely monitored for responsible renting. The maximum occupancy of each home is the number of guests allowed on the premises at any given time. This includes both day and overnight guests as well as all children including infants.brbrNote: br1. You will receive an email upon confirmation with a link to our Guest License Agreement which is a copy of our Rental Rules that must be signed and returned within 7 days of receiving. br2. Smoking is not allowed in any rental property. This includes vaping and e-cigarettes. br3. Homes are not handicap accessible, unless stated in the description.br4. Air conditioning is not available unless listed as an amenity. If available, air conditioning is considered a seasonal amenity and is only available May 15 - October 15.br5. Homes are not guaranteed allergen-free, even those that do not allow pets.br6. Docking is not guaranteed if water levels are low and/or high due to seasonal weather and climate changes.br7. Outdoor amenities, including furniture, watercraft, and firepit are not available between October 15 - May 15.br8. 1 dog under 30 lbs allowed maximum and $100 plus tax non-refundable pet fee applies.

8

Bed

5

Bath

20

Sleeps

$983.91

/ Nightly

Private Vacation Home

Brandy Bay Serenity: Truly a One-of-a-Kind Retreat!

Penn Yan, New York, United States

Located in beautiful Brandy Bay—one of Keuka Lake's most desirable destinations—Brandy Bay Serenity combines modern comfort with classic lakeside charm. With over 120 feet of gradual lake frontage, this spacious, contemporary home is ideal for family vacations, group getaways, or a relaxing week by the water.brbrInside, you'll find warm, inviting décor and an open layout designed for connection and comfort. The entry level features a serene master suite with a queen bed, gas fireplace, and flat-screen TV. Across the hall, a full bath adds convenience. The fully equipped chef's kitchen offers stainless steel appliances, granite countertops, and plenty of counter space, while the large dining area overlooks Keuka Lake through picture windows.brbrThe open living room includes a vaulted ceiling, cozy gas fireplace, and queen sleeper sofa—perfect for movie nights or morning coffee with a view. Step outside onto the spacious, partially covered deck that wraps around the home and offers outdoor dining space and panoramic lake views.brbrUpstairs, the semi-private loft includes a king bed, queen bed, two twin beds, and a second full bath—ideal for families or larger groups.brbrOn the lower level, the recreation room provides extra living space with sleeper sofas, a TV, and direct access to the patio and fire pit area. You'll also find a second bedroom with a queen bed and crib, a full bathroom, and a laundry room with a second refrigerator for drinks and snacks.brbrOutside, enjoy the large yard, outdoor seating, and private dock with over 120 feet of natural lake frontage. The level shoreline is perfect for swimming, paddleboarding, or simply relaxing in the sun.brbrConveniently located less than half a mile from Keuka College and just minutes from Penn Yan, you'll have easy access to local dining, shops, and wineries on both the Keuka and Seneca Lake Wine Trails. Don't miss the Windmill Farm and Craft Market for local goods and handmade treasures.brbrWhether you're gathering for a family reunion, a weekend with friends, or a quiet lakeside escape, Brandy Bay Serenity offers everything you need for a luxurious and memorable stay on Keuka Lake.brbr*Note: Your safety matters to us. This property is equipped with exterior security cameras. The cameras do not face any interior living spaces. brbrOccupancy: This property is closely monitored for responsible renting. The maximum occupancy of each home is the number of guests allowed on the premises at any given time. This includes both day and overnight guests. brbrNote: br1. Smoking is not allowed in any rental property. This includes vaping and e-cigarettes. br2. Homes are not handicap accessible, unless stated in the description.br3. Air conditioning is not available unless listed as an amenity. If available, air conditioning is considered a seasonal amenity and is only available May 15 - October 15.br4. Where pets are allowed it is indicated. Otherwise, pets are not allowed. Homes are not guaranteed allergen-free, even those that do not allow pets.br5. Docking capabilities may vary based on current water levels. Docking is not guaranteed if water levels are low and/or high due to seasonal weather and climate changes.br6. Outdoor amenities, including furniture, watercraft and firepit are not available between October 15 - May 15.

Bed

Bath

Sleeps

$700.0

/ Nightly

Private Vacation Home

Private, Level, Beachfront Cottage; No Stairs To Beach!

Penn Yan, New York, United States

Situated on the East side of beautiful Keuka Lake, our large, level, private beach is perfect for swimming, sunbathing, boating and relaxing! Our cottage is 5 miles from shops and restaurants in Penn Yan and a 15 minute drive from Hammondsport, which was recently named 'America's Coolest Small Town'!brbrWe are within walking distance of Rooster Hill Winery and a short drive from at least 15-20 of the best wineries in the Finger Lakes!brbrOur cottage is located on a quiet point on East Lake Road, which is perfect for walking, running, biking and strolling! brbrCottage completely painted and re-carpeted in Fall 2024-Early Winter 2025! Back patio floor resurfaced Fall 2024!brbrOur three kids have spent their summers on this lovely, quiet and serene point. It is truly the perfect spot for a family vacation or adult getaway.brbrAmenities Include:brWiFibrCablebrTVbrOff street parkingbr2 twin bedsbr1 queen bedbr1 queen bedbr1 twin/queen convertible bed on front sleeping porch.brEach bedroom includes: at least 1 bed, 1 dresser and 1 closet brFull kitchenbr2 Full baths brCooking utensilsbrMicrowavebrOvenbrRefrigeratorbrBed linens providedbrGames, toys & booksbrGas grillbrFire pitbrRow boat + four adult life jacketsbr20 foot dock brOutdoor furniturebrPicnic tablebrScreened-in back porch with large table and chairsbrClothesline (2)brAmple parking - drive up to side door to unloadbrLarge, level yard great for playing and sunbathing!

Bed

Bath

Sleeps

$720.47

/ Nightly

Private Vacation Home

Charming lake view home w/dock, pergola and grill & lake side fire pit

Penn Yan, New York, United States

The OverseebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrRelax with family and friends at Oversee, an enchanting two-story lakefront cottage on one of Western New York's most scenic gems—Keuka Lake, part of the world-famous Finger Lakes region. Whether you're sipping local wine on the dock or cozying up indoors with lakeside views, this five-bedroom, two-bathroom home offers a stunning, year-round getaway in the heart of wine country.brbrWake up to breathtaking sunrises over the water, then head across the quiet lake road to enjoy your own private waterfront oasis. Down 30 steps from the house lies 50 feet of private lake frontage, complete with a dock perfect for lounging, fishing, or jumping into the clear 4–5-foot-deep waters for a swim. Bring your kayak or rent a boat to fully immerse yourself in lake life. A picnic table by the beach invites lazy lunches. A waterproof storage trunk holds many folding chairs to be used at the lakefront fire pit for unforgettable evenings filled with stargazing and s’mores.brbrBack at the house, the backyard's peaceful pergola offers a shady retreat where you can sip a glass of Finger Lakes wine, share stories over dinner, or curl up with a good book. A gas grill is available for outdoor cooking, and the flat lawn area behind the house is ideal for lawn games and family fun.brbrInside, Oversee features modern comfort in a charming lakeside setting. The home includes three queen beds, one full-size bed, and a bunk room with two twin beds and an additional full—a perfect setup for multigenerational families or groups of friends. Every bedroom has its own split-unit air conditioner/heat for customized comfort through all seasons. A fully equipped kitchen makes mealtime easy, and a spacious dining table ensures everyone has a seat. The cozy living room includes ample seating and a wall of windows facing the lake, making it a welcoming space for board games and movie nights during cooler months.brbrOversee is just 15 minutes from Downtown Penn Yan, where you’ll find charming boutiques, local restaurants, and even a historic movie theater. The area is bursting with things to do in every season: touring the Keuka Lake Wine Trail, exploring Watkins Glen State Park’s stunning waterfalls and hiking trails, or renting bikes to cruise the Keuka Lake Outlet Trail. Fall is rich with vibrant foliage and harvest festivals, while winter invites cozy wine tastings, snowshoe adventures, and nearby skiing at Bristol Mountain. Spring brings blossoming vineyards, local farmers markets, and peaceful lake views before the busy summer months.brbrNo matter the time of year, Oversee offers a perfect balance of tranquility, recreation, and Finger Lakes charm. Come experience the beauty of upstate New York and make lasting memories at your home away from home.brbrThings to KnowbrVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrParking notes: There is free parking available for 4 vehicles.brbrSecurity camera details: Pointed outward at driveway.brbrDock details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

5

Bed

2

Bath

12

Sleeps

Vacation Home Rentals By Owner In Penn Yan, NY

$1318.34

$381.66

$281.7

$324.67

$210.72

$459.2

$265.65

$346.04

$310.2

$1053.22

$1480.21

$1168.4

$500.16

$849.33

$592.23

$298.75

$1325.36

$983.91

$700.0

$720.47

Rent a place that suits your needs

Most popular vacation rentals in Penn Yan

$1421.33

$1047.12

$1074.37

$1076.93

$1086.67

$1168.00

$1174.88

$2632.00

$2146.67

$1640.14

Most Popular Cities in New York