Family-friendly holiday rentals in Penn Yan

Sunset Paradise Cottage

Welcome to "Sunset Paradise”! A 4 bedroom, 2 bath picturesque lakefront cottage located on the eastern shore of Cayuga Lake in the heart of the beautiful Finger Lakes region of New York State. This property features a fully screened in porch, upper and lower decks, a relaxing 6-person hot tub, a private dock with a large sun deck, 1 boat lift, & 1 PWC lift. Fish off the dock, float on a tube (we can rent ours!), relax in the oversized hammock or enjoy a paddle in the 2 kayaks provided for use.

On Lake, Stunning Views, Sunrises, Pet Friendly!

We are right on the lake! The view is amazing and the atmosphere is serene and relaxing. Conveniently located. The fully stocked cottage is comfortable and offers a homey feel - clean, updated. Gas fireplace offers additional warmth & ambiance. Fabulous deck with amazing views! Dock/beach area with fire pit. Master bedroom - watch the sunrise right from bed! Kitchen is fully stocked, seating for 6, laundry and two bathrooms. Plenty of parking and a lovely private yard. Linens included

Burdett Home with a View. Perfect location.

Walking distance to Grist Iron, JR Dill and Two Goats Brewing. 6 miles from downtown Watkins Glen which offers boat launches, beach, kayak rentals and many other things. Very Clean. Parking for 6 cars. Large carport. Central air. Large, well equipped kitchen including Keurig and cone filter coffee makers, ice maker, blender, toaster oven, dishwasher. Large shower and closet in master bath. Bathtub in second bath. Hot Tub and fire pit. High speed/wireless internet , DVD player. 3 TV's.

Private Floor on Cayuga Lake Shore

Private ground floor contains two bedrooms (queen and twin XL beds), bathroom, and family room. Family room has sofa bed, TV, internet, ice machine, kitchenette, bottled water dispenser, and refrigerator. Several steps from Cayuga Lake in the middle of the Cayuga Wine Trail. Very close to wineries, cideries, distillery, and beer garden. Lakefront (shared with owner) includes a propane grill, picnic table, kayaks, and dock for fishing or swimming. Easy walk down beach for children.

Year Round Blue Star Cayuga Lakefront House

Welcome to our spacious updated 3 bedroom home with two full bathrooms and one half baths. On Cayuga Lake,it is perfect for family vacations or couples looking to get away. Swimming, fishing, kayaking, leaf watching, star gazing, ice skating, ice fishing, this is a year round destination. Beautiful modern kitchen and a great big deck off the house and dock for warmer weather. Great location for wine and beer trails as well as woman’s museum. No additional cleaning fee! NO PARTIES!

Hook, Wine and Sinker

Completely updated in 2022! Canandaigua lakefront 5 minutes outside of Naples, NY! Level lakefront- Stunning views of South Hill- perfect for autumn leaf gazing and also summertime swims off the permanent dock. With kayak, inflatable toys, gas BBQ, WiFi, cable TV & electric awning over a picnic table. Enjoy s’mores over the campfire pit. Tastefully decorated, well equipped kitchen, washer/dryer & bedroom AC. Escape to the vineyards, Bristol Mtn. & all the Finger Lakes has to offer!

Comfort and Luxury- Keuka Lake Dream Property

You must see the finest Keuka style home, and experience the life...Sleeps 4 in two separate bedrooms (one king bed - one queen) - and a full size bed for 2 additional people in the ladder accessible loft area. Need more space? Check out the house next door (Finger Lakes Most Welcome Home) (sleeps 8 in three separate bedrooms - plus one bath, kitchen. living room and covered deck) Sparkling hot tub is emptied & sanitized prior to your arrival.

Keuka Lake Overlook & Dock @ Splitrock

Wonderful vacation rental for families or couples, lots of space indoor & out. Lake view with lake access (across the road-600ft). Pontoon boat tours & rentals available for guests ! Located on the Keuka Lake Wine Trail! Close to Hammondsport, Penn Yan & Watkins Glen. Only 7 miles from the quaint village of Hammondsport, that offers a local grocery store, small shops, and restaurants. Message me for seasonal discounts!

Water’s Edge • Lakefront w/ Kayaks, Fire Pit & Doc

Water’s Edge is a lakefront retreat perfect for families, couples, or friends traveling together. Spend your days kayaking, wine touring, grilling, and swimming—then unwind by the fire or stargaze from the dock. With two private living areas and unbeatable lake views, it’s the ideal setup for shared adventures and personal space.