Vacation rentals with a kayak in Milo

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Top-rated kayak rentals in Milo

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Top guest favorite

Home in Burdett

Waterfront Home with Sauna on Seneca Lake FLX

Unwind at Red Oak Retreat, a private waterfront home located in the heart of Finger Lakes wine country! This Seneca Lake escape features an expansive deck with magnificent sunset lake views, 100ft of lakeside lawn with a fire pit and kayaks. The property also boasts a two-story seasonal lakeside boathouse with bedroom and game area. Enjoy more than 15 vineyards within a 5 minute drive, with Watkins Glen State Park, "The Glen" Race Track, and Finger Lakes National Forest are only 15 minutes away.

4.99 out of 5 average rating, 119 reviews

Top guest favorite

Cabin in Penn Yan

Lakside log cabin w/ kayaks & firepit

Tree-top, lakeside log cabin in the heart of the Finger Lakes! - 3 bedrooms (2 kings, 1 queen) - 2 full baths -Stone fireplace w/ gas insert - Lake view & access - Canoe & 2 Kayaks - Stone fire pit - Screened in porch - Ping Pong Table - Washer/Dryer Central location on the west side of Seneca Lake Wine Trail. - 10 minutes from Penn Yan and Keuka Lake Trail - 15 minutes to Geneva - 20 minutes to Watkins Glenn - 1 mile from Keuka Outlet Trail - Walking or drive to Climbing Bines Brewery

4.91 out of 5 average rating, 213 reviews

Top guest favorite

A scenic view of Keuka Lake is captured from the deck, showcasing a spacious grassy area leading to the private lakefront dock. Boats are visible on the water, while the hillside is lined with trees under a clear blue sky.

Home in Hammondsport

*New* Keuka View/No Steps to lake*Sleeps 8/ kayaks

Delightful 4 bedroom, 3.5 bath lake house located on the Keuka Wine Trail. This comfortable home *SLEEPS 8 people and is just the right size for that perfect week or weekend on the lake. Enjoy gorgeous lake views from the many windows inside the home and outside on the newly built deck. This year round get-a-away sits on 75 feet of walk in level lake front. “Due Time” is the perfect home close to top-notch wineries, restaurants and all that this region has to offer. Strict *No Pets Policy.

4.96 out of 5 average rating, 137 reviews

Guest favorite

A spacious covered deck features multiple seating areas with blue cushions. A hot tub is present, alongside a coffee table and additional seating, all positioned to enjoy views of the lake. The deck leads to the lawn and dock area.

Home in Dundee

Spectacular Lake Views + Hot Tub: Winedown Oasis

Welcome to our beautiful lake house on Seneca Lake! The spacious lake level oasis has spectacular views and outdoor space! We offer all the indoor and outdoor amenities you desire on a vacation. Relax on the covered deck or in the sunken hot tub. Enjoy lots of patio seating with built-in kitchen, sink, and outdoor refrigerator. The dock, 100' of level lawn, and canoe and kayaks make this your best vacation yet. Come experience a lake week near all the best wineries and breweries in the region!

4.92 out of 5 average rating, 117 reviews

Top guest favorite

A view of a lakefront property illustrating a well-maintained yard with green grass and a dock extending into clear water. An American flag gently flutters near the house, while several outdoor chairs and loungers are arranged for relaxation. Lush trees form a backdrop against a clear sky.

Home in Dundee

Private Waterfront Home Wine Trail Hot Tub Dock

Welcome to Vineyard Views, your beautiful lakefront getaway! This year-round home on the FLX WINE TRAIL has 75' of LAKEFRONT and nice amenities. 3BR+sleeping loft/2BA+outdoor shower. The 4-SEASON covered PATIO/outdoor kitchen & dining enhances your experience any time of year! Enjoy the 4-person HOT TUB w/ TV. 60’ dock w/ electric BOAT LIFT, bar, seating area and fire pit. Steps to lake and ladder on dock. FAMILY VACATIONS, FRIENDS GATHERINGS and COUPLES GETAWAYS. Up to 2 dogs/$25 each/night.

4.98 out of 5 average rating, 160 reviews

Top guest favorite

A charming A-Frame cabin is surrounded by lush greenery, with a spacious deck featuring a dining set. The brown wooden steps lead to the entrance, while a winding gravel path connects to the serene outdoor space. Sunlight filters through the trees, adding warmth to the scene.

Cabin in Penn Yan

Seneca Lake A-Frame w/Stunning Views, Beach & Dock

Located in the heart of the Finger Lakes on the west side of Seneca Lake, this charming A-Frame cabin is perfect for a lakeside getaway. This open & airy retreat is in a desirable location right on the Seneca Lake wine trail. You'll enjoy sweeping panoramic views from any room in the house. Offering plenty of space to get comfortable in, some of our amenities include a large deck overlooking the lake, a beach cabana and a brand new dock. Relax, unwind and make yourself at home.

4.94 out of 5 average rating, 227 reviews

Top guest favorite

A serene lakeside view is depicted with four Adirondack chairs in varying colors positioned on a pebbled shore. A wooden dock extends into the water, surrounded by calm waves and lush green hills in the background, under a partly cloudy sky.

Chalet in Dundee

Private Keuka Lake-front Chalet | Stunning Views

This four-season get-a-away sits directly on the Keuka Lake Wine Trail and is ready for your weekend vineyard adventure. The 171' feet of private lakefront is the quintessential summer escape or fall foliage photo vista. The home features three bedrooms, two full bathrooms, and can easily sleep ten comfortably. The downstairs game room is designed with the kids in mind. The great room has a beautiful natural stone fireplace, perfect for relaxing after a great day on the Lake.

4.87 out of 5 average rating, 180 reviews

Top guest favorite

A private dock extends over calm waters, featuring a table and chairs shaded by a large umbrella. A kayak is positioned beside the dock, while the peaceful lake reflects the clouds above, creating a serene outdoor space for relaxation.

Cottage in Hector

Seneca Sunset Couple's Cottage

Kick back and relax in your own stylish, private lakefront cottage. You can enjoy spectacular views of Seneca Lake and her beautiful sunsets. You'll be located on the lake, just off of Rt 414, in a prime stretch of wineries, breweries, dining, hiking, local markets and live music. Your hosts, Stephanie & Kevin, are locals and appreciate what a unique experience this area provides. The neighborhood is secluded and quiet, with many local residents calling it home.

4.95 out of 5 average rating, 116 reviews

Top guest favorite

A serene lakeside home is positioned on a gently sloping green hill, featuring a spacious deck that overlooks the water. Surrounding trees provide a natural setting. The structure showcases large windows, allowing for abundant natural light and expansive views of the lake.

Home in Penn Yan

Beautiful Keuka Lake home close to Penn Yan.

Welcome to Keuka lake in this beautiful home that boasts 3 master suites. The living room has a panoramic view of Keuka Lake. There is a deck off the top floor and a patio off the first floor to sit and enjoy the lake view as well. From the downstairs patio you are only a few steps to the beach. At the end of the dock the lake is only 3 feet deep so it’s excellent for swimming. Everything in this house is new and very clean. We are a mile from downtown Penn Yan.

4.98 out of 5 average rating, 291 reviews

Top guest favorite

A bright living area features floor-to-ceiling windows offering views of the lake. A round dining table accommodates four, while a cozy seating arrangement includes a gray couch and two chairs. Natural light floods the space, enhanced by high vaulted ceilings and wood accents.

Home in Jerusalem

The Best Getaway on the Keuka Lake Wine Trail

Welcome to our “tree house" paradise on Keuka lake! It's one of the most unique cottages on Keuka. Our lake home promises you an unforgettable vacation on Keuka, with unparalleled views of the lake. Spend your days lounging on the beach, swimming, fishing, kayaking or tasting the local wine & cheese before you wind down on the hammock, taking in breathtaking views among the Keuka treetops. End each night with memories (and S’mores!) ‘round the campfire!

4.98 out of 5 average rating, 108 reviews

Guest favorite

A tranquil lakeside scene is presented at sunset, highlighting the calm water reflecting vibrant hues of orange and blue. Two docks are visible, framed by gentle silhouettes of trees, creating a peaceful atmosphere for relaxation.

Cottage in Penn Yan

Heart of the Fingerlakes Wine Country

Our special place sits upon 5 quiet acres on the majestic Seneca Lake. With the large wrap around porch, you will get lost in this beautiful setting while sipping on a glass of wine from many of our local Wineries. On the inside the first thing you will notice is the open floor plan, granite counter tops, and wall to wall windows with views for days. This property sleeps up to 6 guest, has 2 bedrooms up stairs and a large day room that can act as a 3rd.

4.91 out of 5 average rating, 170 reviews

Top guest favorite

A charming log cabin is set among lush trees, with sunlight filtering through the leaves. A stone pathway leads towards a lakeside picnic area, featuring a wooden table surrounded by nature. The tranquil waters of the lake are visible in the background.

Cabin in Hector

Little Lakefront Log Cabin on Seneca Lake

Welcome to our lovingly restored lakefront log cabin right in the heart of the Finger Lakes wine region! At just under 500sq/ft it's the perfect size for a cozy couple's getaway and ideally situated next to the region's best wineries, breweries and restaurants. Enjoy the private lakefront area with its deck, covered dock, and fire pit with multiple seating areas to enjoy perfect Seneca Lake sunsets.

4.99 out of 5 average rating, 103 reviews