House holiday rentals in Watkins Glen

4.99 out of 5 average rating, 100 reviews

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.

4.98 out of 5 average rating, 456 reviews

Charming home with Infrared Sauna & Hot Tub

The home is perfectly located. Explore wine country, local shops, the State Park with beautiful trails and gorges, Seneca Lake, and restaurants. Then come back and relax in your own private infrared sauna and NEW hot tub. Delicious local coffee, jam, truffles and eggs added to the listing. Please read "Where you'll be" section for additional information. TV-no cable. BED is a double vintage bed and is high up, step stools are provided. HALO (SALT) BOOTH AND HAND/FOOT DOMES-Additional fees.

The exterior of the guest house is displayed, featuring a covered parking area next to the entrance. Colorful flower beds with blooming tulips and greenery enhance the curb appeal. Two blue adirondack chairs are positioned on the porch, providing a welcoming spot for relaxation.

4.98 out of 5 average rating, 114 reviews

Watkins Glen Village, Walk to Gorge & Downtown

Welcome to Glenview Guest House! This gem is perfect for a single or couple looking for a private luxury space. A garden setting outside/artistic flare inside. Right in the heart of Watkins Glen, this beautiful home boasts a bright galley style kitchen, comfortable bedroom, snazzy bath & living room, complete with a workstation! There is rare village off street parking for your boat or race car! Outdoors: comfy sitting area, grill & fireplace with a view! A short drive to WGI & Lake Wineries.

4.96 out of 5 average rating, 148 reviews

A custom-built three-story home is set against a backdrop of autumn foliage. The exterior features large windows, a stone chimney, and a spacious deck. A paved driveway curves around the property, leading to a parked vehicle, adding to the tranquil environment.

Home in Beaver Dams

Hot tub• Copper Ridge Retreat• Sleeps 10 • Pool

Enjoy the Finger Lakes @ our custom built 3 story, 3 bedroom, 3 bath, open concept home! Built in 2015 by your Host, David. Relax in the 8 person hot tub & splash in the oversized heated pool w/diving board & bball hoop! Explore 70+ local wineries, state parks w/ waterfalls & trails. Only 6 miles from Watkins Glenn racetrack. About an Hour from 2 large Ski Resorts. Explore onsite the 70+ acres, sit around the campfire, play pick ball, pool, fooseball, arcade games, basketball & frisbee golf

Superhost

A wooden deck extends towards the lake, featuring a shaded seating area with a table and chairs. Surrounded by lush greenery, the cottage's exterior presents a blend of gray siding and large windows. Partial views of the lake are visible through the trees.

Home in Penn Yan

4.85 out of 5 average rating, 173 reviews

The Carlin Cottage on Keuka Lake

The Carlin Cottage sits on the private, beautiful, and picturesque East Bluff of Keuka Lake — it's the absolute perfect getaway for a couple, small group of friends, or a family! Our adorable cozy cottage sits right on the lake and has all you need for an amazing time — a fireplace, a sun porch overlooking the lake, a deck for lounging or outdoor meals, a bonfire pit, grill, kayak, and more! The lake also has amazing restaurants, wineries, and breweries all around, so you'll never get bored!

A spacious patio area is shown, featuring bright yellow Adirondack chairs overlooking a lush green lawn. A hot tub is positioned to the side, with expansive views of the water and trees in the background, under a clear blue sky.

4.97 out of 5 average rating, 440 reviews

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. Very Clean. Parking for 6 cars. Large carport. Central air. Large, well equipped kitchen including Keurig and basket 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. Generator on site.

An open-concept living area showcases a blend of modern and vintage styles. Stylish leather and fabric sofas are arranged on a soft area rug. A well-appointed kitchen is visible in the background, complemented by a large dining table, glowing pendant lights, and wood accents throughout.

4.98 out of 5 average rating, 207 reviews

1800s Post Office Turned Luxury Couples Getaway

Welcome to 1800 House, a post office turned modern vintage oasis, minutes from the Finger Lakes wine trail. With wide-plank floors, vintage art, a newly renovated chef's kitchen, this second floor home brims with romance and soul. Perfect for a couples getaway or vacation with friends, guests can relax in the clawfoot tub, sleep soundly in the plush, hotel-style bed, and explore the Finger Lakes wine trail. Experience old-world charm with modern luxury in this truly one-of-a-kind listing.

Guest favourite

4.96 out of 5 average rating, 392 reviews

1875 Renovated Schoolhouse in the Finger Lakes!

Explore the Finger Lakes and make this renovated schoolhouse as your basecamp. Nestled atop a hill on 2.5 acres, with absolutely stunning views with surroundings that are peaceful and private. A perfect escape for couples and friends, you're within minutes of the Seneca Lake Wine Trail, the famously gorgeous Watkins Glen State Park, and the renowned Watkins Glen International Racetrack. Want to simply relax and rejuvenate at the FLX Schoolhouse? It's the perfect retreat to do that too!

4.94 out of 5 average rating, 278 reviews

A tranquil lakeside view during fall showcases vibrant foliage, with trees in shades of orange, red, and yellow. Crisp leaves blanket the ground, while the calm water reflects the colorful landscape. A wooden dock is visible in the background, inviting relaxation by the lake.

Home in Keuka Park

Mutual Fun Keuka Memories

If you are going to just hang out, do it at this beautiful setting on Keuka Lake. Child-Friendly. Wonderful swimming area! Scenic drives around the vineyards. Spacious, comfortable home along a very quiet road. Cozy All-Season getaway! Enjoy your own private beach and dock. Swim/float/kayak in pristine waters. Walk along the lake. Stargaze. Campfires on the shore. Wintertime retreat. Brand new leather sofa, chair and ottoman. Nice, warm fireplace. Snuggle inside and let it snow!

A modern home with a light grey exterior is surrounded by lush greenery and several well-maintained, symmetrical Christmas trees. The property features a large, vibrant lawn, with trees offering a natural backdrop, enhancing the tranquil setting.

4.99 out of 5 average rating, 105 reviews

Luxury on Seneca Wine Trail, 3 King Beds and View

Welcome to Wineview Acres! This 24 acre former Christmas tree farm is complete with a newer 2000 sq. ft 3 bedroom home with amazing views and private waterfalls. Located at the start of the Seneca Wine Trail and just a short drive to the village of Watkins Glen, we are in the perfect location to enjoy the best of what the Finger Lakes can offer. If you prefer wine tasting, hiking, fishing, or a day at the race track you will be perfectly positioned to enjoy it all.

A steaming white cup sits on a wooden railing, overlooking a manicured green lawn. In the background, trees frame a colorful sunset, with hues of orange and yellow illuminating the sky. A circular stone firepit is visible on the grass.

4.98 out of 5 average rating, 141 reviews

The Sugar Shack (Pets stay free, NO added fees!)

Escape to this secluded 2-bedroom ranch in historic Watkins Glen, NY. Just 3 miles from town, it offers the perfect mix of privacy and convenience, surrounded by wineries, coffee shops, bars, and restaurants. Only 10 minutes from Watkins Glen International and next to the original Grand Prix road course, every drive feels scenic and special. With breathtaking views all around, this cozy retreat invites you to relax, explore, and savor the best of the Finger Lakes.

Guest favourite

A two-story house features a brown exterior with white trim. A spacious front porch is accessible by steps, surrounded by a small lawn and gravel landscaping. Several large windows provide natural light to the inviting entryway.