Holiday houses in Odessa

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Top-rated holiday rentals in Odessa

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Top Guest favourite
Tiny home in Burdett
4.99 out of 5 average rating, 145 reviews

FLX 1-Lake View Tiny Cabin

Nestled up on a hill overlooking Seneca Lake, watch the sunset while laying in bed or from your own patio with a fire crackling. We are local hosts and will make sure you have an unforgettable stay! Everything you could want to do in the Finger Lakes will be at your fingertips. Wineries galore, two even just next door, multiple breweries nearby, minutes to the lake, 15 minutes to downtown Watkins Glen, 10 minutes to hiking trails at the national forest, or stay in, relax, and enjoy the view!!

Top Guest favourite
A green roof features a weather vane shaped like a dog, positioned atop the building. The background reveals a serene view of Seneca Lake under a clear blue sky, with lush greenery framing the scenery.
Apartment in Hector
4.92 out of 5 average rating, 358 reviews

Private Year-round Lakefront on Seneca Wine Trail

You’ll enter a Large, Luxurious, Private studio apartment in beautiful Arts & Crafts style. *Located on a Town Maintained secluded lake-side road on the shores of the east side of Seneca Lake. *Ten-foot Coffered Ceilings *On the Seneca Lake Wine Trail. *We welcome visitors all year round. A wonderful option for couples looking for a private, quiet place to get away. *Many custom-crafted details. *2 additional guests can be accommodated with a fold-out sofa bed (an additional fee. )

Top Guest favourite
A simple exterior view of the tiny house is captured, featuring a metal roof and a garage door. A small lawn area with green grass and two outdoor chairs is present, along with a black barbecue grill. Trees are visible in the background.
Tiny home in Cayuta
4.96 out of 5 average rating, 166 reviews

House on the Hill

A tiny house with the comforts of home. Single Bedroom stair free in-law suite with amazing sunsets and the feeling of being in the middle of the woods while still being close enough to enjoy a reasonable drive to some of the Finger Lakes best hiking trails, food, wineries and other destination locations. If you come in the winter you will want an all wheel drive vehicle if there is snow on the roads, but half a mile down the hill and you are on the state highway to the finger lakes region.

Top Guest favourite
A tiny home is set amid trees and a gravel path. A front porch with steps leads to the entrance. A propane grill is visible to the side, with a storage shed in the background. Natural surroundings provide a serene backdrop.
Guesthouse in Montour Falls
4.95 out of 5 average rating, 223 reviews

Kim’s Country Retreat/Catharine Valley Trail

Sweet tiny home located beside my home. Enjoy the privacy & the wildlife while remaining close to all the great attractions Watkins Glen & surrounding areas has to offer. The night skies are beautiful from the front porch. Satellite Internet with Roku TV in the living room & bedroom. One mile to She-Qua-Ga Falls. A short drive to Watkins Glen Lakeside Park (4.5 Miles) , W.G Race Track (5.2 Miles), Watkins Glen Gorge Trail (3.4 Miles) & many more great wineries and shops. Pet allowed w/fee.

Top Guest favourite
An inviting a-frame cabin is surrounded by a snowy landscape, with evergreen trees in the background. Ski equipment is propped against the front, and a wooden sled rests nearby in the snow. A festive wreath adorns the door, adding a touch of seasonal charm.
Tiny home in Odessa
4.98 out of 5 average rating, 103 reviews

Adventure Awaits A-Frame

Take a break and unwind at Harpy Hollow in this cozy 12x16 a-frame cabin. Nestled in the forest of wine country, there’s plenty of adventures just waiting for you! From hiking to biking, breweries, wineries, distilleries, or just relaxing by the fire. You will find a comfortable place to relax after a long day of making memories. The cabin has a full size bed with all of the linens. The shared restroom and shower are only a short walk from the cabin. Please read property and other details.

Top Guest favourite
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.
Home in Burdett
4.98 out of 5 average rating, 234 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
A view of the interior showcasing a cozy living area with a gray chair and side table, complemented by a blue area rug. A kitchenette with a mini-fridge, sink, and stovetop is visible to the left, while a bright bathroom is accessible straight ahead, with a glimpse of the bedroom beyond.
Place to stay in Watkins Glen
4.94 out of 5 average rating, 194 reviews

Boat House/Fish Room-Seneca Canal,Watkins Glen

Boathouse experience on the Seneca Canal in Watkins Glen, NY. Private 1st floor self contained unit (new in 2021) in the boathouse over looking Seneca Canal. Access to shared laundry, common entertaining areas, grill,. The unit entrance is from your private dock overlooking the canal. Plenty of room to park. Dog friendly. Other listings are Anchor Room and Wheel Room. NOTE - this is a our smallest unit and is most suitable for a solo traveler or couple sharing the double bed.

Guest favourite
An aerial view captures a spacious living and dining area with elegant furnishings. A large window allows natural light to illuminate the room, featuring a wooden dining table, comfortable seating in shades of gray, and decorative accents such as plants and artwork.
Home in Watkins Glen
4.9 out of 5 average rating, 109 reviews

4BR w/ Game room & just min. from WGI & Wine Trail

The whole group will enjoy easy access to everything from this centrally located place. Equipped w 4 large bedrooms, 2 Living rooms & a very unique game room. You will have plenty of space stretch your legs. The 4-acre grounds make for peace & privacy. Head outside on the large deck to enjoy the fresh air and do some grilling. This beautifully decorated home comes equipped with plenty of amenities. If you have a larger group, book our sister property next door too, Gracie's House.

Guest favourite
Guest suite in Corning
4.96 out of 5 average rating, 204 reviews

No. 3537 Light & Airy Cozy Loft

Serene Cozy Loft on acreage •High-Speed WIFI• Our towns little slice of Heaven ✨ 625 sqft Unlimited parking Less than 2 miles to Downtown Corning & few miles from Fingerlakes & Wineries Electronic fireplace Picture frame TV Sleeps 4, queen bed & Sofa Sleeper Washer & Dryer Childproof cabinets Great views, Peaceful & relaxing No cats Outdoor wood & propane fire pit Patio furniture Venue on premise an acre away! If you’re able to book, there will be no wedding during your stay.

Guest favourite
Apartment in Montour Falls
4.88 out of 5 average rating, 175 reviews

A Timeless Stay by the Falls | *Winter Specials*

2nd Floor Apartment in a divided Victorian. This 1880’s home has been updated and renovated to blend historic charm with modern comforts. The apartment includes a spacious living room with a 75” television. An updated galley kitchen, fully stocked for short or long term stays. Two stylish bedrooms with Queen Beds, and a large full bath with washer/dryer. Come stay close to everything, in the quiet charm of the Historic District, all within steps of the magical She-Qua-Ga Waterfall.

Top Guest favourite
A cozy bedroom featuring a queen size bed dressed in gray linens. Artwork is displayed on the walls, and a bedside lamp provides soft lighting. Natural light filters through a window, framed by patterned curtains, while an air-conditioning unit is positioned nearby.
Apartment in Watkins Glen
4.99 out of 5 average rating, 142 reviews

"The Loft" 2nd story apt. 2 mi. from Watkins Glen!

Private, new build. Full kitchen, dishwasher, full fridge. Village water. stackable washer/dryer. Off street parking. Free internet, smart TV in bedroom & livingroom. Queen size bed. Heat and air-conditioning. 2.9 mi from historic Watkins Glen International. 2 mi from down-town Watkins glen. Enjoy the beautiful finger lakes Wine trail, the Watkins Glen State park, Seneca Lake, WGI, and all that the finger lakes has to offer with a cozy place to land at the end of the day.

Top Guest favourite
A cozy cottage is set amidst greenery, featuring a wheelchair-accessible ramp leading to a wooden deck. A round table with an umbrella is positioned beside the deck, surrounded by a manicured lawn and tall trees in the background.
Cottage in Hammondsport
4.9 out of 5 average rating, 380 reviews

A Wise Getaway / Farm Cottage Near Keuka Lake

Welcome to 'A Wise Getaway' Amish-Built 800 Sq Ft Cottage on 50-Acre Farm – No Cleaning Fee! A peaceful retreat for couples, families & your four-legged friends Just 2 miles from Keuka Lake & minutes to the Village of Hammondsport, NY Minutes from wineries, breweries, NYS hunting land & Waneta / Lamoka Lakes ♿ Handicap accessible 🐾 $50 pet fee 🔥 Fire pit 📡 Wi-Fi 🍔 BBQ grill Top 5% rated Airbnb in region 20–30 mins to Watkins Glen, Penn Yan & Corning

Popular amenities for Odessa holiday rentals

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