
Vacation rentals in Odessa
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Top-rated vacation rentals in Odessa
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Hilltop hideway for nature lovers w/3 waterfalls.
4 BR 3 BATH home. Relax, restore, rejuvenate or unwind at 1 of a kind retreat in the heart of the Finger Lakes! Perfectly situated on 20 acres, landscaped, surrounded by woods & waterfalls. Enjoy a glass of wine/drink & dine on the large patio while taking in the view of the surrounding vistas. May also view from inside from picture window in living and dining rms. Many types of wildlife visit! NO PETS ALLOWED. No late ck/outs unless arranged with host. Violations will incur fee of $75/ hr.
4.98 out of 5 average rating, 163 reviews
Catharine Valley Place * 4 miles from Watkins Glen
Come stay at Catharine Valley Place, a comfortable ranch style home on 1.2 acres, with an expansive, grassy backyard and a trail through the woods leading to Catharine Creek. Those who will enjoy this full house rental the most are 2 to 3 couples, families, or up to 6 friends vacationing together. Conveniently located just 4 miles from downtown Watkins Glen, there are places to explore in all directions. Make Catharine Valley Place your home base after a busy day of exploring the Finger Lakes!
4.99 out of 5 average rating, 170 reviews
Close to Watkins Glen. House w/ hot tub+game room
Bring your friends to the Finger Lakes. Lots of room for fun, 3-4 couples easily can enjoy their stay in our spacious house with large hot tub. 2 night minimum stay. Gather with friends or family. Enjoy hiking, wineries, and breweries. Go swim at Seneca Lake Park, a splash pad, ice skating or relaxing after a day at the Watkins Glen races. Just 30 minute drive away from Watkins Glen is Corning Museum of Glass, Cornell University, or Ithaca College. Plenty of places to shop, dine and more!
4.9 out of 5 average rating, 111 reviews
Finger Lakes Dropstar on Cayuta LAKEFRONT
Dropstar is a modern spacious 3300 square foot retreat in a peaceful setting on Cayuta Lake in the breathtaking NY Finger Lakes region. Immerse yourself in nature and see the best views of the entire lake through the enormous windows, sunbathing on private decks, fireside on the patio or fishing and swimming on the dock at Dropstar. Grill or cook for a crowd in the fully stocked gourmet kitchen, rest privately in 4 large appointed bedrooms and never wait with 3 full baths. LIVE, LOVE, LAKE!
4.95 out of 5 average rating, 142 reviews
Artsy Fartsy Cabin
Relax in this heated cozy 12x12 cottage nestled in the woods. Complete with a full size bed, table for two, and kitchenette to make the late night hot chocolate or tea, and those tranquil morning coffees. Enjoy relaxing on the 6x12 screened in porch or around a warm fire pit. The shared restroom and shower house aprox 5 minute walk. Only minutes from Watkins Glen, Seneca Lake, wineries, breweries, and distilleries, and a multitude of waterfall and hiking trails. PLEASE READ other details.
4.93 out of 5 average rating, 107 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.
4.96 out of 5 average rating, 217 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.
4.98 out of 5 average rating, 290 reviews
1875 Renovated Schoolhouse with an Igloo!
Explore the Finger Lakes and make this renovated schoolhouse with an outdoor igloo as your basecamp. Nestled in the countryside, you'll find absolutely stunning views with surroundings that are peaceful and quiet. A perfect escape for couples and friends that is dog-friendly too, you're within minutes of the Seneca Lake Wine Trail, the gorgeous Watkins Glen State Park, and the renowned WG International Racetrack. Want to simply relax at the FLX Schoolhouse? It's the perfect for that too!
4.95 out of 5 average rating, 428 reviews
Lake Spirit-Lakefront-Hot tub-Pet friendly-Boats
Lake Spirit welcomes you & your pets year-round! This lakeside home provides a retreat-like experience, offering activities for every season. You can fish, ice fish, relax in the hot tub, enjoy the two decks and docks, the boats or explore the Finger Lakes region. Amenities include a Hot tub, BBQ, fireplace, fire pit, books, games, kayaks, canoe, and pedal boat. While off the beaten path, the property is conveniently located near renowned gorges, waterfalls, vineyards, and distilleries.
4.84 out of 5 average rating, 143 reviews
Catharine Cottages (#1 Seneca)
Find luxury inside and nature outside. Cottage 1 has a double bed in one corner, a trundle bed in the opposite corner and a private bath. Additionally find a mini fridge, a microwave, a coffee maker with coffee/tea supplied. We offer a welcome basket with oatmeal, muffins, popcorn, nuts, local cheese & jam, and fruit. Outside there is a covered porch with rockers and a picnic table with a private fire pit and charcoal grill. We supply firewood ($4 a bucket) and charcoal (free).
4.96 out of 5 average rating, 102 reviews
Queen Catherine Apartment Suite
The Roost is comprised of 3 private apartments all on the 2nd floor of our downtown building. The Catherine suite is a curated two bedroom apartment, full of vintage finds and cozy amenities. Just blocks from Shequaga Falls, a stunning cascade right downtown. As you walk this small town main street you will find basic necessities, including brews and coffee. Montour Falls is central to all that the Finger Lakes has to offer, and minutes from Watkins Glen.
4.9 out of 5 average rating, 264 reviews
Speedway Suite
We offer a private studio off of a family home. You enter through a shared breezeway, which gives access to a large shared backyard with plenty of opportunity for privacy. We are located just minutes from breweries and waterfalls. The wine trail starts just 12 minutes away and Watkins International is a 15 minute drive. Let us host you and help make this trip one to remember!
4.98 out of 5 average rating, 121 reviewsPopular amenities for Odessa vacation rentals
Other great vacation rentals in Odessa

Cozy Finger Lakes Cabin, Hot Tub Oasis
4.9 out of 5 average rating, 127 reviews
Namastay in Our Cozy Loft Style Apartment
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Private Modern Farmhouse
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The country escape space
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FLX Watkins Glen, Hiking, Wine Country, Waterfalls
4.98 out of 5 average rating, 60 reviews
The Honey Hut
5.0 out of 5 average rating, 50 reviews
Watkins Glen Luxury Escape on Seneca Wine Trail
5.0 out of 5 average rating, 97 reviews
Winery Nook at Osmote
5.0 out of 5 average rating, 25 reviewsDestinations to explore
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- Cornell University
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- Bristol Mountain
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- Cascadilla Gorge Trail
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