Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Dundee

4.98 out of 5 average rating, 121 reviews

Private Waterfront Home Wine Trail Hot Tub Dock

Welcome to Vineyard Views, your luxurious lakefront getaway! This year-round home on the Finger Lakes WINE TRAIL has 75' of LAKEFRONT, level yard, indoor-outdoor living & modern amenities. 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. Plenty of room inside & out for FAMILY VACATIONS, FRIENDS GATHERINGS and COUPLES GETAWAYS. Up to 2 dogs OK/night fee.

Guest favorite

A large A-frame home is set against a backdrop of Seneca Lake, featuring an inviting exterior with a substantial lawn. Well-maintained landscaping surrounds the driveway, which curves gently towards the entrance, complemented by trees that provide natural shade.

Chalet in Penn Yan

4.96 out of 5 average rating, 132 reviews

Finger Lakes Wine Country Chalet

The sunrise over Seneca Lake from this large A frame home are breathtaking. This newly remodeled, immaculate property features not only amazing views of Seneca Lake but two huge blue stone fire places, accommodations for up to 8 folks and all the comforts of a modern wine country vacation property. All new furnishings, floors, counter tops and finishes throughout. New leather furnishings in the living area. Enjoy outdoor living on the massive lake facing deck which has a sitting and dining area.

Guest favorite

A serene outdoor space features white Adirondack chairs and a small table, positioned on a deck overlooking Keuka Lake. The clear blue water reflects the sky, while lush green hills provide a picturesque backdrop. A covered dock is visible to the right.

Cottage in Dundee

4.97 out of 5 average rating, 38 reviews

Keuka Lakefront Cottage

Enjoy the best the Finger Lakes has to offer on the premier east side of Keuka Lake. This recently renovated home sits directly on the water and features a modern kitchen, full size bath, and two bedrooms complete with memory foam beds. All the comforts of home with central heat/AC and 3 stage water filtration system. Outdoor space includes a spacious dock, covered gazebo, smart TV, and hot tub. Enjoy the sunset with a glass of wine on the dock from the #1 winery in NYS located 1 minute away!

Guest favorite

Home in Burdett

4.92 out of 5 average rating, 38 reviews

Mi Casa tu Casa Lakeview Hot tub walk to wineries

Seneca wine trail lake view cottage. Location Location Location! Walk to Catherine Winery & The Elf on Oak restaurant. 4 miles from downtown Watkins Glen which offers boat launches, beach, kayak rentals, restaurants, state park. Well equipped kitchen. Hot Tub & fire pit. High speed wireless internet and work space room. Large private back yard with patio picnic set & gas grill. 1 King bed, 1 Queen room, 2 Twin room, 2 full bathrooms. Surrounded by wineries, breweries, distilleries, restaurants.

Top guest favorite

A spacious outdoor area is highlighted by a fire pit surrounded by four red Adirondack chairs. The well-maintained lawn extends towards the house, which features large windows reflecting the bright blue sky and scattered clouds.

Cabin in Hector

5 out of 5 average rating, 71 reviews

Sunset Paradise, Hector NY

Come and enjoy the stunning sunsets and vista views from your private patio to “get away from it all”. ALL NEW CONSTRUCTION created from the ground up with every detail in mind. Enjoy the spacious 1 bedroom home with queen and additional queen sofa bed in the living room to allow for a more comfortable fit. Minutes to top winery’s and wonderful restaurants! Included is a stocked coffee bar for early mornings and a fire-pit for sunsets and late evenings. Great for 4 adults or a family getaway!

Guest favorite

Home in Campbell

4.91 out of 5 average rating, 191 reviews

Close to Corning, Watkins Glen, Finger Lakes

All the comforts of home; Perfect for couples, families, solo, or business travelers. Superior accommodations close to I 86. Wi-Fi, internet, parking, full kitchen, TV – with ROKU, private setting. Vaulted ceilings, with large windows, river views, from large deck with 2-person hot tub just outside screen tent with gas fire pit and deck furniture. 10 minutes from Corning and ½ hour from Finger Lakes and Wine Country. We DO NOT accept local bookings without our prior approval. Please inquire.

Top guest favorite

A cozy fire pit adorned with glass stones flickers gently, surrounded by a well-maintained lawn. The backdrop features a sunset that paints the sky in soft hues, with a view of distant trees and water visible in the horizon.

Home in Burdett

4.97 out of 5 average rating, 410 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 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.

Guest favorite

A vibrant sunset casts orange and pink hues across the sky, reflecting on the tranquil pond. Lush greenery surrounds the water, and a deck with white railings overlooks the picturesque scene. The expansive landscape features rolling vineyards and glimpses of Seneca Lake in the distance.

Tiny home in Burdett

4.94 out of 5 average rating, 157 reviews

Vineyard Villa B

Make your memories here! Conveniently located on the Seneca Lake Wine Trail, enjoy beautiful panoramic views overlooking sprawling Vineyards and Seneca Lake. There is much for you to do (and taste!) here in the Finger Lakes, so grab your favorite person and treat yourself to an unforgettable stay! ✔ 2 Private Balconies with Views ✔ Located on the Wine Trail ✔ Living Room ✔ Full Kitchen ✔ Large Yard (Fire Pits, Grill, Seating) ✔ Smart TV ✔ Wi-Fi ✔ Parking ✔ Onsite Restaurant See more below

Superhost

A cozy living area features a leather sofa and a wooden coffee table atop a textured area rug. A stone fireplace serves as a focal point, while large glass doors provide natural light and a view of the surrounding nature. A guitar hangs on the wall, adding character.

Guest suite in Canandaigua

4.81 out of 5 average rating, 178 reviews

Tree House views, designer decor, child friendly

Our modern guest home is surrounded by nature and ideal for couples and families with children. You'll have a large deck, fireplace, fully equipped kitchenette, private bedroom (King bed), our guest favorite sleeping loft with a private balcony with views of Canandaigua Lake. Pack light, we provide supplies for children, remote work, & fitness. Community amenities include racket courts, playground, & beach. Jump in the lake, tour wine country, and hike bike or ski at Bristol Mountain.

Top guest favorite

A clear view of a grassy pathway leading toward the lake, flanked by two houses. The well-maintained lawn features small shrubs and flowers, while the distant water is visible beyond the tree line, inviting peaceful lakeside exploration.

Home in Canandaigua

4.95 out of 5 average rating, 21 reviews

Short-Term/Corporate/Utilities Included!

Lake access, fully furnished in a quiet, walkable, neighborhood. Utilities included! Close to wine country, breweries and cideries, Bristol Mountain skiing, downtown shopping, restaurants, and less than 30 min. to Roch. Enjoy CMAC which is walkable, or the NYS Wine Ctr. A great walking and biking area with easy access to the City Pier and great sunsets from the front porch or sunrises from the back deck! The host has tremendous knowledge of the FLX area and will answer any questions!

Guest favorite

A wooden dock extends into the calm waters, featuring a covered boat hoist with safety harnesses. A sitting area with a bench is positioned at the dock's edge. The horizon showcases a serene lake reflecting the sky, while gentle waves create a peaceful ambiance.

Home in Penn Yan

4.81 out of 5 average rating, 59 reviews

Cozy New England cottage west side Seneca lake

Cozy whole house, all season cottage, central to wine and beer trails. Enjoy this lakeside setting with your favorite wine. Fiber optics wi-fi. Beach firepit, gas fireplace for those winter days. 100' expanded dock with covered boat hoist. A/C . Covered grill area and covered deck area six miles to nearest boat launch and rentals. Separate firepits, shared dock, kayaks and paddle boat with Bungalow rental. Pets allowed as long as $50. PET fee is paid.

Superhost

The exterior showcases a charming house nestled among trees, featuring a combination of wood and stone elements. Lush greenery surrounds the property, while three neatly trimmed conical shrubs line the front. The entrance includes intimate outdoor lighting, enhancing the welcoming appearance.

Vacation home in Naples

5 out of 5 average rating, 5 reviews

Village Chalet - Walk to Breweries & Wineries

This 2 bedroom 1.5 bathroom boasts an open floor plan with bedrooms on opposite ends of the house for the ultimate privacy. One king bedroom opens up to the back ground level patio through its French doors. The other bedroom also has a king bed and includes an attached 1/2 bath and balcony with French doors. The main bathroom is large with bathtub & shower combo and includes Jack and Jill sinks for extra space. Enjoy the brand new pergola out back with lights and a fire pit.