
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.

CMAC - 420 Friendly Horses Private Quiet Romantic
Our visitors have only 5 star reviews for Finger Lakes High View. " Best stay ever!"; "Clean, quiet and peaceful". Our working horse farm offers a comfortable stay; spectacular fall vistas and is only 6 miles from Canandaigua Lake. Chill with a beverage in our 3 season room. Visit with our horses. They are guest friendly and love carrots (provided). You will have a 5 star experience in this immaculate historic home-away-from-home that offers proximity to Canandaigua and a 420 friendly stay.

The Lakeview Chalet: Cozy & Chic, Hot Tub, Games
Relax & unwind to a backdrop of Canandaigua Lake! This rustic chalet on a private setting has that cozy cabin feel with modern styling and luxurious amenities including a gas stove fireplace, hot tub, nostalgic games, library, outdoor fire pit & more! Amenities Include: Hot Tub with Lake View Gas Stove/Fireplace Fire Pit BBQ Grill Foosball Table Board Games A/C in Loft BR Heat Parking: 4 Spaces High-Speed Internet/Wifi Smart TV/Cable Library Desk Alexa Speaker Telescope STR Permit #: 2023-0073

Bristol Creekside Cottage
Unwind at this romantic getaway nestled in the beautiful Bristol Hills, just minutes away from Bristol Ski Resort, Canandaigua and Honeoye Lakes. This unique 1 bedroom 1 bathroom cottage is one of our two homes on the property along the peacefully flowing Mill Creek. Take in the natural beauty from the large patio and hot tub. Inside, enjoy the warmth of the gas fireplace, complimentary wifi and smartTV. The full kitchen and bathroom are well stocked with amenities to ensure a comfortable stay.

22 Acre Private Finger Lakes Wine Trail Getaway
This 2023 professionally remodeled farmhouse cabin has everything to make your stay luxurious and comfortable. Located at the highest point in Yates County, up on Italy Hill, and in the heart of New York's Finger Lakes, this cabin is nestled among 22 private acres of serene forest, bordering state land & the Finger Lakes Hiking Trail. Enjoy your private 1-acre spring-fed pond, stocked with smallmouth, carp, perch, and bluegill. Enjoy the outdoor 7-person hot tub and fire pit to finish your day.

Keuka Beach House - Glamping at its best!
My place is right on the lake and great for summer activities. The deck hangs out over the water overlooking the beach and dock. Outdoor opportunities include your own hiking trail on five acres of land behind the house, cycling, swimming, kayaking and canoeing. It's a great place for couples, solo adventurers, and pets who like to swim. Currently, New York State charges 8% sales tax and Yates County charges 4% Occupancy Tax which is added to the amount you pay when booking the space. Sorry.

Lakefront Retreat
Enjoy Gorgeous Panoramic Views of the Lake & surrounding Hillsides from the private & spacious balcony. PERMIT #2023-0075 Immaculate & Modern - 1 Bedroom 1 Bath condo, fully equipped Kitchen, Cozy Living Area, 70" TV with Netflix & Internet TV/Music Channels, use your streaming services etc. Leather Recliner, mesmerizing LED Fireplace , Very Comfortable King Bed, Washer, Dryer, Stylish Spa Bathroom and a Furnished Balcony w/ electric grill & a Finger Lakes View to Capture your Heart

Suite Dreams
The entrance to the apartment has mats for shoes or boots and hooks for coats and backpacks. The bedroom has a queen size bed and full bath with a tub and shower attached. There has been a smart tv added to the bedroom wall since the pictures were taken. On the garment rack there are extra pillows, linens and a fleece blanket for your convenience. The living room has a half bath, air mattress and furniture to relax or watch tv. The kitchen is small and equipped to prepare simple meals.

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!

Hook, Wine and Sinker
Completely updated in 2022! Canandaigua lakefront 5 minutes outside of Naples, NY! Level lakefront- Stunning views of South Hill- perfect for autumn leaf gazing and also summertime swims off the permanent dock. With kayak, inflatable toys, gas BBQ, WiFi, cable TV & electric awning over a picnic table. Enjoy s’mores over the campfire pit. Tastefully decorated, well equipped kitchen, washer/dryer & bedroom AC. Escape to the vineyards, Bristol Mtn. & all the Finger Lakes has to offer!

Secluded, Hot Tub, Fire Pit, Deck, Grill, Pets
Discover Creekside Hideaway – the perfect romantic getaway. Nestled by a tranquil creek, this cozy retreat features a private hot tub, a crackling fire pit, and a gas fireplace for ultimate relaxation. Surrounded by nature, it’s ideal for unwinding together, exploring nearby trails, or simply savoring peaceful moments. Whether reconnecting over a fire or soaking under the stars, Creekside Hideaway offers a serene escape to create lasting memories in a secluded, scenic setting.

The Lakeview House in South Bristol
Just 5 miles from Bristol Mountain! Nestled in the Bristol Hills with stunning views of Canandaigua Lake. Near many hiking trails on state lands, or explore the acres of woods in our back yard. Enjoy the wineries, breweries, and all the other unique experiences offered in the Finger Lakes region. Then come home, build a campfire and enjoy incredible views from the lean-to, relax in the hot tub, or sit by the fireplace and watch a movie! You'll love your Lakeview vacation!

Hawks Landing - Your Romantic Getaway! New Pricing
Welcome to Hawks Landing Cabin… your romantic getaway! Located in the heart of the Finger Lakes, this extraordinary property perched above Canandaigua Lake with its spectacular views is within minutes of all the region has to offer. Hiking, fishing, boating, cycling, kayaking, snow many opportunities our guests can enjoy locally or just simply unplug and relax in the quiet of this cozy cabin. Come celebrate your special moments in the privacy of this beautiful cabin!
Popular amenities for Middlesex vacation rentals
Other great vacation rentals in Middlesex

Lake View with Balcony- Private 2 bedroom chalet

Lakeview house six min to Bristol Mt in S. Bristol

Luxury Cabin | 55 Acres, Ponds, Hot Tub & Game Rm

Luxury Lakeview Retreat Hot Tub, Gym & Theatre

New property on historic farm with lake views

Getaway in the Heart of Wine Country!

Canandaigua Lakefront | 5 Mins to Naples | Dock

Bobcat Bungalow
Destinations to explore
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- Cornell University
- Letchworth State Park
- Watkins Glen State Park
- The Strong National Museum of Play
- Bristol Mountain
- Sea Breeze Amusement Park
- Chimney Bluffs State Park
- Taughannock Falls State Park
- Watkins Glen International
- Keuka Lake State Park
- Stony Brook State Park
- Keuka Spring Vineyards
- Cascadilla Gorge Trail
- Finger Lakes
- High Falls
- Three Brothers Wineries and Estates
- Fox Run Vineyards
- Sciencenter
- Memorial Art Gallery
- Ontario Beach Park
- Cayuga Lake State Park
- Buttermilk Falls State Park
- Montezuma National Wildlife Refuge
- Ithaca College





