
Holiday rentals in Middlesex
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Top-rated holiday rentals in Middlesex
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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

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.

Secluded Cabin, Hot Tub, Fire Pit, Pets, Grill
Escape to the Black Birch Cabin – a stylish, romantic hideaway designed for couples. Tucked away in the heart of the woods, this cozy cabin offers ultimate seclusion w/ a private hot tub, a crackling fire pit, and serene forest surroundings. Perfect for unwinding together, whether stargazing by the fire, playing board games, enjoying the peaceful ambiance, or simply reconnecting. The Black Birch cabin invites you to relax, recharge, and create unforgettable memories in a truly magical setting.

Grandpa-T’s Guest Cottage at Hawks Landing
Welcome to Grandpa-T’s Guest Cottage at Hawks Landing… 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 cottage!

Lake House-Sunset Views-HOT TUB-Couples Retreat
Escape to the private and secluded Sunset Sanctuary where you can relax and enjoy 180 degree breathtaking views of Canandaigua Lake during the day and stunning sunsets from the wrap-around deck in the evenings. Enjoy amenities such as a hot tub, a cinematic experience, a grill and a fire pit. You are minutes from all Canandaigua has to offer-from CMAC, Canandaigua Boatworks, Deep Run Beach, and all the locally owned restaurants, shops and tasting rooms that make the Finger Lakes so iconic!

FLX lakeview w/ *NEW HOT TUB*, spacious 3 bd 2bath
Located in the heart of the Finger Lakes Wine Region there is no shortage of adventures to be had. Summer vacations with all the amenities of home and the fun of your own pond, a hot tub, fire pit and a large yard. Fall brings beautiful foliage, nearby wineries for tours, tastings & hiking trails. In the Winter, a 10 minute trip to Bristol Mountain for slope recreation or even sledding on our very own property. Close to CMAC concert venue and Naples Grape Fest for the best grape pie ever!

Charming Country Cabin- HOT TUB, Sunsets, CMAC
Let the stress melt away as you take a break and unwind at this peaceful oasis. The Cabin is a divine intertwine of a rustic cabin with an elegant master bedroom in a relaxed country setting. Enjoy a soak in the hot tub before you cozy up in front of the pellet stove! All in a fabulous location close to Canandaigua Lake, wineries, breweries, hiking and Naples. Beautiful downtown Canandaigua is a 12 minute drive away for shopping or dinner. Boat/horse trailer parking available. 7min to CMAC

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.

Finger Lakes Hilltop Chalet Relax, Unwind & Renew
This log cabin chalet tucked back in the woods invites you to kick back and relax, with a cozy fireplace, hot tub, and rejuvenating sauna adding to the luxurious atmosphere. Nestled in the woods on 9 acres, the property provides a tranquil haven, complete with walking trails that allow you to connect with nature. Whether you're enjoying the warmth of the fireplace or strolling through the peaceful surroundings, this home offers the perfect blend of comfort and tranquility.

The Johnson Chalet in Bristol/Canandaigua*HOT TUB*
Minutes from Bristol Ski Mountain, beautiful Canandaigua Lake, Finger Lake wineries, local breweries, restaurants and hiking trails or stay and relax at the Chalet! You can enjoy the hum of the relaxing jacuzzi spa, gaze at the scenery while sitting on the porch sipping your coffee, start a bon fire outside in the fire pit, or stay cozy indoors by the fireplace! Whatever you choose, this is your time to sit back, relax and be stress free at the Johnson Chalet!

Modern Farmhouse Whole Home Cozy Hot Tub
Escape every day life and relax in our modern farmhouse in the country! 2 bedroom, 2 bath includes high end amenities. Sleeps 4, Open floorplan w/ fireplace. Luxury spa like bathrooms. Bedrooms w/ high ceilings. Office w/desk Fast Wi-Fi. Washer/Dryer. Outdoor hot tub. Country feels Close to wineries, breweries, Bristol Mountain, Canandaigua Lake. Due to some amenities we ask for children to be 10+, 1 small dog under 30lb allowed, no cats.

Hi-Tor Hideaway. The Cure for Cabin Fever.
A beautiful log cabin in the woods with an incredible view, that sleeps 5. There is a queen bed downstairs, a double in loft and then a roll-away twin in living room. Peace and quiet, discovering nature and resetting yourself. Life has been a challenge and it is good to step back sometimes. Our peaceful retreat is centrally located near many parks and waterfalls. Located between beautiful Canandaigua, Keuka and Seneca Lakes.
Popular amenities for Middlesex holiday rentals
Other great holiday rentals in Middlesex

Spacious & Serene with Breathtaking Views

Little Red Cabin in the Woods

Keuka lake on the water

The Vandenbergh Mansion

Glen Hollow Guest House: Hot Tub/Sauna+Waterfall!

Cozy Cub Cabin

Canandaigua Lake Cottage!

Cloud Wine Canandaigua-Lake Views & Hot Tub in FLX
Destinations to explore
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- Letchworth State Park
- Cornell University
- Watkins Glen State Park
- Finger Lakes
- Bristol Mountain
- The Strong National Museum of Play
- Taughannock Falls State Park
- Sea Breeze Amusement Park
- Watkins Glen International
- Chimney Bluffs State Park
- Keuka Lake State Park
- Stony Brook State Park
- Keuka Spring Vineyards
- Robert H Treman State park
- Fox Run Vineyards
- Three Brothers Wineries and Estates
- University of Rochester
- Memorial Art Gallery
- Cascadilla Gorge Trail
- Buttermilk Falls State Park
- Genesee Country Village and Museum
- Montezuma National Wildlife Refuge
- Ontario Beach Park
- High Falls





