Vacation rentals in Middlesex

Timber View At Timber Trails

Escape to the countryside at the charming, “Timber View.” Surrounded by wineries & scenic beauty, this country retreat offers a peaceful getaway for those seeking to disconnect & rejuvenate. Wake up to the sounds of nature, enjoy your morning coffee on the porch, & spend your days exploring the Finger Lakes region with activities like hiking, visiting local farmers' markets, or simply enjoying the tranquility of rural life. In the evenings, gather around the fire pit for stories and stargazing.

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.

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.

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.

Hideaway House >HOT TUB< *Secluded w/Amazing Views

The Getaway Hideaway House is tucked near the scenic Honeoye and Canandaigua Lake Wine & Brewery Trail—perfect for wine lovers, adventurers, and those seeking a peaceful escape. Enjoy stunning valley and hillside views from the living room or while relaxing in the year-round covered hot tub on the patio. Just a short drive (under 10 minutes) to Naples for great dining and entertainment. Note: Due to the hillside location, AWD or 4WD is recommended during inclement weather for safe access.

Guyanoga Getaway ~Peaceful~ 5 min. to Keuka Lake

Nature lovers! Ideal vacation home for a small family, couples getaway or girls/guys weekend. Nestled in the woods, this secluded cabin-like ranch home has a beautiful view of the Guyanoga Valley. Located only 2 miles from Keuka Lake State Park, and a short drive to Penn Yan, this 3-bedroom has all of the comforts of home. Enjoy a cup of coffee on the deck. Minutes away from the lake; breathtaking scenery, wineries and craft breweries. You'll find small-town hospitality in Yates County.

Honeoye Hidden Gem!

Stay in our cozy, completely renovated cabin in the woods where elegance meets quaint…nestled in the Finger lakes and wine country region..to include craft breweries as well..Includes all new appliances /heat /AC with all the comforts of home! Also has an automatic generator in the rare event of power failure. This property offers 1 mile of mowed trails and 60 acres to explore! Hiking, cross country skiing and snowshoeing available.Snowmobiling trails and ski resorts just minutes away.

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

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!

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!