Vacation rentals in Middlesex

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

Family · Value · Hospitality

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!

Family · Value · Laundry

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

Family · Location · Wifi

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!

Value · Location · Backyard

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.

Family · Value · Sleep quality

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!

Location · Family · Check-in

Maiden Lane Charm

Cozy updated cottage within walking distance and access to a private community beach. 2 bedrooms, fully equipped kitchen, bath and living space. This charming 800 sq foot home features a gas fire place to keep you cozy in the winter and an upper deck with lake view for relaxing in the warmer months. Large yard, partially fenced in, with play house for children. The storage shed houses outdoor games and wagon for the short trip (.3 miles) to the beach. 4 miles from CMAC.

Value · Location · Checkout

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.

Family · Location · Comfort

The Chosen Spot: lakefront, hot tub, wineries, ski

The home is the last house on a private road, in a cove with distant neighbors, offering great privacy & solitude. A family of bald eagles nests in the cove. The huge 2nd story deck adorns the entire front of the house. Best views on the lake to enjoy your morning coffee or afternoon glass of wine while soaking in this little slice of heaven. Bring your boat, we have a whip mooring & hoist. Boat launch 3 mi Note: late June -Labor day, 7 nite min checkin/out Fri only.

Value · Location · Walkability

The Canandaigua Farmhouse. Private, lake access

Kick back in this warm, relaxing, stylish, renovated circa 1900 Farmhouse. Keep warm by the camp-style firepit in a peaceful 2-acre setting. Watch the sunset from the back deck. A short walk to the neighborhood store, ice cream, pizza and Eastside Bar & Grill. A short walk through the backyard with access to beautiful Canandaigua Lake. Close to wine tasting in the Finger Lakes, Naples, Bristol and Hunt Hollow Ski hills, wedding venues, and summer concerts at CMAC.

Location · Family · Nearby

Beautiful Keuka Lake home close to Penn Yan.

Welcome to Keuka lake in this beautiful home that boasts 3 master suites. The living room has a panoramic view of Keuka Lake. There is a deck off the top floor and a patio off the first floor to sit and enjoy the lake view as well. From the downstairs patio you are only a few steps to the beach. At the end of the dock the lake is only 3 feet deep so it’s excellent for swimming. Everything in this house is new and very clean. We are a mile from downtown Penn Yan.

Value · Family · Quiet

Sanctum at Sunset Lake

Sanctum at Sunset Lake is a private, design-forward retreat on the coveted east shore, offering rare, unobstructed sunset views across the water. Thoughtfully curated with natural textures and expansive windows, the home blurs indoor and outdoor living. Mornings bring soft light and stillness; evenings are reserved for golden hour and quiet reflection. Designed for rest, presence, and elevated comfort, Sanctum is more than a stay—it’s a reset.

Location · Family · Hot tub