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.

Crows nest lake view flat

Crows Nest is located on the Keuka Lake wine trail. It is next to Red Jacket Park and Morgan Marine on one side, Seasons on Keuka Lake on the other. Very close to Penn Yan/Yates County Airport and between the Main Deck restaurant and Route 54. The property is NOT water front. Keuka Lake is accessible thru Red Jacket Park and visible from the property, but not directly on the water. There is a sidewalk from the property to town for Guests who prefer to walk, approximately 1 mile to Village center

Farm House Suite 15 minutes from Bristol Mountain

Country location on a quiet road just minutes from Canandaigua Lake, and Bristol Mountain. Large farmhouse, with private suite including a huge great room (450 sf), wrap around screened-in porch. Please note that bedrooms and bath are upstairs. Geothermal heating/cooling. No full kitchen or downstairs sink available, only toaster oven, mini fridge, coffee maker (Keurig) with seating for 4 in section of great room. TV, fast Wifi for all your devices. Plenty of privacy and room to spread out.

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.

All Seasons Base Camp - Finger Lakes

*King sized bed; Private Entrance; Keurig Coffee Machine; Roku TV; Mini Fridge; Microwave; Toaster; Walk to Main Street, restaurants, wineries, distillery and breweries* All Seasons Base Camp is perfect for a couple or 2 friends looking for a comfortable and convenient place to stay while visiting the Finger Lakes Region for hiking, biking, fishing, skiing, water falls chasing, and wine tasting! No A/C needed.stays cool in the Summer months due to the home being built into the side of a hill.

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.

Offgrid Tiny home with private ponds, Finger lakes

This tiny house is surrounded by forest and ponds, just out of Naples. You will have private access to a pond and 15 acres of forest. In winter you are minutes away from Bristol mountain ski resort and Hunt hollow ski resort. For cross country skiing there is Cummings nature centre down the road. This property is in a prime area with lakes to kayak or fish on, many hiking trails including Grimes Glen, and the wine routes and arts and crafts the finger lakes are known for. 2 nights minimum

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

The Creek House Private Home & Scenic Grounds

The Creek House: a fully renovated 1 bdrm, 1 bath home with a full modern kitchen and large new deck situated right next to a year round babbling brook. The creek is 15 feet from the foot of the deck stairs; its sounds lull guests to sleep each night. Frogs, salamanders, crayfish, and all manner of forest life abound. The stream meanders through the mixed park like and wooded parcel ending at a 25’ wide 6’ high waterfall. Antique clawfoot tub. Water may have a sulfur smell (see below).

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, “Murphy “bed and furniture to relax or watch tv. The kitchen is small and equipped to prepare simple meals.

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!

Finger Lakes 1 Bedroom Private Suite

This private 1 bedroom (queen and twin daybed) in-law style suite in the Bristol Hills has keyless entry, deck, bedroom, living area, bath with both shower and jetted tub and breakfast bar. (The property is connected to the owners living area by locked door for your privacy and nestled on a back road in a rural area of the finger lakes. Views of the woods from all windows. If this room is booked, please check out our other listing on this property “Peaceful Finger Lakes”