Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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Top guest favorite
Tiny home in Burdett
4.99 out of 5 average rating, 119 reviews

FLX 2-Lake View Tiny Cabin

Nestled up on a hill overlooking Seneca Lake, watch the sunset while laying in bed or from your own patio with a fire crackling. We are local hosts and will make sure you have an unforgettable stay! Everything you could want to do in the Finger Lakes will be at your fingertips. Wineries galore, two even just next door, multiple breweries nearby, minutes to the lake, 15 minutes to downtown Watkins Glen, 10 minutes to hiking trails at the national forest, or stay in, relax, and enjoy the view!!

Top guest favorite
A hot tub is situated on a wooden deck, offering a view of Canandaigua Lake and the surrounding snowy landscape. The tranquil scene is enhanced by the soft hues of a sunset sky, with trees framing the view in the background.
Chalet in Naples
4.97 out of 5 average rating, 138 reviews

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

Top guest favorite
A comfortable living area features a green sofa paired with a wooden rocking chair. A dark coffee table sits in front, with natural light illuminating the space through two windows. A dining table with four chairs is positioned nearby, creating a cozy gathering spot.
Apartment in Penn Yan
4.97 out of 5 average rating, 551 reviews

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

Top guest favorite
The exterior of a large farmhouse is depicted, with a well-maintained lawn featuring a mature tree and colorful autumn foliage. A pathway leads to the entrance, and large windows provide ample natural light inside. Clear blue skies enhance the tranquil setting.
Guest suite in Bloomfield
4.94 out of 5 average rating, 423 reviews

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.

Guest favorite
Home in Canandaigua
4.92 out of 5 average rating, 274 reviews

Bristol Retreat 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.

Top guest favorite
A shaded outdoor area features a swing chair with soft cushions, providing a comfortable spot to relax. Lush green foliage surrounds the space, while colorful flowers add a vibrant touch to the scene, enhancing the natural surroundings.
Guest suite in Naples
4.94 out of 5 average rating, 361 reviews

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.

Top guest favorite
Cabin in Branchport
4.98 out of 5 average rating, 126 reviews

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.

Top guest favorite
The kitchen features modern appliances, including a stainless steel fridge and oven, set against light-colored cabinetry and a mosaic backsplash. A spacious island with bar seating offers additional workspace. Natural light filters through large windows, illuminating the open layout.
Farm stay in Penn Yan
4.98 out of 5 average rating, 245 reviews

Modern, bright & calm 1 BR / 1 bath farm retreat

Let the calm, quiet beauty of New York’s Finger Lakes region renew you at this modern and bright on-farm escape right on the Seneca Lake Wine Trail. Enjoy our outdoor space and the comfort of our new building's private second floor which features natural lighting, a private entrance, self check-in, marble countertops, tile throughout, a custom bathroom, in-floor radiant heat, WiFi, no TV and a spacious deck overlooking Black Squirrel Farms, a black walnut growing and processing operation.

Top guest favorite
A charming tiny house is set beside a tranquil pond, surrounded by vibrant autumn foliage. The reflections of colorful trees are visible in the calm water, enhancing the serene landscape. The gentle contours of the hillside form a picturesque backdrop.
Tiny home in Naples
4.95 out of 5 average rating, 106 reviews

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

Top guest favorite
The image captures a stunning lakeside view framed by large floor-to-ceiling windows. Soft pink and orange hues from the sunset reflect on the tranquil water, creating a serene ambiance. Outdoor seating is visible on the deck, allowing for enjoyment of the picturesque scenery.
Home in Rushville
4.96 out of 5 average rating, 187 reviews

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!

Top guest favorite
Two mugs sit on a balcony railing, overlooking a serene lake at sunset. The sky displays vibrant shades of pink and purple, reflecting on the water's surface, while distant hills create a peaceful backdrop.
Condo in Canandaigua
5 out of 5 average rating, 190 reviews

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

Top guest favorite
The exterior of the apartment is displayed, featuring a well-maintained garden bed with vibrant flowers. The entrance is marked by a white facade, adorned with floral arrangements under the windows. A brick pathway leads to the entrance, flanked by neat hedges.
Apartment in Naples
4.99 out of 5 average rating, 167 reviews

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.

Popular amenities for Middlesex vacation rentals

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