Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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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, 534 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

Guest favorite

The exterior of the cottage features a well-maintained stone pathway leading to the entrance. Lush greenery surrounds the home, with flowering plants and a wooden privacy screen partially visible. A patio area is seen, complete with outdoor seating and a grill, set against a backdrop of trees.

Cottage in Canandaigua

4.93 out of 5 average rating, 255 reviews

Creekside Bristol Cottage with Hot Tub & Fireplace

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, 347 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.

Guest favorite

A red log cabin is seen across a tranquil pond, surrounded by vibrant fall foliage. The reflection of the cabin and colorful trees creates a serene scene. The sky is clear and blue, enhancing the peaceful atmosphere of the property.

Cabin in Branchport

4.92 out of 5 average rating, 159 reviews

Retreat @ Keuka Cabin

It's The Cabin! This picturesque cabin sits on 8 acres of mowed and wooded land. Enjoy all that the property has to offer with a half mile's worth of walking paths, a large front porch to drink your morning cup of joe, fully stocked pond, a fire pit/wood and more. It offers serenity in the Finger Lakes Region. Easy access to countless wineries, breweries and distilleries. The cabin is where memories are forged, belly laughs are had, and adventures await. Come, kick back, and take it easy.

Top guest favorite

A hot tub is positioned under a covered deck, featuring clear water reflecting the blue sky. Lush green hills and trees are visible in the background, creating a serene natural setting.

Home in Naples

4.99 out of 5 average rating, 146 reviews

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!

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, 182 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

A cozy living area showcases a red leather sofa complemented by a white throw blanket. A patterned area rug covers the floor. A small dining table is positioned in the background, along with wooden chairs. Natural light enters through a door leading to the outside.

Guest suite in Bloomfield

4.96 out of 5 average rating, 117 reviews

Peaceful Finger Lakes Studio

Overlooking a 3/4-acre pond, this 550 sq ft lower-level studio has a private patio, 2 entrances, full bath, queen bed and newly installed kitchen (after 3/15/24). TV has access to Netflix, Disney plus, Prime Video, and other Roku channels (no cable). Wi-Fi is continuous with listing and space has private access to heat/AC controls. Entrance is via keypad lock. Close to Canandaigua, Cummings Nature Center, CMAC, and wineries/microbreweries. Short drive to Letchworth State Park and Victor

Guest favorite

The view from the front of the bus showcases a green landscape with rolling hills and scattered bales of hay. Potted plants rest neatly on the dashboard, adding a touch of life to the rustic interior. Sunlight filters through the windshield, illuminating the inviting scene.

Camper/RV in Naples

4.87 out of 5 average rating, 115 reviews

Off Grid Bus at Bright Sky Farm

Unplug- and recharge- in our rustic converted school bus. Swim in the pond, meditate in the garden, pick raspberries and see some of the best night sky viewing around. Visit with the farm animals and tag along for chores if you want. This skoolie is far from the swanky, expensive ones you've seen on social media- this is a simple, rustic and very old bus that we were lucky enough to live in with our kids while we looked for our perfect farm, and now we're happy to share it with you!

Top guest favorite

A hot tub is situated under a wooden pergola surrounded by vibrant fall foliage, with views of Canandaigua Lake in the background. Two Adirondack chairs offer a cozy spot to enjoy the scenery, while the structure features large windows capturing natural light.

Home in Naples

4.99 out of 5 average rating, 143 reviews

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!

Top guest favorite

A panoramic view of rolling hills is captured during sunset, with vibrant orange and pink hues highlighted by clouds. Lush greenery surrounds the scene, creating a serene natural landscape that invites relaxation.

Guest suite in Naples

4.97 out of 5 average rating, 386 reviews

Naples Escape: Artistic & Serene w/ Magical Views

Escape to a peaceful, artistic haven surrounded by nature’s beauty! This 10-acre gem offers sweeping views, a tranquil pond, and leisurely strolls. Just 2 miles from the heart of Naples, explore waterfalls, wineries, charming shops, and local dining. Perfectly situated for seasonal adventures, with Bristol Mountain and Cummings Nature Center both under 20 minutes away. Whether unwinding or exploring, this cozy sanctuary offers a harmonious balance of comfort and creativity.

Top guest favorite

The cabin exterior features a metal roof and a spacious deck with railing, surrounded by trees. A grill is positioned on the deck, and outdoor seating is available. The serene landscape showcases a glimpse of Canandaigua Lake in the background.

Guesthouse in Naples

4.97 out of 5 average rating, 274 reviews

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!

Top guest favorite

A modern kitchen is presented with a spacious island topped with sleek granite and featuring white cabinetry. Pendant lights hang above, illuminating the area. A dining table with four orange chairs is visible in the background, complemented by a large window that allows natural light.

Chalet in Canandaigua

4.97 out of 5 average rating, 285 reviews

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!