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Middlesex Vacation Rentals

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    Don't let other travelers get your favorite Middlesex area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Middlesex
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    Historic Post Office Cottage with shared Lake Access1 / 40
    (1)Average
    Middlesex
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    The Lighthouse1 / 17
    (1)Excellent
    Middlesex
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Middlesex
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Middlesex
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unwind with that special someone at this 2-bedroom, 2-bath Naples vacation rental house on 6 private acres. Set between Keuka and Canandaigua lakes, this year-round getaway boasts spectacular views of Italy Valley. Accommodations for 6 guests, cathedral ceilings, natural wood interiors and an...
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    Location Information
    Middlesex, Finger Lakes 14512
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 10 miles of Middlesex.
    Branchport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • Cable/satellite TV
    • Central Heating
    • DVD Player
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Evergreen Vista is a year-round exquisite private retreat nestled in the heart of the Finger Lakes wine country - a wooded beauty that changes with every season! Fish, canoe and hike on this lush and expansive estate; shoe-shoeing and x-country skiing in winter. The spacious, modern and unique...
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    Branchport, Finger Lakes 14418
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Naples
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Washer
    • Central Heating
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Full of art, treasures and photos from around the world, our unique, cozy home welcomes you! Relax in the library, sink deep in our leather couches, build a bonfire, drink wine overlooking the creek, sip tea on our covered porch, hike the local trails, walk to wineries & waterfalls-Naples has it...
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    Location Information
    Naples, Finger Lakes 14512
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    Lake Canandaigua Homestead & Studio1 / 12
    (2)Very good
    Naples
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Yard
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Outdoor Dining Area
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 11, 2016
    A nice little apartment for two. It had everything we needed with plenty of room. Close to Naples or Canandaigua so there was plenty to see and do. Would definitely consider...
    Reviewed September 11, 2015
    Very nice place, studio equipped with everything needed. Close to all Finger Lakes attractions. We were staying there 7 days enjoying Corning, Geneva, Watkins Glen and other...
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    About this property
    REDUCED PRICE for winter! 5 MILES FROM BRISTOL MOUNTAIN! WINE COUNTRY'S Favorite region on LAKE CANANDAIGUA! Family vacations, weekend get-a-ways, a few miles away from boating, kayaking, golfing, skiing, wine tasting, shopping, dining, biking, and more. Center yourself around the beauty of the...
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    Naples, Finger Lakes 14512
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Branchport
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Patio
    • Balcony
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax and vacation in style at 'Maison Du Lac', which means 'Lake House' in French! This lakeside property feels fresh and inviting as you enter through the front door. The three levels of living space, a large deck with a new permanent dock, and a nice gradual lakefront, makes this the...
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    Branchport, Finger Lakes 14874
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Near Wineries, Trails, And Skiing! Woodland Cabin1 / 10
    (1)Excellent
    Naples
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Grill
    • Cable/satellite TV
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 21, 2016
    We were pleasantly surprised with the sweet, cozy cabin in the woods. Very comfortable and well equipped. Traveling with my husband, daughter and her new husband - so 4...
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    About this property
    Get away from it all but stay close to civilization and fun at our rustic cabin located a short drive from hiking, cross country skiing, and snowshoeing trails, several Finger Lakes wineries, hunting, fishing, and just a 23 minute drive to Bristol Mountain Ski Resort. Our year-round cabin is...
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    Location Information
    Naples, Finger Lakes 14512
    Cabin - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Lake Canadaigua Homestead & Apartment1 / 11
    (3)Average
    Naples
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • Air Conditioning
    • Patio
    • Grill
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2015
    The apartment is offered at rents much lower than what you typically will get in the area. It is a pretty good bargain. This is similar to an AirBnB kind of arrangement, you...
    Reviewed May 28, 2015
    My wife and I stayed at this apartment over the Memorial day weekend, and we had a nice time there. Branden and Crystal were excellent, as well as their children. The apartment...
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    About this property
    REDUCED PRICE for winter! 5 MILES FROM BRISTOL MOUNTAIN! WINE COUNTRY'S Favorite region on LAKE CANANDAIGUA! Family vacations, weekend get-a-ways, a few miles away from boating, kayaking, golfing, skiing, wine tasting, shopping, dining, biking, and more. Center yourself around the beauty of the...
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    Location Information
    Naples, Finger Lakes 14512
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Rushville
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re looking for an affordable, peaceful getaway with country cottage charm, you’ll appreciate Precious Moments! This adorable 3 bedroom bungalow is located just a short 1/4 mile walk from the scenic, tree-shrouded swimming beach, where children will enjoy playing in the water and guests can...
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    Rushville, Finger Lakes 14424
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Bluff Point
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Parking
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just five miles from downtown Penn Yan, this property is tucked away in a beautiful neighborhood on East Lake Road. Privacy is afforded by the ample space between neighboring homes. The cottage sits on the water's edge and has a gorgeous view of Keuka Lake. It has been renovated with...
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    Location Information
    Bluff Point, Finger Lakes 14527
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Naples
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Main House Suite sleeps four people and has a fully equipped kitchen. This unit is attached to the owners main house but is completely private. It is handicap-accessible with a private elevator entrance from the garage. This rental also includes: en suite work space and desk, beautiful view of...
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    Location Information
    Naples, Finger Lakes 14512
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Bristol
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Parking
    • Wi-Fi
    • Patio
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect home for a Finger Lakes visit at any time of the year. Deer View is a fully furnished, three bedroom townhome located just minutes from Bristol Mountain which is absolutely ideal for winter sports enthusiasts such as skiers and snowboarders. Whether you're looking for a romantic getaway...
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    Location Information
    South Bristol, Finger Lakes 14424
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Naples
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Yard
    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    North House is a private, two-bedroom rental that sleeps six to seven people. It has a spacious living room with a sofa bed and a full kitchen with breakfast bar. This rental also includes: Dining room table with seating for six, one full bathroom with a shower and an extra large bathtub, half bath...
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    Location Information
    Naples, Finger Lakes 14512
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Naples
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Yard
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our North Bunk House if off-grid and solar powered. It’s a three-bedroom home that sleeps five-six people. There’s a cozy first floor living room with a great view of Mr. Waddles Pond and our duck house. This rental also features a full kitchen with breakfast bar, tastefully finished full bathrooms...
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    Location Information
    Naples, Finger Lakes 14512
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Bluff Point
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Parking
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With great space for relaxing lake living, both inside and out, and a location near many local hotspots of adventure, Edgewater Escape is ready to accommodate for the tastes and needs of any and all beach-goers! Descend the stairs from the road to this bright and airy classic beachside home...
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    Bluff Point, Finger Lakes 14527
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Naples
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gather your friends and family for a getaway at ‘The Grape Escape,’ a 5-bed, 2-bath vacation home in the Finger Lakes, New York's Wine Country, resting on over 6 private acres in Naples. Constructed in 1906, this 2,500-square-foot home was recently updated to provide 12 guests with modern...
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    Location Information
    Naples, Finger Lakes 14512
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Naples
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're planning on taking a vacation to the Finger Lakes Region, don't settle for anything less than accommodations with views of one of the lakes. Stay at this majestic 4-bedroom, 2-bathroom vacation rental cabin in Naples overlooking Canandaigua Lake. Spend your days kayaking and boating on...
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    Location Information
    Naples, Finger Lakes 14512
    Cabin - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Middlesex Flight and Weather Info
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    42° 28°
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    33° 20°
    December
    26° 13°
    January

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