Title: Visit Middlesex: 2026 Travel Guide for Middlesex, New York | Expedia.com [Hotels in Middlesex](https://expedia.com/Middlesex-Hotels.d553248635935228195.Travel-Guide-Hotels)[Vacation Rentals in Middlesex](https://expedia.com/Middlesex-Vacation-Rentals.d553248635935228195.Travel-Guide-VacationRentals)[Flights to Middlesex](https://expedia.com/Cheap-Flights-To-Middlesex.d553248635935228195.Travel-Guide-Flights)[Car Rentals in Middlesex](https://expedia.com/Car-Rentals-In-Middlesex.d553248635935228195.Car-Rental-Guide)[Middlesex Vacation Packages](https://expedia.com/Middlesex.d553248635935228195.Destination-Travel-Guides) # Middlesex, NY ## Travel Guide ![Cascade at Clark's Gully #Localsecrets #Mybackyard](https://images.trvl-media.com/place/553248635935228195/ac70f7cc-08c7-42a3-92ce-851b61158d87.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Cascade at Clark's Gully #Localsecrets #Mybackyard](https://images.trvl-media.com/place/553248635935228195/ac70f7cc-08c7-42a3-92ce-851b61158d87.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Middlesex Things to do ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_SPRING_PROMO_553248635935228195) - Middlesex Hotel Deals - Vacation Rentals in Middlesex ![The Lake House on Canandaigua](https://images.trvl-media.com/lodging/50000000/49090000/49087800/49087717/07c0c541_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Lake House on Canandaigua 770 South Main Street Canandaigua NY Fully refundableReserve now, pay when you stay $273 nightly $310 total Feb 26 - Feb 27 Total with taxes and fees Book a stay at this luxury hotel in Canandaigua. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ... 9.2/10 Wonderful! (449 reviews) Everything was amazing! Reviewed on Feb 2, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F26%2F2026&endDate=2%2F27%2F2026&selected=49087717&PinnedHotelID=49087717&HadPinnedHotel=true®ionId=553248635935228195) ![41 Lakefront Hotel, Trademark Collection By Wyndham](https://images.trvl-media.com/lodging/1000000/70000/60800/60711/c46b1bc3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 41 Lakefront Hotel, Trademark Collection By Wyndham 41 Lake Front Blvd Geneva NY $86 nightly $98 total Feb 15 - Feb 16 Total with taxes and fees Book a stay at this business-friendly hotel in Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms ... 8.2/10 Very Good! (1,076 reviews) Clean room and great mattress! Reviewed on Feb 9, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=60711&PinnedHotelID=60711&HadPinnedHotel=true®ionId=553248635935228195) ![Hotel Canandaigua, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/51000000/50900000/50896900/50896866/8aa2072d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Canandaigua, Tapestry Collection by Hilton 205 Lakeshore Drive Canandaigua NY $139 nightly $157 total Mar 16 - Mar 17 Total with taxes and fees Stay at this hotel in Canandaigua. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions ... 8.8/10 Excellent! (320 reviews) Size of room, gym was great Reviewed on Feb 10, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=50896866&PinnedHotelID=50896866&HadPinnedHotel=true®ionId=553248635935228195) [See all 1,425 properties in Middlesex](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F14%2F2026&endDate=2%2F15%2F2026®ionId=553248635935228195) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK](https://images.trvl-media.com/lodging/19000000/18770000/18761700/18761695/1a8885fe_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK Dresden NY Stay at this vacation home in Dresden. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Keuka Lake Outlet Trail and Prejean Winery ... 9/10 Wonderful! (282 reviews) Cozy cottage with everything you need. Amazing view of the lake and sunrise and nature. Cottage was clean and thoughtfully stocked with games, books, cookware, extra blankets and pillows. Best thing was the hot tub. Sitting in there at night with a ten degree temp and a light snow was relaxing and ... Reviewed on Feb 1, 2026 [](https://expedia.com/Dresden-Hotels-Lake-Dreamin-Seneca-Lake-Waterfront-Hot-Tub-Wine-Trail.h18761695.Hotel-Information) ![Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..](https://images.trvl-media.com/lodging/19000000/18980000/18979100/18979043/41fb588c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region.. Naples NY Stay at this cottage in Naples. Enjoy free WiFi, a water park, and patios. Popular attractions Naples Community Park Disc Golf Course and Clarks Gully are located ... 8.6/10 Excellent! (239 reviews) The cabin was just what we were looking for- a quiet escape. Hot tub and video games made it that much better. Thank you! Reviewed on Jan 19, 2026 [](https://expedia.com/Naples-Hotels-Nature-Lovers-Getaway-Nestled-In-The-Hills-Of-The-Finger-Lakes-Region.h18979043.Hotel-Information) ![Serenity Place: lake home with hot tub, pool table/game room, and private lakefront](https://images.trvl-media.com/lodging/35000000/34330000/34321400/34321327/dabe71fa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Serenity Place: lake home with hot tub, pool table/game room, and private lakefront Penn Yan NY Book a stay at this family-friendly vacation home in Penn Yan. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Prejean Winery and ... 9.8/10 Exceptional! (83 reviews) Great views. Cozy house. Perfect for a family get away. Reviewed on Dec 1, 2025 [](https://expedia.com/Penn-Yan-Hotels-Serenity-Place-Lake-Home.h34321327.Hotel-Information) [See all properties in Middlesex](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=553248635935228195&sort=VACATION_RENTAL) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## Check Middlesex hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635935228195&startDate=2026-02-13&endDate=2026-02-14)[Feb 13 - Feb 14](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635935228195&startDate=2026-02-13&endDate=2026-02-14) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635935228195&startDate=2026-02-14&endDate=2026-02-15)[Feb 14 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635935228195&startDate=2026-02-14&endDate=2026-02-15) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635935228195&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635935228195&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026) ### Popular places to visit #### Clarks Gully Commune with nature and explore the great outdoors at Clarks Gully during your travels in Middlesex. Stroll along this relaxing area's lakeside, or simply enjoy its wineries. [](https://expedia.com/Clarks-Gully-Middlesex.d553248621561241993.Vacation-Attraction) ## Cities near Middlesex ![Fall in Penn Yan New York](https://images.trvl-media.com/place/183705/58b3e219-265d-4343-aee0-b26443aedbf8.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Penn Yan ![Autumn in Naples, NY](https://images.trvl-media.com/place/6060357/8ba9cf8d-eb55-4218-978b-b77076cd7bfc.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Naples ![Marina panorama on Keuka Lake in Penn Yan, Finger Lakes region, New York. Amazing natural beauty. Late autumn season, so sailing season just ended](https://images.trvl-media.com/place/3000448059/6407ac85-b10a-420f-87b1-f0df54223a80.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Branchport ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Majestic Hills Golf Course ](https://www.expedia.com/Majestic-Hills-Golf-Course-Hotels.0-l553248621532664954-0.Travel-Guide-Filter-Hotels) - [Hotels near Clarks Gully ](https://www.expedia.com/Clarks-Gully-Hotels.0-l553248621561241993-0.Travel-Guide-Filter-Hotels) - [Hotels near Bristol Harbour Village ](https://www.expedia.com/Bristol-Harbour-Village-Canandaigua-Hotels.0-n553248635976473477-0.Travel-Guide-Filter-Hotels) - [Rushville Hotels ](https://www.expedia.com/Rushville-Hotels.d553248634998840024.Travel-Guide-Hotels) - [Hotels near Naples Community Park Disc Golf Course ](https://www.expedia.com/Naples-Community-Park-Disc-Golf-Course-Hotels.0-l553248621532664854-0.Travel-Guide-Filter-Hotels) - 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[Reservoir Creek Golf Course ](https://www.expedia.com/Reservoir-Creek-Golf-Course-Naples.d553248621532664850.Vacation-Attraction) - [Visit Bluff Point ](https://www.expedia.com/Bluff-Point.dx6034560) - [Visit Keuka Park ](https://www.expedia.com/Keuka-Park.dx6190620) - [Keuka Lake State Park ](https://www.expedia.com/Keuka-Lake-State-Park-Keuka-Park.d6217978.Vacation-Attraction) - [Visit Penn Yan ](https://www.expedia.com/Penn-Yan.dx183705) - [Keuka Park Vacations ](https://www.expedia.com/Keuka-Park.d6190620.Destination-Travel-Guides) - [Car rentals near Grange Landing ](https://www.expedia.com/Car-Rentals-In-Grange-Landing.d3000008402.Car-Rental-Guide) - [Car rentals near Bristol Mountain Ski Resort ](https://www.expedia.com/Car-Rentals-In-Bristol-Mountain-Ski-Resort.d553248621532664860.Car-Rental-Guide) - [Car rentals near Bristol Hills ](https://www.expedia.com/Car-Rentals-In-Bristol-Hills.d553248635975749345.Car-Rental-Guide) - [Car rentals near Naples ](https://www.expedia.com/Car-Rentals-In-Naples.d6060357.Car-Rental-Guide) - [Priceless Car Rental Rental Cars in Naples ](https://www.expedia.com/Priceless-Car-Rental-Car-Rentals-In-Naples.d6060357-c1060.Car-Rental-Guide-Suppliers) - [Car rentals near Bluff Point ](https://www.expedia.com/Car-Rentals-In-Bluff-Point.d6034560.Car-Rental-Guide) - [Car rentals near Keuka Lake State Park ](https://www.expedia.com/Car-Rentals-In-Keuka-Lake-State-Park.d6217978.Car-Rental-Guide) - [Car rentals near Keuka Park ](https://www.expedia.com/Car-Rentals-In-Keuka-Park.d6190620.Car-Rental-Guide) - [Grange Landing Vacation Rentals ](https://www.expedia.com/Grange-Landing-Vacation-Rentals.d3000008402.Travel-Guide-VacationRentals) - [Naples Vacation Rentals ](https://www.expedia.com/Naples-Vacation-Rentals.d6060357.Travel-Guide-VacationRentals) - [Bluff Point Vacation Rentals ](https://www.expedia.com/Bluff-Point-Vacation-Rentals.d6034560.Travel-Guide-VacationRentals) - [Keuka Park Vacation Rentals ](https://www.expedia.com/Keuka-Park-Vacation-Rentals.d6190620.Travel-Guide-VacationRentals) - [Things to do in Naples ](https://www.expedia.com/Things-To-Do-In-Naples.d6060357.Travel-Guide-Activities) - Cities near Middlesex - Places of interest [Penn Yan](https://expedia.com/Penn-Yan.dx183705)[Naples](https://expedia.com/Naples.dx6060357)[Branchport](https://expedia.com/Branchport.dx3000448059) - [Clarks Gully ](https://expedia.com/Clarks-Gully-Middlesex.d553248621561241993.Vacation-Attraction) - [Keuka Lake ](https://expedia.com/Keuka-Lake-New-York.d553248635056399260.Vacation-Attraction) - [CMAC Performing Arts Center ](https://expedia.com/CMAC-Performing-Arts-Center-Canandaigua.d553248621532664960.Vacation-Attraction) - [Bristol Mountain Ski Resort ](https://expedia.com/Bristol-Mountain-Ski-Resort-Canandaigua.d553248621532664860.Vacation-Attraction) - [Hobart and William Smith Colleges ](https://expedia.com/Hobart-And-William-Smith-Colleges-Geneva.d6211480.Vacation-Attraction) - [Three Brothers Wineries and Estates ](https://expedia.com/Three-Brothers-Wineries-And-Estates-Geneva.d6211533.Vacation-Attraction) - [Finger Lakes Gaming and Racetrack ](https://expedia.com/Finger-Lakes-Gaming-And-Racetrack-Farmington.d553248621532664910.Vacation-Attraction) - [Seneca Lake State Park ](https://expedia.com/Seneca-Lake-State-Park-Geneva.d6211502.Vacation-Attraction) - [Sampson State Park ](https://expedia.com/Sampson-State-Park-Romulus.d6214967.Vacation-Attraction) - [Honeoye Lake ](https://expedia.com/Honeoye-Lake-Honeoye.d553248635976196808.Vacation-Attraction) - [Keuka Lake Outlet Trail ](https://expedia.com/Keuka-Lake-Outlet-Trail-Penn-Yan.d553248635942937924.Vacation-Attraction) - [Keuka Lake State Park ](https://expedia.com/Keuka-Lake-State-Park-Keuka-Park.d6217978.Vacation-Attraction) - [Roseland Waterpark ](https://expedia.com/Roseland-Waterpark-Canandaigua.d6212309.Vacation-Attraction) - [Sonnenberg Gardens and Mansion State Historic Park ](https://expedia.com/Sonnenberg-Gardens-And-Mansion-State-Historic-Park-Canandaigua.d553248621532665056.Vacation-Attraction) - [Ventosa Vineyards ](https://expedia.com/Ventosa-Vineyards-Geneva.d6211602.Vacation-Attraction) - [Keuka Lake Vineyards ](https://expedia.com/Keuka-Lake-Vineyards-Hammondsport.d553248621532665001.Vacation-Attraction) - [Bully Hill Vineyards ](https://expedia.com/Bully-Hill-Vineyards-Hammondsport.d6217976.Vacation-Attraction) - [Fox Run Vineyards ](https://expedia.com/Fox-Run-Vineyards-Penn-Yan.d6087217.Vacation-Attraction) - [South Main Street ](https://expedia.com/South-Main-Street-Geneva.d6337530.Vacation-Attraction) - [Hermann J. Wiemer Vineyard ](https://expedia.com/Hermann-J-Wiemer-Vineyard-Dundee.d553248621532664963.Vacation-Attraction) - [Keuka College ](https://expedia.com/Keuka-College-New-York.d6087199.Vacation-Attraction) - [The Windmill Farm & Craft Market ](https://expedia.com/The-Windmill-Farm-Craft-Market-Penn-Yan.d553248633962925469.Vacation-Attraction) - [Kershaw Park ](https://expedia.com/Kershaw-Park-Canandaigua.d553248621555471526.Vacation-Attraction) - [Ravines Wine Cellars on Seneca Lake ](https://expedia.com/Ravines-Wine-Cellars-On-Seneca-Lake-Geneva.d553248621532664961.Vacation-Attraction) - [Finger Lakes Boating Museum ](https://expedia.com/Finger-Lakes-Boating-Museum-Hammondsport.d553248621561241988.Vacation-Attraction) - [Hill Cumorah Visitors Center ](https://expedia.com/Hill-Cumorah-Visitors-Center-Shortsville.d553248621555520549.Vacation-Attraction) - [Wagner Vineyards ](https://expedia.com/Wagner-Vineyards-Lodi.d553248621532664970.Vacation-Attraction) - [Canandaigua City Pier ](https://expedia.com/Canandaigua-City-Pier-New-York.d553248621561873473.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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