Middlesex Vacation Rentals

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Vacation Rentals in Middlesex

Birchwood Cottage, 200ft of Lake Beach-Fully flat lot -Private Driveway

Branchport NY

With a stay at this vacation home in Branchport, you'll be on the waterfront, within a 10-minute drive of Keuka Lake and Hunt Country Vineyards.

Naples Valley Getaway-Private home with hot tub.

Naples NY

Located in Naples, this vacation home is in a rural location, within a 5-minute drive of Reservoir Creek Golf Course and Bristol Valley Theater.

OnTheWater Romantic Cabin-Breathtakng View-Beach Fire Pit!-Still Aval Sep-Oct'26

Hammondsport NY

$721 nightly

$808 total

Sep 10 - Sep 11

Total with taxes and fees

When you stay at this vacation home in Hammondsport, you'll be on the beach, just steps from Keuka Lake and 7 minutes by foot from Ravines Wine Cellars.

Private Keuka Lake Access | Dock | FLX Wineries

Pen Yann NY

With a stay at this vacation home in Penn Yan, you'll be on a lake, within a 10-minute drive of Keuka Lake and Keuka Lake State Park.

Mission small group

Conesus NY

When you stay at this vacation home in Conesus, you'll be 14 minutes by car from Hemlock Fair.

Secluded Keuka Hills Cabin | Pond | Pet Friendly

Branchport NY

Located in Branchport, this vacation home is in a rural location, within a 15-minute drive of Italy Town Hall and Hunt Country Vineyards.

Kitchen

Washer

A quaint stay in wine country!

Hammondsport NY

With a stay at this vacation home in Hammondsport, you'll be on a lake, within a 10-minute drive of Keuka Lake and Point of the Bluff Vineyards.

2-bedroom vacation home in Hammondsport near Keuka Lake

Hammondsport NY

With a stay at this vacation home in Hammondsport, you'll be within a 5-minute drive of Keuka Lake and Glenn H. Curtiss Museum.

Coach-ella on the Lake - Ideal Canandaigua Lake Couples Retreat!

Canandaigua NY

With a stay at this vacation home in Canandaigua, you'll be on a lake, within a 10-minute drive of Canandaigua Lake and UR Medicine - F.F. Thompson Hospital.

Entire House with private lake access and hot tub! Near local ski resorts!!

Honeoye NY

Located in Honeoye, this vacation home is on a lake, within a 5-minute drive of Sandy Bottom Park and Honeoye Lake.

The Willow-Seneca Lake-Countryside-Hot Tub-Wine Trail - Pets, Across Road From Wiemer Vineyard

Starkey NY

When you stay at this vacation home in Dundee, you'll be on a lake, within a 10-minute walk of Seneca Lake and Hermann J. Wiemer Vineyard.

Paradise on the Lake

Rushville NY

With a stay at this vacation home in Rushville, you'll be on the waterfront, just steps from Canandaigua Lake.

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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.