Middlesex, NY

Travel Guide

A waterfall cascading through a narrow rock formation surrounded by greenery.
41 Lakefront Hotel, Trademark Collection By Wyndham

41 Lakefront Hotel, Trademark Collection By Wyndham

3 out of 5
41 Lake Front Blvd Geneva NY
$143 nightly
The price is $162 total per night from Sep 27 to Sep 28
$162 total
Sep 27 - Sep 28
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 ...
41 Lakefront Hotel, Trademark Collection By Wyndham
The Lake House on Canandaigua

The Lake House on Canandaigua

4.5 out of 5
770 South Main Street Canandaigua NY
Fully refundable
$356 nightly
The price is $404 total per night from Oct 14 to Oct 15
$404 total
Oct 14 - Oct 15
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 ...
The Lake House on Canandaigua
Microtel by Wyndham Penn Yan Finger Lakes Region

Microtel by Wyndham Penn Yan Finger Lakes Region

3 out of 5
124 Elm St Penn Yan NY
$107 nightly
The price is $120 total per night from Sep 27 to Sep 28
$120 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Penn Yan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,001 reviews)
"Mold in the tub. Nowhere to hang towels. Pool cloudy and over chlorinated. No room service at all. Breakfast was very nice. Young man at evening desk duty very nice."

Reviewed on Sep 22, 2026

Microtel by Wyndham Penn Yan Finger Lakes Region
See all 1,475 properties in Middlesex
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.
Modern waterfront cottage on Keuka Lake - close to Penn Yan & Finger Lakes wine!

Modern waterfront cottage on Keuka Lake - close to Penn Yan & Finger Lakes wine!

Penn Yan NY
Stay at this cottage in Penn Yan. Enjoy free WiFi, laundry facilities, and patios. Popular attractions The Windmill Farm & Craft Market and Keuka Lake State ...
9.6/10 Exceptional! (152 reviews)
"Clean dog friendly space with everything we needed. Highly recommend!"

Reviewed on Sep 20, 2026

Modern waterfront cottage on Keuka Lake - close to Penn Yan & Finger Lakes wine!
Seneca Hideaway/Sunken Vessel/Hot Tub

Seneca Hideaway/Sunken Vessel/Hot Tub

Geneva NY
Stay at this cabin in Geneva. Enjoy free WiFi, a fitness center, and an in-room coffeemaker. Popular attractions Ravines Wine Cellars on Seneca Lake and Lacey ...
9.6/10 Exceptional! (15 reviews)
"This was a great place to stay! Close to everything. Hosts were awesome and quick to respond!"

Reviewed on Aug 30, 2026

Seneca Hideaway/Sunken Vessel/Hot Tub
THE GRAPE ESCAPE - PET FRIENDLY! - OFF GRID - ROMANTIC LAKE VIEW - ON WINE TRAIL

THE GRAPE ESCAPE - PET FRIENDLY! - OFF GRID - ROMANTIC LAKE VIEW - ON WINE TRAIL

Hammondsport NY
Stay at this cabin in Hammondsport. Enjoy an in-room coffeemaker. Popular attractions Bully Hill Vineyards and Keuka Lake Vineyards are located nearby.
9.8/10 Exceptional! (79 reviews)
"Everything was convenient and cozy close to town w plenty to do, only complaint was the shower"

Reviewed on Sep 7, 2026

THE GRAPE ESCAPE - PET FRIENDLY! - OFF GRID - ROMANTIC LAKE VIEW - ON WINE TRAIL
See all properties in Middlesex
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.

Stay near popular Middlesex attractions

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.
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Frequently asked questions

Is Middlesex worth visiting?
Middlesex is worth visiting for its natural beauty, highlighted by Clarks Gully, and a diverse culinary scene. Travelers can enjoy a range of Italian and European dining options, from classic pasta dishes to various European specialties.
When is the best time to visit Middlesex?
The best time to visit Middlesex is from May through September, when the weather is generally pleasant for exploring. For travelers seeking fewer crowds and better value, the quieter months of December through March are a good alternative, offering cooler temperatures.
What is Middlesex known for?
Middlesex is known for being home to Clarks Gully. Travelers can also find a strong Italian food culture in this city.
What is a good itinerary length for Middlesex?
A good itinerary length for Middlesex is one to two days to explore Clarks Gully and enjoy the local Italian, European, or Asian dining. An extended stay of two to three days allows for more relaxed exploration of Clarks Gully and trying out different culinary experiences.
What are the top things to do in and around Middlesex?
In Middlesex, explore Clarks Gully, a natural point of interest.
What cuisines can you find in Middlesex?
In Middlesex you can find Italian cuisine, offering classics like pasta, pizza, risotto, and tiramisu. Travelers can also explore European Mediterranean options, along with Asian Chinese, Latin American, and North American dishes, providing a wide range of flavors.
Can I book a refundable hotel in Middlesex?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Middlesex by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Middlesex with Expedia?
Expedia makes it easier to plan your Middlesex trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Middlesex?
The best choice depends on your travel style. Hotels in Middlesex can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Middlesex trip on Expedia?
Once you've booked your Middlesex trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Middlesex trip?
Expedia offers customer support before, during, and after your Middlesex trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Middlesex?
If it's your first trip to Middlesex, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Middlesex hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Middlesex hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Middlesex

A lake with boats, a white house with columns, and a smaller building on a grassy hill.

Penn Yan

A coastal city with a marina filled with boats, a prominent mountain in the background, and a mix of historic and modern buildings along the waterfront.

Naples

A marina with multiple docks extending into a calm lake, surrounded by trees and buildings.

Branchport

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