Book Hotels in Middlesex, NY

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Top Middlesex hotels

Best Western Plus Vineyard Inn & Suites

Best Western Plus Vineyard Inn & Suites

2.5 out of 5
142 Lake St Penn Yan NY
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $101 total per night from Nov 1 to Nov 2
$101 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. A 24-hour business center, ...
"The hotel and grounds were so well taken care of, it was a delight to stay there! The staff was mostly friendly and the location was close to downtown attractions. My biggest complaint is there's only one elevator and it's at the far end of the corridor, not centrally located. You get a bit of a ..."

Reviewed on Oct 4, 2026

Opens in a new windowBest Western Plus Vineyard Inn & Suites
Best Western Plus The Hammondsport Hotel

Best Western Plus The Hammondsport Hotel

2.5 out of 5
8440 State Route 54 Hammondsport NY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Nov 1 to Nov 2
$113 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
"Breakfast was good. Staff was helpful & nice."

Reviewed on Oct 3, 2026

Opens in a new windowBest Western Plus The Hammondsport Hotel
Hampton Inn Penn Yan

Hampton Inn Penn Yan

2.5 out of 5
110 Mace Street Penn Yan NY
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $86 total per night from Nov 1 to Nov 2
$86 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Enjoy the gym and free perks like buffet breakfast and free self parking. A 24-hour business ...
"Everything was great"

Reviewed on Oct 2, 2026

Opens in a new windowHampton Inn Penn Yan
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
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Nov 1 to Nov 2
$84 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"Traveled to Penn Yan for a wedding and only needed a room for the night. Booked an early check in and they waived the fee. They also let me do a late check out at the last minute. Very close to all the main restaurants in the area. You can literally keep your car parked at the hotel and walk. No ..."

Reviewed on Oct 4, 2026

Opens in a new windowMicrotel by Wyndham Penn Yan Finger Lakes Region
41 Lakefront Hotel, Trademark Collection By Wyndham

41 Lakefront Hotel, Trademark Collection By Wyndham

3 out of 5
41 Lake Front Blvd Geneva NY
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $110 total per night from Nov 3 to Nov 4
$110 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax ...
"Outdated, pool was not usable looked like a green hot tub. One staff member at the front desk was dressed in sloppy, casual clothes and unshaven also not overly friendly. The room was not super clean and the entire building needs some renovations. I would not recommend and I will not go back. On ..."

Reviewed on Oct 4, 2026

Opens in a new window41 Lakefront Hotel, Trademark Collection By Wyndham
Showboat Hotel

Showboat Hotel

2 out of 5
3434 N Plum Point Rd Himrod NY
$117 nightly
The price is $131 total per night from Oct 8 to Oct 9
$131 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Free self parking, a coffee shop, and a snack bar/deli are also offered.
"The deck at the restaurant is fantastic. The room I stayed in was small but pretty clean. Seemed like a fair deal. There were no staff on site but someone was helpful by phone and text. Stay for the view."

Reviewed on Oct 4, 2026

Opens in a new windowShowboat Hotel
The Lake House on Canandaigua

The Lake House on Canandaigua

4.5 out of 5
770 South Main Street Canandaigua NY
Fully refundableReserve now, pay when you stay
$318 nightly
The price is $361 total per night from Oct 29 to Oct 30
$361 total
Oct 29 - Oct 30
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...
Opens in a new windowThe Lake House on Canandaigua
Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton

3.5 out of 5
205 Lakeshore Drive Canandaigua NY
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $191 total per night from Oct 28 to Oct 29
$191 total
Oct 28 - Oct 29
Total with taxes and fees
The hotel's outdoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Enjoy the hot tub and perks like free WiFi. A restaurant, a 24-hour ...
Opens in a new windowHotel Canandaigua, Tapestry Collection by Hilton
Holiday Inn Express Canandaigua - Finger Lakes by IHG

Holiday Inn Express Canandaigua - Finger Lakes by IHG

2.5 out of 5
330 Eastern Blvd. Canandaigua NY
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $122 total per night from Nov 3 to Nov 4
$122 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
Opens in a new windowHoliday Inn Express Canandaigua - Finger Lakes by IHG
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See all available properties in Middlesex
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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.

Frequently asked questions

What are the top kid-friendly hotels in Middlesex?
From cool amenities to extra space, kid-friendly hotels are equipped with features that can help turn a great family vacation into an awesome one. These Middlesex properties make traveling with children easy: Unpack your bags at Aunt Als Place w/ Private Deck & Fire Pit!. It comes with a nearby beach, a barbecue grill and a talent for making families feel at home. Also check out the deals at Private getaway cabin in the woods. It offers a firepit, a fireplace and plenty of opportunities to hang out together.
Where can I find cheap hotels in Middlesex?
At Travelocity you'll find really nice hotels in Middlesex at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Middlesex rather than in Middlesex. We may find you even better rates, too.
How do I find the best Middlesex hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Middlesex then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Middlesex?
The cheapest hotel in Middlesex is $84. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Middlesex?
There are 1,475 hotels in Middlesex on Travelocity.
What are the best hotels in Middlesex?
Middlesex has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Middlesex for you!
When is the best time to visit Middlesex?
If you want the joy of a fun-filled trip in peak season, visit Middlesex during March, August and September. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Middlesex?
Based on historic data is usually the cheapest month to visit Middlesex. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Middlesex?
There are multiple hotels in Middlesex that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Middlesex. We have plenty of kid-friendly hotels in Middlesex to choose from on Travelocity!
Why book a hotel in Middlesex through Travelocity?
Because we have the top hotels in Middlesex! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Middlesex on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Middlesex hotel reviews by fellow wanderers

Microtel Inn & Suites by Wyndham Farmington

Microtel Inn & Suites by Wyndham Farmington

5 out of 5
Posted 10 hours ago
Travelocity Verified Review
"The hotel is conveniently located. Clean and well maintained. Breakfast is continental. There are waffles which are good, though I usually just eat a bagel. Always a good experience. I have a small dog and she loves the walking area."
A verified traveler stayed at Microtel Inn & Suites by Wyndham Farmington
Microtel Inn & Suites by Wyndham Farmington

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