Photo by Matthew Jay
Hotels in Middlesex
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The Naples Hotel
The Naples Hotel
3.0 star property
Naples
9.4 out of 10, Exceptional, (87)
9.4/10
Exceptional
(87)
- Unwind in a golf hotel just minutes from Canandaigua Lake in scenic Naples.
The price is $219
$219
$242 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Penn Yan
Hampton Inn Penn Yan
2.5 star property
Penn Yan
9.4 out of 10, Exceptional, (1002)
9.4/10
Exceptional
(1002)
The price is $71
$71
$80 total
includes taxes & fees
Dec 28 - Dec 29
Microtel by Wyndham Penn Yan Finger Lakes Region
Microtel by Wyndham Penn Yan Finger Lakes Region
3.0 star property
Penn Yan
8.8 out of 10, Excellent, (1001)
8.8/10
Excellent
(1001)
- A lakeside retreat with an indoor pool near Keuka Lake in the Finger Lakes region.
The price is $79
$79
$89 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Sutherland House Victorian Bed & Breakfast
Sutherland House Victorian Bed & Breakfast
4.0 star property
Canandaigua
9.8 out of 10, Exceptional, (139)
9.8/10
Exceptional
(139)
The price is $143
$143
$158 total
includes taxes & fees
Dec 21 - Dec 22
Chalet of Canandaigua
Chalet of Canandaigua
3.5 star property
Canandaigua
9.4 out of 10, Exceptional, (354)
9.4/10
Exceptional
(354)
- Surrounded by skiing adventures, this cozy B&B offers a perfect Canandaigua retreat.
The price is $389
$389
$418 total
includes taxes & fees
Dec 29 - Dec 30
Best Western Plus Vineyard Inn & Suites
Best Western Plus Vineyard Inn & Suites
2.5 star property
Penn Yan
9.6 out of 10, Exceptional, (1003)
9.6/10
Exceptional
(1003)
The price is $84
$84
$94 total
includes taxes & fees
Dec 28 - Dec 29
Holiday Inn Express Canandaigua - Finger Lakes by IHG
Holiday Inn Express Canandaigua - Finger Lakes by IHG
2.5 star property
Canandaigua
8.6 out of 10, Excellent, (1001)
8.6/10
Excellent
(1001)
- Stay near Canandaigua Lake with a fitness center and indoor pool for year-round fun.
The price is $88
$88
$97 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Econo Lodge Inn & Suites Canandaigua - Fingers Lake Area
Econo Lodge Inn & Suites Canandaigua - Fingers Lake Area
2.0 star property
Canandaigua
7.6 out of 10, Good, (488)
7.6/10
Good
(488)
- Tranquil Finger Lakes getaway offers hot tub relaxation and helpful staff service.
The price is $77
$77
$85 total
includes taxes & fees
Dec 28 - Dec 29
Los Gatos Bed & Breakfast
Los Gatos Bed & Breakfast
3.0 star property
Penn Yan
9.4 out of 10, Exceptional, (443)
9.4/10
Exceptional
(443)
- Enjoy a tranquil retreat on Keuka Lake with hiking trails and free gourmet breakfast.
The price is $189
$189
$212 total
includes taxes & fees
Dec 21 - Dec 22
The Lake House on Canandaigua
The Lake House on Canandaigua
4.5 star property
Canandaigua
9.4 out of 10, Exceptional, (433)
9.4/10
Exceptional
(433)
- Seasonal sanctuary at the water's edge with winter thrills and luxe spa amenities.
The price is $241
$241
$317 total
includes taxes & fees
Dec 24 - Dec 25
Hotel Canandaigua, Tapestry Collection by Hilton
Hotel Canandaigua, Tapestry Collection by Hilton
3.5 star property
Canandaigua
9.0 out of 10, Wonderful, (301)
9.0/10
Wonderful
(301)
- Lakeside retreat with modern amenities near Kershaw Park and Roseland Waterpark.
The price is $139
$139
$158 total
includes taxes & fees
Dec 29 - Dec 30
Super 8 by Wyndham Canandaigua
Super 8 by Wyndham Canandaigua
2.5 star property
Canandaigua
6.6 out of 10, (1000)
6.6/10
(1000)
- Comfy motel near Roseland Waterpark with free WiFi and convenient parking.
The price is $81
$81
$89 total
includes taxes & fees
Dec 28 - Dec 29
Canandaigua Guesthouse
Canandaigua Guesthouse
4.0 star property
Canandaigua
10.0 out of 10, Exceptional, (13)
10/10
Exceptional
(13)
The price is $247
$247
$280 total
includes taxes & fees
Dec 21 - Dec 22
B&B at Oliver Phelps
B&B at Oliver Phelps
4.0 star property
Canandaigua
9.2 out of 10, Wonderful, (315)
9.2/10
Wonderful
(315)
- Stay at this charming B&B in Canandaigua, with free breakfast and nearby museums.
The price is $215
$215
$244 total
includes taxes & fees
Dec 30 - Dec 31
White Springs Manor a Belhurst Property
White Springs Manor a Belhurst Property
3.5 star property
Geneva
8.2 out of 10, Very Good, (321)
8.2/10
Very Good
(321)
- Take in Geneva's rich history in a romantic manor with a full-service spa.
The price is $109
$109
$120 total
includes taxes & fees
Dec 21 - Dec 22
Microtel Inn & Suites by Wyndham Geneva
Microtel Inn & Suites by Wyndham Geneva
2.0 star property
Geneva
8.6 out of 10, Excellent, (1002)
8.6/10
Excellent
(1002)
- Experience a Finger Lakes getaway with proximity to local vineyards and wineries.
The price is $89
$89
$99 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites Geneva Finger Lakes by IHG
Holiday Inn Express & Suites Geneva Finger Lakes by IHG
2.5 star property
Geneva
9.2 out of 10, Wonderful, (1001)
9.2/10
Wonderful
(1001)
- Scenic Geneva escape with indoor pool, near Ravines Wine Cellars on Seneca Lake.
The price is $105
$105
$116 total
includes taxes & fees
Dec 28 - Dec 29
Days Inn by Wyndham Geneva/Finger Lakes
Days Inn by Wyndham Geneva/Finger Lakes
2.0 star property
Geneva
7.2 out of 10, Good, (1000)
7.2/10
Good
(1000)
- Welcoming Finger Lakes motel with free on-the-go breakfast and peaceful ambiance.
The price is $73
$73
$81 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Fairfield Inn & Suites by Marriott Geneva Finger Lakes
Fairfield Inn & Suites by Marriott Geneva Finger Lakes
3.0 star property
Western Gardens
9.2 out of 10, Wonderful, (624)
9.2/10
Wonderful
(624)
- Tranquil lakeside lodging with indoor pool and complimentary amenities await.
The price is $93
$93
$105 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Geneva On The Lake
Geneva On The Lake
3.0 star property
Geneva
8.8 out of 10, Excellent, (307)
8.8/10
Excellent
(307)
- Discover a charming lakeside retreat with easy access to South Main Street attractions.
The price is $214
$214
$258 total
includes taxes & fees
Dec 28 - Dec 29
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.
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.
Budget hotels in Middlesex and vicinity
9.4 out of 10, Exceptional, (1002)
9.4/10
Exceptional
(1002)
The price is $71
$71
$80 total
includes taxes & fees
Dec 28 - Dec 29
Days Inn by Wyndham Geneva/Finger Lakes
Days Inn by Wyndham Geneva/Finger Lakes2.0 star property
Geneva
7.2 out of 10, Good, (1000)
7.2/10
Good
(1000)
The price is $73
$73
$81 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.4 out of 10, Very Good, (346)
8.4/10
Very Good
(346)
The price is $75
$75
$83 total
includes taxes & fees
Dec 21 - Dec 22
8.4 out of 10, Very Good, (469)
8.4/10
Very Good
(469)
The price is $76
$76
$84 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Econo Lodge Inn & Suites Canandaigua - Fingers Lake Area
Econo Lodge Inn & Suites Canandaigua - Fingers Lake Area2.0 star property
Canandaigua
7.6 out of 10, Good, (488)
7.6/10
Good
(488)
The price is $77
$77
$85 total
includes taxes & fees
Dec 28 - Dec 29
Microtel by Wyndham Penn Yan Finger Lakes Region
Microtel by Wyndham Penn Yan Finger Lakes Region3.0 star property
Penn Yan
8.8 out of 10, Excellent, (1001)
8.8/10
Excellent
(1001)
The price is $79
$79
$89 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Best Western Plus Vineyard Inn & Suites
Best Western Plus Vineyard Inn & Suites2.5 star property
Penn Yan
9.6 out of 10, Exceptional, (1003)
9.6/10
Exceptional
(1003)
The price is $84
$84
$94 total
includes taxes & fees
Dec 28 - Dec 29
Microtel Inn & Suites by Wyndham Farmington
Microtel Inn & Suites by Wyndham Farmington2.5 star property
Farmington
9.4 out of 10, Exceptional, (919)
9.4/10
Exceptional
(919)
The price is $84
$84
$93 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Comfort Inn & Suites Farmington - Victor
Comfort Inn & Suites Farmington - Victor2.5 star property
Farmington
8.8 out of 10, Excellent, (1002)
8.8/10
Excellent
(1002)
The price is $88
$88
$97 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Microtel Inn & Suites by Wyndham Geneva
Microtel Inn & Suites by Wyndham Geneva2.0 star property
Geneva
8.6 out of 10, Excellent, (1002)
8.6/10
Excellent
(1002)
The price is $89
$89
$99 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Canandaigua - Finger Lakes by IHG
Holiday Inn Express Canandaigua - Finger Lakes by IHG2.5 star property
Canandaigua
8.6 out of 10, Excellent, (1001)
8.6/10
Excellent
(1001)
The price is $88
$88
$97 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Best Western Plus The Hammondsport Hotel
Best Western Plus The Hammondsport Hotel2.5 star property
Hammondsport
9.6 out of 10, Exceptional, (1001)
9.6/10
Exceptional
(1001)
The price is $98
$98
$110 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Fairfield Inn & Suites by Marriott Geneva Finger Lakes
Fairfield Inn & Suites by Marriott Geneva Finger Lakes3.0 star property
Western Gardens
9.2 out of 10, Wonderful, (624)
9.2/10
Wonderful
(624)
The price is $93
$93
$105 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.4 out of 10, Very Good, (730)
8.4/10
Very Good
(730)
The price is $98
$98
$111 total
includes taxes & fees
Dec 28 - Dec 29
Holiday Inn Express & Suites Geneva Finger Lakes by IHG
Holiday Inn Express & Suites Geneva Finger Lakes by IHG2.5 star property
Geneva
9.2 out of 10, Wonderful, (1001)
9.2/10
Wonderful
(1001)
The price is $105
$105
$116 total
includes taxes & fees
Dec 28 - Dec 29
41 Lakefront Hotel, Trademark Collection By Wyndham
41 Lakefront Hotel, Trademark Collection By Wyndham3.0 star property
Geneva
8.4 out of 10, Very Good, (1086)
8.4/10
Very Good
(1086)
The price is $104
$104
$118 total
includes taxes & fees
Jan 1 - Jan 2, 2026
White Springs Manor a Belhurst Property
White Springs Manor a Belhurst Property3.5 star property
Geneva
8.2 out of 10, Very Good, (321)
8.2/10
Very Good
(321)
The price is $109
$109
$120 total
includes taxes & fees
Dec 21 - Dec 22
Sutherland House Victorian Bed & Breakfast
Sutherland House Victorian Bed & Breakfast4.0 star property
Canandaigua
9.8 out of 10, Exceptional, (139)
9.8/10
Exceptional
(139)
The price is $143
$143
$158 total
includes taxes & fees
Dec 21 - Dec 22
9.8 out of 10, Exceptional, (67)
9.8/10
Exceptional
(67)
The price is $119
$119
$133 total
includes taxes & fees
Dec 21 - Dec 22
Hotel Canandaigua, Tapestry Collection by Hilton
Hotel Canandaigua, Tapestry Collection by Hilton3.5 star property
Canandaigua
9.0 out of 10, Wonderful, (301)
9.0/10
Wonderful
(301)
The price is $139
$139
$158 total
includes taxes & fees
Dec 29 - Dec 30
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.
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.
Go beyond your typical stay in Middlesex
Pet friendly
Family friendly
Cottage
Learn more about Middlesex
Middlesex is well-known for its attractions such as Canandaigua Lake and Clarks Gully.
Photo by Matthew Jay
Open Photo by Matthew Jay
Check out reviews of Middlesex hotels guests love
Best Western Plus Vineyard Inn & Suites
10/10 Excellent
"Room was spacious and clean. Pool and hot tub were great. Bed was comfortable.
The hot food at breakfast wasn’t very fresh but it didnt seem like there was alot of people in the hotel so probably just not a busy enough breakfast to remake the hot food again. But the other options were still good and i still had a good breakfast. bagels, toast, muffins, yogurt and parafait toppings, cereal, etc.
24/7 juice and coffee. Walking distance to many bars, breweries and restaurants.
Great stay would stay again for sure."
Hampton Inn Penn Yan
10/10 Excellent
"We enjoyed our stay"
Microtel Inn & Suites by Wyndham Geneva
10/10 Excellent
"The Staff at the Front Desk was super friendly and welcoming. The room was super clean and comfortable."
Microtel by Wyndham Penn Yan Finger Lakes Region
10/10 Excellent
"Clean room, great location. Friendly staff"
Best Western Plus The Hammondsport Hotel
10/10 Excellent
"Staff at desk"
41 Lakefront Hotel, Trademark Collection By Wyndham
10/10 Excellent
"Room was very clean and spacious."
Americas Best Value Inn Farmington
10/10 Excellent
"Room was clean, bathroom was very clean and bed was comfortable. "
Microtel Inn & Suites by Wyndham Farmington
10/10 Excellent
"The staff were great. The room was very clean and set up well. Easy to get there. Overall excellent stay. "
Holiday Inn Express Canandaigua - Finger Lakes by IHG
10/10 Excellent
"clean room and very friendly staff"
Frequently asked questions
Can I book refundable hotels in Middlesex?
If you're looking for the flexibility to change your plans to Middlesex, most hotels provide refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Middlesex if I want a vacation rental instead of a hotel?
You'll find 13 vacation homes on our site. You can also consider one of the 8 cottages for your trip.
What will the weather in Middlesex be like during my visit?
The warmest months in Middlesex are usually July and August with an average temp of 67°F. January and February are the chilliest months when the average temp is 29°F. The rainiest months are July and June.
Why should I book my Middlesex hotel through Hotels.com?
There are plenty of reasons to book your Middlesex travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.