Photo by Matthew Jay

Find Hotels with a Pool in Middlesex, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Middlesex Hotels with a Pool

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Middlesex hotels with a pool

Indoor pool
Hampton Inn Penn Yan

Hampton Inn Penn Yan

Hampton Inn Penn Yan
2.5 star property
Penn Yan
9.4 out of 10, Exceptional, (1002)
"Our room was very clean, breakfast was great, and the staff was super friendly and very accommodating! Will definitely go back!"
United States
Robin
The price is NT$2,250
NT$2,520 total
includes taxes & fees
Dec 29 - Dec 30
Hampton Inn Penn Yan
Indoor pool
Microtel by Wyndham Penn Yan Finger Lakes Region

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)
"Clean room, great location. Friendly staff"
United States
Jamie
The price is NT$2,468
NT$2,764 total
includes taxes & fees
Jan 12 - 2026/1/13
Microtel by Wyndham Penn Yan Finger Lakes Region
Indoor pool
Best Western Plus Vineyard Inn & Suites

Best Western Plus Vineyard Inn & Suites

Best Western Plus Vineyard Inn & Suites
2.5 star property
Penn Yan
9.6 out of 10, Exceptional, (1004)
"Room was great and so was staff"
United States
Jennifer
The price is NT$2,654
NT$2,973 total
includes taxes & fees
Dec 29 - Dec 30
Best Western Plus Vineyard Inn & Suites
Indoor pool
Holiday Inn Express Canandaigua - Finger Lakes by IHG

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)
"Hotel is always clean. Staff is always welcoming and the food is always great. "
United States
Heather
The price is NT$2,651
NT$2,930 total
includes taxes & fees
Jan 4 - 2026/1/5
Holiday Inn Express Canandaigua - Finger Lakes by IHG
Indoor pool
Comfort Inn & Suites Farmington - Victor

Comfort Inn & Suites Farmington - Victor

Comfort Inn & Suites Farmington - Victor
2.5 star property
Farmington
8.8 out of 10, Excellent, (1002)
"Parking is free, and was near everything. "
United States
Lisha
The price is NT$2,759
NT$3,049 total
includes taxes & fees
Jan 4 - 2026/1/5
Comfort Inn & Suites Farmington - Victor
Indoor pool
41 Lakefront Hotel, Trademark Collection By Wyndham

41 Lakefront Hotel, Trademark Collection By Wyndham

41 Lakefront Hotel, Trademark Collection By Wyndham
3.0 star property
Geneva
8.4 out of 10, Very Good, (1087)
"Room was very clean and spacious."
United States
Ann
The price is NT$3,266
NT$3,707 total
includes taxes & fees
Jan 8 - 2026/1/9
41 Lakefront Hotel, Trademark Collection By Wyndham
Indoor pool
Fairfield Inn & Suites by Marriott Geneva Finger Lakes

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)
"Super clean, great breakfast and friendly staff!"
United States
Lynne
The price is NT$2,924
NT$3,319 total
includes taxes & fees
Jan 6 - 2026/1/7
Fairfield Inn & Suites by Marriott Geneva Finger Lakes
Seasonal outdoor pool, pool umbrellas, sun loungers
Geneva On The Lake

Geneva On The Lake

Geneva On The Lake
3.0 star property
Geneva
8.8 out of 10, Excellent, (307)
"It was a wonderful stay in a historical inn with an excellent restaurant and bar. Beautiful water view and immaculately maintained grounds. Very clean room and attentive staff. Would definitely come here again. "
United States
John
Geneva On The Lake
Indoor pool
Hampton Inn Geneva

Hampton Inn Geneva

Hampton Inn Geneva
2.5 star property
Geneva
8.4 out of 10, Very Good, (730)
"Property location great. "
United States
Gail
The price is NT$3,080
NT$3,496 total
includes taxes & fees
Dec 29 - Dec 30
Hampton Inn Geneva
Outdoor pool, open 7:00 AM to 10:00 AM, pool umbrellas, sun loungers
Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton
3.5 star property
Canandaigua
9.0 out of 10, Wonderful, (301)
"Beds are so comfy and hotel is really upscale - overlooking beautiful Canandaigua Lake. "
United States
Hilarie
The price is NT$4,384
NT$4,976 total
includes taxes & fees
Dec 29 - Dec 30
Hotel Canandaigua, Tapestry Collection by Hilton
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.
View all properties

Top Middlesex Hotel Reviews

Best Western Plus Vineyard Inn & Suites

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."
Emma 1-night trip
Posted 3 days ago
Best Western Plus Vineyard Inn & Suites

Frequently asked questions

What are some hotels with pools in Middlesex?
The Lake House on Canandaigua: Features 2 restaurants, an outdoor pool, and a full-service spa. Hotel Canandaigua, Tapestry Collection by Hilton: Offers 2 bars, a seasonal outdoor pool, and a snack bar/deli. Microtel Inn & Suites by Wyndham Farmington: Features free self parking, an indoor pool, and complimentary wireless internet access. 41 Lakefront Hotel, Trademark Collection By Wyndham: Offers free self parking, an outdoor pool, and flat-screen televisions. Plum Point Lodge: Features buffet, an indoor pool, and complimentary wired internet access.
What is there to see and do in Middlesex?
Spend some time experiencing the great outdoors at Canandaigua Lake and Clarks Gully. Discover sights such as West River Marsh during your stay.
When is the best time to book a hotel with a pool in Middlesex?
Taking into account the local weather in Middlesex is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Middlesex are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.