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Middlesex Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Middlesex

Dining
Year-round, beautiful, peaceful, lake front home on Canandaigua Lake.

Year-round, beautiful, peaceful, lake front home on Canandaigua Lake.

Middlesex
10.0 out of 10, Exceptional, (12)
"It was quiet, relaxing, and an amazing experience overall. Plenty of activities and things to do around the house and the neighborhood."
United States
Clarisa C.
The price is HK$964
HK$2,724 total
includes taxes & fees
23 Nov - 24 Nov
Year-round, beautiful, peaceful, lake front home on Canandaigua Lake.
1 bedroom, iron/ironing board, WiFi, bed sheets
Sub Level Effiency

Sub Level Effiency

Geneva
8.8 out of 10, Excellent, (6)
"A great place to stay "
United States
Patrick
The price is HK$504
HK$728 total
includes taxes & fees
16 Nov - 17 Nov
Sub Level Effiency
Fridge, microwave, oven, stovetop
The Geneva Getaway- remodeled apartment walking distance from downtown Geneva

The Geneva Getaway- remodeled apartment walking distance from downtown Geneva

Geneva
10.0 out of 10, Exceptional, (30)
"We enjoyed all of the amenities and cozy comfort of this getaway. Also great proximity to the lake with fun activities and dining options."
United States
Sue G.
The price is HK$661
HK$1,503 total
includes taxes & fees
7 Dec - 8 Dec
The Geneva Getaway- remodeled apartment walking distance from downtown Geneva
Dining
Hubbs Cellar at JS Hubbs Guest House

Hubbs Cellar at JS Hubbs Guest House

Hammondsport
10.0 out of 10, Exceptional, (7)
"Very clean, quiet and convenient. Host was very nice and easy to work with as was the check-in, check-out process."
United States
Todd B.
The price is HK$777
HK$2,158 total
includes taxes & fees
16 Nov - 17 Nov
Hubbs Cellar at JS Hubbs Guest House
Fridge, microwave, oven, stovetop
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

Canandaigua
10.0 out of 10, Exceptional, (79)
"Great for a short get away!"
United States
Jonathan H.
The price is HK$1,049
HK$1,980 total
includes taxes & fees
16 Nov - 17 Nov
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Property grounds
Million-dollar view of Seneca lake Pet friendly3 bedroom ON water

Million-dollar view of Seneca lake Pet friendly3 bedroom ON water

Geneva
9.4 out of 10, Exceptional, (114)
"Great place, with awesome views and water access. Place was very comfortable"
United States
Laurie K.
Million-dollar view of Seneca lake Pet friendly3 bedroom ON water
2 bedrooms, WiFi
The Macberns Row House (Unit 1)

The Macberns Row House (Unit 1)

2.0 star property
Geneva
8.4 out of 10, Very good, (6)
"The set up of the unit was a bit strange, finding privacy for everyone in our family was difficult. The overall stay was good as it was just a night. Any longer than that would not have worked. "
United States
Chad
The price is HK$1,949
HK$3,332 total
includes taxes & fees
14 Nov - 15 Nov
The Macberns Row House (Unit 1)
Microwave, oven, stovetop, dishwasher
Lakeview and relax at the heart of Seneca lake

Lakeview and relax at the heart of Seneca lake

Geneva
9.6 out of 10, Exceptional, (9)
"Minor snafu when we first arrived but it was quickly remedied by the host. Property was in a good location and I would stay with this host again. "
United States
John C.
The price is HK$2,246
HK$4,135 total
includes taxes & fees
15 Nov - 16 Nov
Lakeview and relax at the heart of Seneca lake
Fridge, microwave, oven, stovetop
Chic Lakeview Getaway on Seneca Lake Wine Trail

Chic Lakeview Getaway on Seneca Lake Wine Trail

2.0 star property
Penn Yan
10.0 out of 10, Exceptional, (2)
"Beautiful area. Enjoyed Lake Seneca, wine country in Keuka Lake area, an Amish Country store and very good food at Casa Mezcal "
United States
Ellen G.
The price is HK$1,632
HK$3,402 total
includes taxes & fees
16 Nov - 17 Nov
Chic Lakeview Getaway on Seneca Lake Wine Trail
Exterior
Top of the Fingerlakes, relaxing retreat.

Top of the Fingerlakes, relaxing retreat.

Waterloo
9.8 out of 10, Exceptional, (26)
"Very comfortable, clean, and felt like home. Will be booking here again in June."
United States
April
The price is HK$902
HK$1,528 total
includes taxes & fees
16 Nov - 17 Nov
Top of the Fingerlakes, relaxing retreat.
Outdoor dining
Cozy, romantic getaway on a quiet Finger Lake

Cozy, romantic getaway on a quiet Finger Lake

Honeoye
9.8 out of 10, Exceptional, (27)
"Loved the area and the loft was nice and cozy."
United States
Anthony F.
The price is HK$657
HK$1,166 total
includes taxes & fees
16 Nov - 17 Nov
Cozy, romantic getaway on a quiet Finger Lake
Microwave, oven, stovetop
Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva

Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva

Geneva
9.0 out of 10, Wonderful, (17)
"Great property, within walking distance of lots of great restaurants and of course the lake front. Host was friendly and communicative. Would definitely stay again!"
United States
Jessica H.
The price is HK$944
HK$1,473 total
includes taxes & fees
15 Nov - 16 Nov
Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva
Fridge, microwave, oven, stovetop
Canandaigua House

Canandaigua House

Canandaigua
8.6 out of 10, Excellent, (17)
"We stayed at this house for my son‘s graduation from RIT. It offered us the perfect place to decompress. It was an easy commute back-and-forth to Rochester. However, the town offered many great sites to see and places to eat. We truly enjoyed the stay!!"
United States
Margaret S.
The price is HK$738
HK$2,356 total
includes taxes & fees
24 Nov - 25 Nov
Canandaigua House
Interior
Modern Studio APT in the Heart of Downtown Geneva

Modern Studio APT in the Heart of Downtown Geneva

Geneva
10.0 out of 10, Exceptional, (9)
"Apartment is walking distance to lake, restaurants and shops. Property owner replies to questions and concerns promptly. "
United States
Mary T.
The price is HK$957
HK$2,114 total
includes taxes & fees
16 Nov - 17 Nov
Modern Studio APT in the Heart of Downtown Geneva
Interior
The Nautilus at JS Hubbs Guest House

The Nautilus at JS Hubbs Guest House

Hammondsport
10.0 out of 10, Exceptional, (3)
"Walter was fantastic! We had a wonderful stay and will be back!!"
United States
Katherine F.
The price is HK$1,671
HK$3,333 total
includes taxes & fees
15 Nov - 16 Nov
The Nautilus at JS Hubbs Guest House
Exterior
Conesus Log Cabin, Cozy Log Cabin on the Wine Trail

Conesus Log Cabin, Cozy Log Cabin on the Wine Trail

Geneva
10.0 out of 10, Exceptional, (5)
"The rental is beautiful and in a great location. There were 6 of us. We had plenty of space. Amy (host) communicated all the info we needed in a very manner and answered our questions quickly. I would highly recommend this host and rental."
United States
Kim S.
The price is HK$2,992
HK$4,753 total
includes taxes & fees
16 Nov - 17 Nov
Conesus Log Cabin, Cozy Log Cabin on the Wine Trail
2 bedrooms, iron/ironing board, WiFi, bed sheets
The Wheat House on Main (Unit 5)

The Wheat House on Main (Unit 5)

Geneva
8.6 out of 10, Excellent, (8)
"The unit was very clean and neat and a very nice neighborhood with less than a half mile walk to downtown. The only downsides were no microwave or dishwasher, and only one frying pan plus it is adjacent to a busy road with lots of trucks so it was difficult to sit outside and chat. However with the air conditioner running and comfortable beds, we could not hear the noise and slept well. Also, heads up that the master bedroom is essentially the living room as well so anyone staying in the second...
United States
peg h.
The price is HK$1,453
HK$2,532 total
includes taxes & fees
15 Nov - 16 Nov
The Wheat House on Main (Unit 5)
Smart TV, books, printers
Timber Haven - Serene log home getaway with Wi-Fi, AC in NY Finger Lakes

Timber Haven - Serene log home getaway with Wi-Fi, AC in NY Finger Lakes

Cohocton
10.0 out of 10, Exceptional, (14)
"Beautiful, new, sparking clean log cabin home in a shady lot on a easy access country lane. Convenient quick access to scenic highway I-86, 390. Excellent high quality features and appliances throughout. Large spruce trees outside with bird feeders. Comfortable beds, easy climate control, convenient accessible washer/drier unit.Close enough (less than an hour) for a day trip to the fabulous town of Watkins Glen NY and State Park gorge are full of waterfalls."
United States
Sun B.
The price is HK$1,166
HK$1,497 total
includes taxes & fees
25 Nov - 26 Nov
Timber Haven - Serene log home getaway with Wi-Fi, AC in NY Finger Lakes
Fridge, microwave, oven, stovetop
Kellys Suite

Kellys Suite

Geneva
10.0 out of 10, Exceptional, (17)
"Wonderful apartment! Safe neighborhood and had a great stay, love the decorating!"
United States
Amanda G.
The price is HK$1,671
HK$2,662 total
includes taxes & fees
16 Nov - 17 Nov
Kellys Suite
Terrace/patio
Autumn Lake Escape - Cozy Fires, Sauna & Game Room

Autumn Lake Escape - Cozy Fires, Sauna & Game Room

2.0 star property
Hammondsport
10.0 out of 10, Exceptional, (1)
"We had an amazing time! The host was very communicative and helpful. The house was gorgeous inside and out. It was our first time at the finger lakes and we loved it. The area is amazing, we visited Watkins Glen and sampled a dozen wineries. All incredible. We will definitely be back. This house was absolutely perfect. "
United States
Emily H.
The price is HK$1,544
HK$3,871 total
includes taxes & fees
14 Dec - 15 Dec
Autumn Lake Escape - Cozy Fires, Sauna & Game Room
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.
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Top Middlesex Hotel Reviews

Hampton Inn Penn Yan

Hampton Inn Penn Yan

10/10 Excellent
"Great breakfast. Fun lounge with live music on the weekends. Helpful staff and easy check in and out. Plenty of safe parking. All around great stay!"
Joan 3-night trip
Posted 3 days ago
Hampton Inn Penn Yan

Find out more about Middlesex

Search for holiday rentals in Middlesex on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesex using one of the methods below:

  • View our selection of featured holiday rentals in Middlesex
  • Use the map to find apartments and other holiday homes in the Middlesex neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesex while they last

Look no further and take a look at our great range of rental properties in Middlesex!

Frequently asked questions

Are there holiday rentals in Middlesex?

Yes, there are holiday rentals close to the most popular sights in Middlesex, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middlesex has to offer?

Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!: This holiday home rental outside of Middlesex is located on a lake, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Middlesex?

Choose from 12 Expedia holiday rentals in Middlesex for a memorable holiday.

What can I see and do in Middlesex?

Canandaigua Lake and Clarks Gully are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find West River Marsh and Bristol Mountain Ski Resort.

What are holiday rentals like in Middlesex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlesex. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.