Middlesex Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Middlesex holiday rentals

1 bedroom, WiFi, bed sheets

Pet Friendly Keuka Wagon

Pet Friendly Keuka Wagon
Penn Yan
9.6 out of 10, Exceptional, (25 reviews)
"Such an amazing, unique, peaceful and beautiful weekend getaway destination. "
United States
Ashley J.
The price is HK$813
HK$1,378 total
includes taxes & fees
9 Mar - 10 Mar
Pet Friendly Keuka Wagon
Property grounds

Top of the Fingerlakes, relaxing retreat.

Top of the Fingerlakes, relaxing retreat.
Waterloo
9.8 out of 10, Exceptional, (29 reviews)
"Great place to stay. "
United States
Jose
The price is HK$809
HK$1,427 total
includes taxes & fees
17 Feb - 18 Feb
Top of the Fingerlakes, relaxing retreat.
Smart TV

❤ of Seneca Wine Trail☞A/C☞Fire Pit☞Smart TV

❤ of Seneca Wine Trail☞A/C☞Fire Pit☞Smart TV
Geneva
9.8 out of 10, Exceptional, (42 reviews)
"Cabin was nice. Got married that Saturday so used for bride and bridesmaids to get ready. Was a little cramped for 7 people but for two to four people would be perfect."
United States
Sharon D.
The price is HK$1,165
HK$3,311 total
includes taxes & fees
15 Feb - 16 Feb
❤ of Seneca Wine Trail☞A/C☞Fire Pit☞Smart TV
Smart TV

Cozy 1BDR APT in Vibrant Downtown Geneva

Cozy 1BDR APT in Vibrant Downtown Geneva
Geneva
10.0 out of 10, Exceptional, (4 reviews)
"The apartment was adorable. Perfect place to stay for our needs. Ryan was great and very responsive to my emails. Would definitely stay here again!"
United States
Stacey L.
The price is HK$703
HK$1,805 total
includes taxes & fees
15 Feb - 16 Feb
Cozy 1BDR APT in Vibrant Downtown Geneva
Interior

Beautiful Keuka Lake Home close to Penn Yan

Beautiful Keuka Lake Home close to Penn Yan
Penn Yan
10.0 out of 10, Exceptional, (7 reviews)
"This property was beautiful and in a great location. Good for a family!"
United States
Ashley E.
The price is HK$703
HK$2,005 total
includes taxes & fees
22 Feb - 23 Feb
Beautiful Keuka Lake Home close to Penn Yan
Outdoor dining

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 reviews)
"The space was very clean and provided nice proximity to the lake and things to do in the area. It was a great stay!"
United States
Kaitlyn D.
The price is HK$950
HK$1,481 total
includes taxes & fees
17 Feb - 18 Feb
Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva
Interior

Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, Exceptional, (28 reviews)
"Very pet friendly, great location to many local wineries. Will definitely stay here again. For a longer time."
United States
Ian B.
The price is HK$821
HK$1,387 total
includes taxes & fees
16 Feb - 17 Feb
Pet Friendly Keuka Yurt
Exterior

Pet Friendly Log Cabin

Pet Friendly Log Cabin
Penn Yan
9.4 out of 10, Exceptional, (56 reviews)
"Very Clean, Peaceful and serene, enjoyed our time here. "
United States
Alisha W.
The price is HK$812
HK$1,378 total
includes taxes & fees
17 Feb - 18 Feb
Pet Friendly Log Cabin
Smart TV, fireplace

Hubbs Cellar at JS Hubbs Guest House

Hubbs Cellar at JS Hubbs Guest House
Hammondsport
10.0 out of 10, Exceptional, (7 reviews)
"Clean, modern, great host, and walking distance to a beautiful water view. So nice!"
United States
Jonathan S.
The price is HK$645
HK$2,018 total
includes taxes & fees
25 Feb - 26 Feb
Hubbs Cellar at JS Hubbs Guest House
Dining

Sub Level Effiency

Sub Level Effiency
Geneva
7.8 out of 10, Good, (7 reviews)
"A great place to stay "
United States
Patrick
The price is HK$563
HK$795 total
includes taxes & fees
1 Mar - 2 Mar
Sub Level Effiency
2 bedrooms, WiFi, bed sheets

The Johnson Chalet in Bristol/Canandaigua*HOT TUB*

The Johnson Chalet in Bristol/Canandaigua*HOT TUB*
Canandaigua
10.0 out of 10, Exceptional, (5 reviews)
"Our stay was relaxing and very comfortable. The cottage is well appointed and upscale in its feel. And it's located in a verybprivate setting while still being close to major roads. We enjoyed our stay."
United States
Kip B.
The price is HK$1,633
HK$3,113 total
includes taxes & fees
17 Feb - 18 Feb
The Johnson Chalet in Bristol/Canandaigua*HOT TUB*
1 bedroom, WiFi, bed sheets

Casita: Near Wineries & Keuka Lake: 100"Projector

Casita: Near Wineries & Keuka Lake: 100"Projector
Bath
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful tiny house, it has everything you could need. Great location, very quiet and clean. We could only recommend going there, we loved it! "
United States
Manon R.
The price is HK$1,290
HK$1,619 total
includes taxes & fees
1 Mar - 2 Mar
Casita: Near Wineries & Keuka Lake: 100"Projector
Exterior

Timber Haven - Serene year-round log home getaway with Wi-Fi, HVAC

Timber Haven - Serene year-round log home getaway with Wi-Fi, HVAC
Cohocton
10.0 out of 10, Exceptional, (25 reviews)
"Loved the cabin We had a great stay"
United States
Sue T.
The price is HK$1,063
HK$1,366 total
includes taxes & fees
17 Feb - 18 Feb
Timber Haven - Serene year-round log home getaway with Wi-Fi, HVAC
Exterior detail

Spacious ‘GEM’ of the city

Spacious ‘GEM’ of the city
Geneva
9.8 out of 10, Exceptional, (44 reviews)
"Very clean, comfortable accommodations within walking distance of convenience stores, restaurants and shops. Very pretty area. "
United States
Anonymous traveller
The price is HK$1,329
HK$2,565 total
includes taxes & fees
17 Feb - 18 Feb
Spacious ‘GEM’ of the city
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, (11 reviews)
"Beautiful apartment, very clean. Great location-walking distances to restaurants and shops"
United States
Brooke E.
The price is HK$963
HK$2,127 total
includes taxes & fees
25 Feb - 26 Feb
Modern Studio APT in the Heart of Downtown Geneva
Outdoor dining

Cozy little home located in the Finger Lakes

Cozy little home located in the Finger Lakes
Dundee
10.0 out of 10, Exceptional, (2 reviews)
"We only used the property to sleep in while visiting family locally. It was very clean and had basics."
United States
Heather Z.
The price is HK$1,028
HK$1,983 total
includes taxes & fees
10 Mar - 11 Mar
Cozy little home located in the Finger Lakes
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, (80 reviews)
"This is the second time I’ve stayed here, great experience both times."
United States
Deanna S.
The price is HK$1,407
HK$2,420 total
includes taxes & fees
25 Feb - 26 Feb
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Smart TV, fireplace

Charming Farmhouse Retreat

Charming Farmhouse Retreat
Shortsville
10.0 out of 10, Exceptional, (16 reviews)
"Peaceful!!!"
United States
Kevin D.
The price is HK$1,001
HK$2,460 total
includes taxes & fees
17 Feb - 18 Feb
Charming Farmhouse Retreat
Fridge, microwave, oven, stovetop

Stunning Little House Near Canandagiua Lake

Stunning Little House Near Canandagiua Lake
Canandaigua
The price is HK$383
HK$981 total
includes taxes & fees
16 Feb - 17 Feb
Stunning Little House Near Canandagiua Lake
Interior

The Nautilus at JS Hubbs Guest House

The Nautilus at JS Hubbs Guest House
Hammondsport
10.0 out of 10, Exceptional, (4 reviews)
"Walter was fantastic! We had a wonderful stay and will be back!!"
United States
Katherine F.
The price is HK$1,290
HK$2,854 total
includes taxes & fees
25 Feb - 26 Feb
The Nautilus at JS Hubbs Guest House
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

Microtel by Wyndham Penn Yan Finger Lakes Region

Microtel by Wyndham Penn Yan Finger Lakes Region

10/10 Excellent
"Last minute stay. Room very clean and staff friendly."
Joy 1-night trip
Posted 5 days ago
Microtel by Wyndham Penn Yan Finger Lakes Region

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
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  • 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?

Lakeaholic Living On Canandaigua Lake: This holiday home rental outside of Middlesex is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Middlesex?

Choose from 13 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.