Photo by Matthew Jay

Middlesex Holiday Rentals

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 prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Middlesex holiday rentals

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

Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva
Geneva
9.0 out of 10, Wonderful, (17)
"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$944
HK$1,473 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva
Fridge, microwave, oven, stovetop
Cozy 1BDR APT in Vibrant Downtown Geneva

Cozy 1BDR APT in Vibrant Downtown Geneva

Cozy 1BDR APT in Vibrant Downtown Geneva
Geneva
10.0 out of 10, Exceptional, (4)
"Didn’t get to vinyards, loved the accommodations though."
United Kingdom
laura r.
The price is HK$699
HK$1,786 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy 1BDR APT in Vibrant Downtown Geneva
Exterior
Pet Friendly Keuka Wagon

Pet Friendly Keuka Wagon

Pet Friendly Keuka Wagon
Penn Yan
9.6 out of 10, Exceptional, (25)
"Such an amazing, unique, peaceful and beautiful weekend getaway destination. "
United States
Ashley J.
The price is HK$816
HK$1,429 total
includes taxes & fees
4 Jan - 5 Jan 2026
Pet Friendly Keuka Wagon
Smart TV, books, printers
Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes

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

Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes
Cohocton
10.0 out of 10, Exceptional, (19)
"Great property with a wonderful host!!!!"
United States
Scott M.
The price is HK$1,119
HK$1,428 total
includes taxes & fees
3 Jan - 4 Jan 2026
Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes
1 bedroom, WiFi, bed sheets
Casita: Near Wineries & Keuka Lake: 100"Projector

Casita: Near Wineries & Keuka Lake: 100"Projector

Casita: Near Wineries & Keuka Lake: 100"Projector
Bath
9.8 out of 10, Exceptional, (7)
"This is a beautifully appointed tiny home, perfect for a quiet getaway! The decor is curated so tastefully, and the kitchen area equipped with stovetop and even olive oil and spices. The bed is comfortable and it was so nice to be able to bring our dog along. The hosts were lovely and provided quick and thoughtful communication. We enjoyed this quiet, lovely retreat, and it is close to wineries and not far from the Corning Museum of Glass, which we took the opportunity to visit. A great...
United States
Erika K.
The price is HK$1,154
HK$1,467 total
includes taxes & fees
12 Jan - 13 Jan 2026
Casita: Near Wineries & Keuka Lake: 100"Projector
Interior
Modern Studio APT in the Heart of Downtown Geneva

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)
"Highly recommend this place for your stay in the Finger Lakes! It was clean and comfy and easy walking distance to food and drink in Geneva. It was also conveniently located to many great wineries, breweries and other restaurants."
United States
Shelby L.
The price is HK$958
HK$2,132 total
includes taxes & fees
6 Jan - 7 Jan 2026
Modern Studio APT in the Heart of Downtown Geneva
Fridge, microwave, oven, stovetop
The Geneva Getaway- remodeled apartment walking distance from downtown Geneva

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, (31)
"Excellent place to stay. "
United States
April R.
The price is HK$630
HK$1,469 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Geneva Getaway- remodeled apartment walking distance from downtown Geneva
Exterior
Cozy little home located in the Finger Lakes

Cozy little home located in the Finger Lakes

Cozy little home located in the Finger Lakes
Dundee
10.0 out of 10, Exceptional, (2)
"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$778
HK$1,724 total
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy little home located in the Finger Lakes
Exterior detail
Spacious ‘GEM’ of the city

Spacious ‘GEM’ of the city

Spacious ‘GEM’ of the city
Geneva
9.8 out of 10, Exceptional, (44)
"Very clean, comfortable accommodations within walking distance of convenience stores, restaurants and shops. Very pretty area. "
United States
Anonymous traveller
The price is HK$1,322
HK$2,422 total
includes taxes & fees
7 Jan - 8 Jan 2026
Spacious ‘GEM’ of the city
Fridge, microwave, oven, stovetop
Kellys Suite

Kellys Suite

Kellys Suite
Geneva
10.0 out of 10, Exceptional, (21)
"Wonderful apartment! Safe neighborhood and had a great stay, love the decorating!"
United States
Amanda G.
The price is HK$1,671
HK$2,654 total
includes taxes & fees
4 Jan - 5 Jan 2026
Kellys Suite
Exterior
Top of the Fingerlakes, relaxing retreat.

Top of the Fingerlakes, relaxing retreat.

Top of the Fingerlakes, relaxing retreat.
Waterloo
9.8 out of 10, Exceptional, (28)
"Very comfortable, clean, and felt like home. Will be booking here again in June."
United States
April
The price is HK$902
HK$1,519 total
includes taxes & fees
5 Jan - 6 Jan 2026
Top of the Fingerlakes, relaxing retreat.
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!

The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Canandaigua
10.0 out of 10, Exceptional, (80)
"This is the second time I’ve stayed here, great experience both times."
United States
Deanna S.
The price is HK$1,399
HK$2,424 total
includes taxes & fees
31 Dec - 1 Jan 2026
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Outdoor dining
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!

1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!

1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!
3.0 star property
Penn Yan
9.8 out of 10, Exceptional, (81)
"Great location, water front property, close to wineries, dining and entertainment. "
United States
Jay M.
The price is HK$1,581
HK$2,772 total
includes taxes & fees
31 Dec - 1 Jan 2026
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!
Fridge, microwave, oven, stovetop
Peaceful, pet friendly and newly remodeled Geneva home

Peaceful, pet friendly and newly remodeled Geneva home

Peaceful, pet friendly and newly remodeled Geneva home
Geneva
9.8 out of 10, Exceptional, (26)
"Very comfortable and dog friendly which was great!"
United States
Matthew W.
The price is HK$1,360
HK$2,293 total
includes taxes & fees
7 Jan - 8 Jan 2026
Peaceful, pet friendly and newly remodeled Geneva home
Interior
Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, Exceptional, (28)
"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$816
HK$1,411 total
includes taxes & fees
2 Jan - 3 Jan 2026
Pet Friendly Keuka Yurt
Microwave, oven, stovetop, dishwasher
Lakeview and relax at the heart of Seneca lake

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, (10)
"This was a wonderful place. It was very clean and comfortable. We would definitely stay here again. "
United States
Rev John S.
The price is HK$2,246
HK$3,968 total
includes taxes & fees
31 Dec - 1 Jan 2026
Lakeview and relax at the heart of Seneca lake
Outdoor dining
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Rushville
9.0 out of 10, Wonderful, (4)
"We so much enjoyed our two night's stay at Rainey and Jeff's campground and can't wait to return. Upon arrival, Rainey showed us around the campground, led us to our adorably decorated yurt and invited us to join the campfire later that evening for gourmet smores. We opened a bottle of wine and sat on the egg swings for a while, enjoying the sound of the bullfrogs and the beautiful surroundings. Later we enjoyed sitting by the campfire talking with the other guests and Rainey and Jeff. After a...
United States
Stephanie M.
The price is HK$1,554
HK$2,159 total
includes taxes & fees
12 Jan - 13 Jan 2026
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Fridge, microwave, oven, stovetop
Chic Lakeview Getaway on Seneca Lake Wine Trail

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)
"Great location for visiting Watkins Glen, wineries and Keuka Lake area. Very clean and comfortable "
United States
Teresa R.
The price is HK$1,633
HK$3,394 total
includes taxes & fees
31 Dec - 1 Jan 2026
Chic Lakeview Getaway on Seneca Lake Wine Trail
Outdoor dining
Pet Friendly Log Cabin

Pet Friendly Log Cabin

Pet Friendly Log Cabin
Penn Yan
9.4 out of 10, Exceptional, (55)
"Very Clean, Peaceful and serene, enjoyed our time here. "
United States
Alisha W.
The price is HK$604
HK$1,191 total
includes taxes & fees
21 Jan - 22 Jan 2026
Pet Friendly Log Cabin
Fridge, microwave, oven, stovetop
Cottage with lake view at the heart of Seneca lake

Cottage with lake view at the heart of Seneca lake

Cottage with lake view at the heart of Seneca lake
Geneva
9.6 out of 10, Exceptional, (7)
"Wonderful place near Seneca Lake.Spacious with plenty of room for the 5 of us.Minutes from Geneva."
United States
Robert W.
The price is HK$2,021
HK$3,852 total
includes taxes & fees
31 Dec - 1 Jan 2026
Cottage with lake view at the heart of Seneca lake
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex Hotel Reviews

Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton

10/10 Excellent
"Yes"
Nicholas 2-night trip
Posted 21 hours ago
Hotel Canandaigua, Tapestry Collection by Hilton

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?

Keuka East: Spacious & Comfy: This holiday home rental outside of Middlesex is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 5 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 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.