Photo by Matthew Jay

Middlesex Vacation Rentals

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Middlesex

Cozy Cabin With 165 Ft Beach and wood-fired hot tub! Center of FLX wine country!

10.0 out of 10, Exceptional, (247)
"Cabin was clean and comfortable. The kitchen was well stocked. The view from the living room was gorgeous. We enjoyed the lovely private dock and the view from the firepit. It was a serene setting."
The price is ¥46,954
¥78,470 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Cabin With 165 Ft Beach and wood-fired hot tub! Center of FLX wine country!

Family fun, wine tours and beautiful sunsets

9.8 out of 10, Exceptional, (169)
"Nice house with great views of the lake and easy access to kayaks/lifejackets etc. "
Family fun, wine tours and beautiful sunsets

Lakeside Home, New Pool, Carriage House, level & private, 6 BR, 120' frontage!

10.0 out of 10, Exceptional, (114)
"This property was great!"
Lakeside Home, New Pool, Carriage House, level & private, 6 BR, 120' frontage!

Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK

9.2 out of 10, Wonderful, (306)
"We were sad to leave. Quiet, clean, cozy little stay. "
Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK

Pine Grove Cabin

8.8 out of 10, Excellent, (6)
"We just needed a place without light pollution near Lincoln hill farm, so we could go to a concert, then lay in the grass and see some meteors. Pretty great."
The price is ¥10,452
¥23,230 total
includes taxes & fees
Oct 5 - Oct 6
Pine Grove Cabin

THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!

9.8 out of 10, Exceptional, (59)
"The place was great, just outside of town but nice and private. They had everything we needed and the view was beautiful! "
THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!

Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!

9.6 out of 10, Exceptional, (64)
"We stayed here for my sister’s bachelorette weekend and loved every second of it! The house is perfect for a big group. Only con was no mirrors in a lot of the bedrooms. "
Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!

WELCOME! WE ARE PET FRIENDLY.

9.8 out of 10, Exceptional, (293)
"Beautiful place"
WELCOME! WE ARE PET FRIENDLY.

Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..

8.6 out of 10, Excellent, (222)
"Very private, quiet getaway! The cottage was very cute tucked away in the woods. It was very peaceful."
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..

Keuka East: Spacious & Comfy

9.6 out of 10, Exceptional, (144)
"We had a fantastic stay. It was the perfect place for our group. The house had everything we needed. The location was great for touring around the Finger Lakes. "
Keuka East: Spacious & Comfy

The Flatts at North Shore

3.5 star property
9.8 out of 10, Exceptional, (93)
"Large nicely appointed condo. Bed was comfortable. Very nice bathrooms. Appreciated washer, dryer and dishwasher. Close to lake and many restaurants. "
The Flatts at North Shore

Canadaigua Lake Sunset Oasis: Private Beach, Family Fun Wineries, CMAC, Shopping

10.0 out of 10, Exceptional, (15)
"Great location"
The price is ¥56,963
¥123,262 total
includes taxes & fees
Oct 6 - Oct 7
Canadaigua Lake Sunset Oasis: Private Beach, Family Fun Wineries, CMAC, Shopping

Cozy new England style cottage Right on Wine and Beer Trail

9.8 out of 10, Exceptional, (273)
"We had an amazing time and are already planning a trip back. "
Cozy new England style cottage Right on Wine and Beer Trail

On-the-Water Romantic Cabin Breathtaking View Beach Fire Pit! Oct-Nov Availabity

9.2 out of 10, Wonderful, (185)
"We enjoyed ourselves at this lakefront location. It was also great to have a great view of the Garrett Chapel. We also used Reagan Rentals for a kayak. Great trip! "
On-the-Water Romantic Cabin Breathtaking View Beach Fire Pit! Oct-Nov Availabity

FROG HOUSE - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! 4 Seasons

2.0 star property
10.0 out of 10, Exceptional, (11)
"Overall, our impression is that the property was very comfortable as a campsite. The property was very much what we had hoped for -- (mostly) quiet, forest, trails. Thought "Frog House" meant frog sounds all night, but .... "
FROG HOUSE - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! 4 Seasons

LakeSide Escape on Canandaigua Lake : Finger Lakes

9.6 out of 10, Exceptional, (46)
"Perfect place for us to stay. The dock was beautiful!"
LakeSide Escape on Canandaigua Lake : Finger Lakes

Camp Believe It is a secluded cabin with 50 acres of hiking trails!

10.0 out of 10, Exceptional, (8)
"This cabin was perfect! We got in late but there are motion sensor lights outside and the inside was lit up as well. It was clean, stocked, comfortable and really made our trip even more enjoyable. Great place to stay!!"
The price is ¥20,607
¥29,179 total
includes taxes & fees
Oct 5 - Oct 6
Camp Believe It is a secluded cabin with 50 acres of hiking trails!

Wildflower-Seneca Lake-Water View-Hot Tub-Wine Trail - Pets, Steps to Lake-Acre of Privacy

8.6 out of 10, Excellent, (101)
"The cleanliness seemed fine but the structure of trailer seemed to have signs of damage in the past,no lights around hot tub,couldn’t see steps getting out of it,,,and although it was unusually hot there was no coolness in living room and middle bedroom,and I would also suggest an up to date toaster, bagels had to be pried out of it and had to eat burnt,all in all the host was very easy to communicate wth, any questions were answered quickly and to the point"
Wildflower-Seneca Lake-Water View-Hot Tub-Wine Trail - Pets, Steps to Lake-Acre of Privacy

Lakeaholic Living On Canandaigua Lake

10.0 out of 10, Exceptional, (84)
"The house is modern and very clean with a basement game room, hangout space, main floor kitchen with two separate living rooms that allows different activities to be enjoyed. The viwes are wonderful from the deck that has a motorized retractable awning. Would book this again!!"
Lakeaholic Living On Canandaigua Lake

Welcome to Camp Waneta.

9.6 out of 10, Exceptional, (18)
"The house is tiny but nicely designed and built. It has all the necessities, a fire pit, a grill (outdoor) and direct access to a private dock where you can enjoy the lake view and fishing. We are also glad to know we are the first guests so everything is brand new. We enjoyed our stay. My kids love the fire pit, grill, house etc. My husband loves the fishing. By the way, it’s easy to fish; we caught 8 fish in about half hours. The house is close to a lot of attractions, e.g. finger lake area,...
The price is ¥15,877
¥33,853 total
includes taxes & fees
Oct 19 - Oct 20
Welcome to Camp Waneta.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middlesex Hotel Reviews

Find out more about Middlesex

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 vacation rentals in Middlesex?

Yes, we offer vacation rentals near popular attractions in Middlesex, or you can go with a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Middlesex?

Cozy Cabin With 165 Ft Beach and wood-fired hot tub! Center of FLX wine country!: This vacation home rental outside of Middlesex is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals will I find in Middlesex?

Choose from 11 Expedia vacation rentals in Middlesex for a memorable vacation.

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 larger area, you’ll find West River Marsh and Bristol Mountain Ski Resort.

What are vacation rentals like in Middlesex?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Middlesex. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip.