A waterfall cascading through a narrow rock formation surrounded by greenery.

Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Middlesex vacation rentals

Living area

1. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
The price is ￥12,886
￥17,274 total
includes taxes & fees
Sep 2 - Sep 3
Beautiful Tiny home Near The Lake
Interior

2. Last Light Outdoor Retreat | the Lakehouse | On Seneca Wine Trail | Firepit

Last Light Outdoor Retreat | the Lakehouse | On Seneca Wine Trail | Firepit
Lodi
The price is ￥21,530
￥43,514 total
includes taxes & fees
Aug 31 - Sep 1
Last Light Outdoor Retreat | the Lakehouse | On Seneca Wine Trail | Firepit
Living area

3. Beautiful Newly Renovated 1900s Farm House On 9 Acres

Beautiful Newly Renovated 1900s Farm House On 9 Acres
Rushville
The price is ￥18,626
￥39,226 total
includes taxes & fees
Sep 9 - Sep 10
Beautiful Newly Renovated 1900s Farm House On 9 Acres
Property grounds

4. Last Light Outdoor Retreat | Wine Cellar | Seneca Wine Trail | Firepit

Last Light Outdoor Retreat | Wine Cellar | Seneca Wine Trail | Firepit
Lodi
Last Light Outdoor Retreat | Wine Cellar | Seneca Wine Trail | Firepit
Interior

5. Last Light Outdoor Retreat | Cork Cottage | Seneca Wine Trail | Firepit

Last Light Outdoor Retreat | Cork Cottage | Seneca Wine Trail | Firepit
Lodi
The price is ￥21,664
￥43,484 total
includes taxes & fees
Sep 20 - Sep 21
Last Light Outdoor Retreat | Cork Cottage | Seneca Wine Trail | Firepit
Room

6. Last Light Outdoor Retreat | the Farmhouse | Seneca Wine Trail | Firepit

Last Light Outdoor Retreat | the Farmhouse | Seneca Wine Trail | Firepit
Lodi
The price is ￥22,065
￥44,283 total
includes taxes & fees
Aug 31 - Sep 1
Last Light Outdoor Retreat | the Farmhouse | Seneca Wine Trail | Firepit
Room

7. Last Light Outdoor Retreat | Wine Nook | Seneca Wine Trail | Firepit

Last Light Outdoor Retreat | Wine Nook | Seneca Wine Trail | Firepit
Lodi
Last Light Outdoor Retreat | Wine Nook | Seneca Wine Trail | Firepit
Interior

8. Last Light Outdoor Retreat | Seneca Modern | Seneca Wine Trail | Firepit

Last Light Outdoor Retreat | Seneca Modern | Seneca Wine Trail | Firepit
Lodi
Last Light Outdoor Retreat | Seneca Modern | Seneca Wine Trail | Firepit
Private kitchen

9. Lovely 1 Bed Ranch Close to all Attractions

Lovely 1 Bed Ranch Close to all Attractions
Canandaigua NY
4.0 out of 10, (1 review)
"There is NO house number on the building. The host did NOT provide us with info prior to arrival, we had to message him to get access. It appeared that check in was at 4:00, but turned out it was 3:00. The actual property appearance does NOT look like the pictures online. Outside is overgrown, dirty and cobweb’s everywhere. Inside smells musty and gross. Flies everywhere, spiders in the bathroom and shower. It was not clean under the bed. There’s no bathroom soaps or wash clothes and the towels...
United States
Anonymous traveler
The price is ￥17,194
￥35,769 total
includes taxes & fees
Sep 7 - Sep 8
Lovely 1 Bed Ranch Close to all Attractions
Living area

10. Ideal location for adventure all year round

Ideal location for adventure all year round
Naples
10.0 out of 10, Exceptional, (7 reviews)
"house was clean, quiet area, perfect for my one night stay for a wedding"
United States
Alexis M.
The price is ￥18,626
￥23,447 total
includes taxes & fees
Sep 3 - Sep 4
Ideal location for adventure all year round
Interior

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

Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Rushville
9.2 out of 10, Wonderful, (5 reviews)
"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 ￥27,841
￥38,309 total
includes taxes & fees
Aug 27 - Aug 28
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Property grounds

12. Savannah Safari Tent & Breakfast-FLX Glamping

Savannah Safari Tent & Breakfast-FLX Glamping
Rushville
10.0 out of 10, Exceptional, (10 reviews)
"Great location, amazing hosts, wonderful morning breakfasts and coffee served! Good relaxation experience, swimming pond was awesome, going back next summer!"
United States
Faithann B.
The price is ￥31,818
￥44,902 total
includes taxes & fees
Aug 27 - Aug 28
Savannah Safari Tent & Breakfast-FLX Glamping
Dining

13. Sub Level Effiency

Sub Level Effiency
Geneva
8.8 out of 10, Excellent, (16 reviews)
"A great place to stay "
United States
Patrick
The price is ￥12,886
￥17,756 total
includes taxes & fees
Aug 29 - Aug 30
Sub Level Effiency
Interior

14. Modern Studio - Main St Penn Yan

Modern Studio - Main St Penn Yan
Penn Yan
9.6 out of 10, Exceptional, (15 reviews)
"My girlfriend and i went on our first trip together here. It was very cozy! Was walking distance to all the things we wanted to do. We were planning another trip before the weekend was even over. "
United States
Kevin G.
The price is ￥23,195
￥45,162 total
includes taxes & fees
Aug 27 - Aug 28
Modern Studio - Main St Penn Yan
Interior

15. Cozy tiny home with Sunrise Views in the Heart of Finger Lakes

Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
Penn Yan
The price is ￥18,041
￥37,670 total
includes taxes & fees
Sep 16 - Sep 17
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
Living area

16. Finger Lakes Cottage

Finger Lakes Cottage
Prattsburgh
9.8 out of 10, Exceptional, (102 reviews)
"Cute place!"
United States
Jessica W.
The price is ￥13,523
￥27,618 total
includes taxes & fees
Sep 24 - Sep 25
Finger Lakes Cottage
Room

17. Private Backyard & Deck · Family-Friendly

Private Backyard & Deck · Family-Friendly
Penn Yan
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥42,268
￥71,055 total
includes taxes & fees
Aug 27 - Aug 28
Private Backyard & Deck · Family-Friendly
Pool

18. Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
Penn Yan
9.8 out of 10, Exceptional, (161 reviews)
"The cabin and property was perfect for us, the only negative was a lack of water pressure using the shower."
United States
Jeffrey
The price is ￥23,068
￥29,400 total
includes taxes & fees
Sep 23 - Sep 24
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
Room

19. Cozy Main St Studio - Penn Yan

Cozy Main St Studio - Penn Yan
Penn Yan
The price is ￥21,477
￥43,444 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Main St Studio - Penn Yan
Exterior

20. Sunny Trails Getaway Cabin

Sunny Trails Getaway Cabin
Cohocton
10.0 out of 10, Exceptional, (17 reviews)
"Very peaceful and relaxing place"
United States
Orlando
The price is ￥30,784
￥45,525 total
includes taxes & fees
Aug 30 - Aug 31
Sunny Trails Getaway Cabin
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

8/10 Good
"Breakfast cafe area was clean and well stocked. That being said, the coffee maker was not completely in working order and the ice machine on our floor was inoperable as well. Those were the only issues. Other than that our stay was good. The staff were friendly and helpful."
Ray 3-night trip
Posted less than an hour 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 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 in the heart of FLX wine country! ALL are welcome!: 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.

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.