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

Middlesex Vacation Rentals

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Our top choices for Middlesex vacation rentals

1. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
The price is CA $106
CA $144 total
includes taxes & fees
Sep 9 - Sep 10
Beautiful Tiny home Near The Lake

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 CA $181
CA $363 total
includes taxes & fees
Sep 20 - Sep 21
Last Light Outdoor Retreat | the Lakehouse | On Seneca Wine Trail | Firepit

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

Beautiful Newly Renovated 1900s Farm House On 9 Acres
Rushville
The price is CA $174
CA $355 total
includes taxes & fees
Sep 9 - Sep 10
Beautiful Newly Renovated 1900s Farm House On 9 Acres

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

Last Light Outdoor Retreat | Wine Cellar | Seneca Wine Trail | Firepit
Lodi
The price is CA $181
CA $363 total
includes taxes & fees
Sep 20 - Sep 21
Last Light Outdoor Retreat | Wine Cellar | Seneca Wine Trail | Firepit

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 CA $186
CA $370 total
includes taxes & fees
Sep 20 - Sep 21
Last Light Outdoor Retreat | Cork Cottage | Seneca Wine Trail | Firepit

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 CA $185
CA $372 total
includes taxes & fees
Aug 26 - Aug 27
Last Light Outdoor Retreat | the Farmhouse | Seneca Wine Trail | Firepit

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

Last Light Outdoor Retreat | Wine Nook | Seneca Wine Trail | Firepit
Lodi
The price is CA $181
CA $367 total
includes taxes & fees
Aug 26 - Aug 27
Last Light Outdoor Retreat | Wine Nook | Seneca Wine Trail | Firepit

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

Last Light Outdoor Retreat | Seneca Modern | Seneca Wine Trail | Firepit
Lodi
The price is CA $241
CA $444 total
includes taxes & fees
Aug 30 - Aug 31
Last Light Outdoor Retreat | Seneca Modern | Seneca Wine Trail | Firepit

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 traveller
The price is CA $143
CA $298 total
includes taxes & fees
Sep 14 - Sep 15
Lovely 1 Bed Ranch Close to all Attractions

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 CA $162
CA $204 total
includes taxes & fees
Sep 3 - Sep 4
Ideal location for adventure all year round

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 CA $241
CA $339 total
includes taxes & fees
Aug 27 - Aug 28
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

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 CA $275
CA $385 total
includes taxes & fees
Aug 27 - Aug 28
Savannah Safari Tent & Breakfast-FLX Glamping

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 CA $111
CA $154 total
includes taxes & fees
Aug 29 - Aug 30
Sub Level Effiency

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 CA $201
CA $388 total
includes taxes & fees
Aug 27 - Aug 28
Modern Studio - Main St Penn Yan

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 CA $156
CA $327 total
includes taxes & fees
Sep 16 - Sep 17
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes

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 CA $117
CA $239 total
includes taxes & fees
Sep 21 - Sep 22
Finger Lakes Cottage

17. Private Backyard & Deck · Family-Friendly

Private Backyard & Deck · Family-Friendly
Penn Yan
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $365
CA $611 total
includes taxes & fees
Aug 27 - Aug 28
Private Backyard & Deck · Family-Friendly

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 CA $180
CA $232 total
includes taxes & fees
Sep 20 - Sep 21
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

19. Cozy Main St Studio - Penn Yan

Cozy Main St Studio - Penn Yan
Penn Yan
The price is CA $186
CA $371 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Main St Studio - Penn Yan

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 CA $266
CA $391 total
includes taxes & fees
Aug 31 - Sep 1
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

Find out more about Middlesex

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlesex. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.