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

Middlesex Holiday Rentals

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Our top choices for Middlesex holiday rentals

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

Last Light Outdoor Retreat | the Farmhouse | Seneca Wine Trail | Firepit
Lodi
Last Light Outdoor Retreat | the Farmhouse | Seneca Wine Trail | Firepit

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

Beautiful Newly Renovated 1900s Farm House On 9 Acres
Rushville
The price is NZ$460
includes taxes & fees
16 Aug - 17 Aug
Beautiful Newly Renovated 1900s Farm House On 9 Acres

3. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
The price is NZ$273
includes taxes & fees
9 Sept - 10 Sept
Beautiful Tiny home Near The Lake

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

Last Light Outdoor Retreat | Seneca Modern | Seneca Wine Trail | Firepit
Lodi
The price is NZ$577
includes taxes & fees
17 Aug - 18 Aug
Last Light Outdoor Retreat | Seneca Modern | Seneca Wine Trail | Firepit

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

Last Light Outdoor Retreat | Wine Nook | Seneca Wine Trail | Firepit
Lodi
The price is NZ$555
includes taxes & fees
17 Aug - 18 Aug
Last Light Outdoor Retreat | Wine Nook | Seneca Wine Trail | Firepit

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

Last Light Outdoor Retreat | Cork Cottage | Seneca Wine Trail | Firepit
Lodi
The price is NZ$564
includes taxes & fees
17 Aug - 18 Aug
Last Light Outdoor Retreat | Cork Cottage | Seneca Wine Trail | Firepit

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

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

8. 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 NZ$372
includes taxes & fees
9 Sept - 10 Sept
Lovely 1 Bed Ranch Close to all Attractions

9. PIne View Meadow

PIne View Meadow
Gorham
9.6 out of 10, Exceptional, (25 reviews)
"We had a wonderful stay! The house was spotless and had plenty of space for everyone to relax comfortably. We were lucky enough to get snow while we were there, which made everything feel extra magical. The host even provided sleds so our kids could slide down the hill & it truly felt like a winter wonderland.The hosts were extremely responsive and went above and beyond to accommodate us, especially with some weather related travel issues while we were flying in. We couldn’t say enough good...
United States
Brandy N.
The price is NZ$3,056
includes taxes & fees
8 Sept - 9 Sept
PIne View Meadow

10. That Cottage by the Lake!!

That Cottage by the Lake!!
Canandaigua
9.8 out of 10, Exceptional, (19 reviews)
"Cute little cottage, just a short walk down to the lake."
United States
Rebecca P.
The price is NZ$739
includes taxes & fees
16 Aug - 17 Aug
That Cottage by the Lake!!

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 NZ$419
includes taxes & fees
15 Aug - 16 Aug
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 NZ$476
includes taxes & fees
15 Aug - 16 Aug
Savannah Safari Tent & Breakfast-FLX Glamping

13. The Gathering Place: Rushville Home w/ Hot Tub

The Gathering Place: Rushville Home w/ Hot Tub
3.0 star property
Rushville
The price is NZ$1,093
includes taxes & fees
18 Aug - 19 Aug
The Gathering Place: Rushville Home w/ Hot Tub

14. Charming country ranch in the hills of the Finger Lakes

Charming country ranch in the hills of the Finger Lakes
Naples
9.8 out of 10, Exceptional, (10 reviews)
"great location ... well kept surroundings.."
United States
James L.
The price is NZ$728
includes taxes & fees
24 Aug - 25 Aug
Charming country ranch in the hills of the Finger Lakes

15. ‘The Gathering Place’: Rushville Home w/ Hot Tub

‘The Gathering Place’: Rushville Home w/ Hot Tub
Rushville
9.4 out of 10, Exceptional, (12 reviews)
"Great stay with good location. "
United States
Emma R.
The price is NZ$1,122
includes taxes & fees
18 Aug - 19 Aug
‘The Gathering Place’: Rushville Home w/ Hot Tub

16. Private Backyard & Deck · Family-Friendly

Private Backyard & Deck · Family-Friendly
Penn Yan
10.0 out of 10, Exceptional, (3 reviews)
"Great house. It was perfect for us. Clean, beds were comfy and location was quiet and beautiful."
United States
Emily W.
The price is NZ$758
includes taxes & fees
17 Aug - 18 Aug
Private Backyard & Deck · Family-Friendly

17. Backyard Fire Ring & Deck w/ Grill · Games

Backyard Fire Ring & Deck w/ Grill · Games
Stanley
9.6 out of 10, Exceptional, (21 reviews)
"Good property overall"
United States
Daveon W.
The price is NZ$754
includes taxes & fees
19 Aug - 20 Aug
Backyard Fire Ring & Deck w/ Grill · Games

18. Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail

Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail
Naples
The price is NZ$1,794
includes taxes & fees
8 Sept - 9 Sept
Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail

19. Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook

Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
Canandaigua
8.0 out of 10, Very good, (5 reviews)
"Our stay worked out really well for us. Nice view of the lake. The deck actually has a covered gazebo! "
United States
Corey P.
The price is NZ$1,049
includes taxes & fees
14 Sept - 15 Sept
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook

20. Ideal location for adventure all year round

Ideal location for adventure all year round
Naples
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and accommodating. Would stay again!!"
United States
Susan W.
The price is NZ$251
includes taxes & fees
16 Aug - 17 Aug
Ideal location for adventure all year round
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middlesex holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middlesex. 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 Middlesex. 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 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 holiday 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 Middlesex short-term rentals, that won’t be hard to do.

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?

Cozy Cabin With 165 Ft Beach in the heart of FLX wine country! ALL are welcome!: This holiday home rental outside of Middlesex is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Middlesex?

Choose from 11 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.