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Holiday Homes in Middlesex

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Middlesex holiday homes

Coffee/tea maker, fridge, microwave, oven

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

Charming country ranch in the hills of the Finger Lakes
Naples
10.0 out of 10, Exceptional, (11 reviews)
"great location ... well kept surroundings.."
United States
James L.
The price is NZ$741
includes taxes & fees
15 Sept - 16 Sept
Charming country ranch in the hills of the Finger Lakes
Property grounds

2. Amazing Stargazing Retreat

Amazing Stargazing Retreat
Naples
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful home and property. Very clean, very quiet. The amenities were lovely and allowed for a restful getaway. Easy communication with host. Definitely recommend!"
United States
Becky H.
The price is NZ$780
includes taxes & fees
20 Sept - 21 Sept
Amazing Stargazing Retreat
Dining

3. Sub Level Effiency

Sub Level Effiency
Geneva
9.0 out of 10, Wonderful, (17 reviews)
"A great place to stay "
United States
Patrick
The price is NZ$204
includes taxes & fees
15 Sept - 16 Sept
Sub Level Effiency
Smart TV, books

4. Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain

Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
Naples
10.0 out of 10, Exceptional, (1 review)
The price is NZ$936
includes taxes & fees
14 Sept - 15 Sept
Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
TV

5. 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$900
includes taxes & fees
14 Oct - 15 Oct
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
Terrace/patio

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

‘The Gathering Place’: Rushville Home w/ Hot Tub
Rushville
9.6 out of 10, Exceptional, (14 reviews)
"Great stay with good location. "
United States
Emma R.
The price is NZ$1,140
includes taxes & fees
14 Sept - 15 Sept
‘The Gathering Place’: Rushville Home w/ Hot Tub
Terrace/patio

7. The Vita and Vine: Lakefront, Outdoor Theater

The Vita and Vine: Lakefront, Outdoor Theater
Rushville
The price is NZ$1,635
includes taxes & fees
14 Oct - 15 Oct
The Vita and Vine: Lakefront, Outdoor Theater
Property grounds

8. Fall Foliage/Parent's weekend/Pets Same day bookings accepted Terms apply

Fall Foliage/Parent's weekend/Pets Same day bookings accepted Terms apply
Canandaigua
8.8 out of 10, Excellent, (15 reviews)
"Nancy, the host did a great job of making sure I arrived ok and if I needed any information about the area. She was very knowledgeable about the Town of Canandaigua and the surrounding area."
United States
Charlie M.
The price is NZ$1,022
includes taxes & fees
14 Sept - 15 Sept
Fall Foliage/Parent's weekend/Pets Same day bookings accepted Terms apply
Coffee/tea maker, fridge, oven, stovetop

9. Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!

Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
Penn Yan
8.6 out of 10, Excellent, (9 reviews)
"Very peaceful 3 days. Amenities were as expected."
United States
alan
The price is NZ$422
includes taxes & fees
21 Sept - 22 Sept
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
Interior

10. 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 NZ$596
includes taxes & fees
15 Sept - 16 Sept
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
Coffee/tea maker, fridge, microwave, oven

11. 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, (87 reviews)
"This is the second time I’ve stayed here, great experience both times."
United States
Deanna S.
The price is NZ$527
includes taxes & fees
21 Sept - 22 Sept
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Exterior

12. PIne View Meadow

PIne View Meadow
Gorham
9.8 out of 10, Exceptional, (26 reviews)
"Property was great. 10/10 experience "
United States
Zach S.
The price is NZ$3,056
includes taxes & fees
16 Sept - 17 Sept
PIne View Meadow
Interior

13. 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$1,670
includes taxes & fees
27 Sept - 28 Sept
Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail
TV, DVD player

14. Chipmunk Cottage | Cozy Lakefront Escape

Chipmunk Cottage | Cozy Lakefront Escape
Penn Yan
10.0 out of 10, Exceptional, (1 review)
"Very clean,Very quaint. Great location for fishing and relaxing. Town's nearby to visit,and no external noise at cottage from neighbors and other rentals nearby."
United States
MaryLou S.
The price is NZ$789
includes taxes & fees
14 Sept - 15 Sept
Chipmunk Cottage | Cozy Lakefront Escape
Interior

15. Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, Exceptional, (29 reviews)
"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 NZ$398
includes taxes & fees
14 Sept - 15 Sept
Pet Friendly Keuka Yurt
Exterior

16. Lakeside Home - We accept direct same day bookings w VRBO booking;2 pets welcome

Lakeside Home - We accept direct same day bookings w VRBO booking;2 pets welcome
Canandaigua
8.0 out of 10, Very good, (4 reviews)
"Great peaceful location on Canandaigua Lake but close to town! Enjoyed relaxing on the dock!"
United States
Christopher H.
The price is NZ$1,408
includes taxes & fees
14 Sept - 15 Sept
Lakeside Home - We accept direct same day bookings w VRBO booking;2 pets welcome
TV

17. Beautiful Sunrise Views! Quiet Keuka Lake Escape

Beautiful Sunrise Views! Quiet Keuka Lake Escape
Penn Yan
10.0 out of 10, Exceptional, (1 review)
The price is NZ$1,131
includes taxes & fees
17 Sept - 18 Sept
Beautiful Sunrise Views! Quiet Keuka Lake Escape
Interior

18. Entire Home - 4 Bedroom - Sleeps 10 Canandaigua - Steps Off Main St / Downtown

Entire Home - 4 Bedroom - Sleeps 10 Canandaigua - Steps Off Main St / Downtown
Canandaigua
10.0 out of 10, Exceptional, (22 reviews)
"Great location!"
United States
Kelly D.
The price is NZ$940
includes taxes & fees
15 Sept - 16 Sept
Entire Home - 4 Bedroom - Sleeps 10 Canandaigua - Steps Off Main St / Downtown
Exterior

19. Wayfinder House | Game Room • Hot Tub • Movie Room

Wayfinder House | Game Room • Hot Tub • Movie Room
Canandaigua
The price is NZ$2,052
includes taxes & fees
22 Sept - 23 Sept
Wayfinder House | Game Room • Hot Tub • Movie Room
Coffee/tea maker, fridge, microwave, oven

20. Charming Farmhouse Retreat

Charming Farmhouse Retreat
Shortsville
10.0 out of 10, Exceptional, (21 reviews)
"We loved our time at the farmhouse, and wish we could have stayed longer. Check-in was easy, and communication with the owner was great. The house was clean, well-stocked, and very comfortable. Would definitely stay here again when we're in the area."
United States
Rich L.
The price is NZ$595
includes taxes & fees
14 Sept - 15 Sept
Charming Farmhouse Retreat
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

Showboat Hotel

Showboat Hotel

10/10 Excellent
"Perfect spot right on the lake. Rooms are modern and clean. Restaurant on the property has a nice selection of food and drinks. There was a band on Saturday that was a surprise! It was wonderful!!!"
Michaela 2-night trip
Posted less than an hour ago
Showboat Hotel

Find out more about Middlesex

Middlesex Holiday Homes information

Number of reviews
8,568
Accommodation
684 Holiday Homes
Lowest Price
NZ$152
Highest Price
NZ$454