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

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Middlesex holiday homes

A hot tub on a wooden deck with a clear sky and trees in the background.

1. Amazing Stargazing Retreat

Amazing Stargazing Retreat
Naples
9.6 out of 10, 5, (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 £312
includes taxes & fees
17 Sept - 18 Sept
Amazing Stargazing Retreat
A modern kitchen with a central island, wooden chairs, and green cabinetry.

2. 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, 11, (11 reviews)
"great location ... well kept surroundings.."
United States
James L.
The price is £315
includes taxes & fees
15 Sept - 16 Sept
Charming country ranch in the hills of the Finger Lakes
A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

3. Sub Level Effiency

Sub Level Effiency
Geneva
9.0 out of 10, 17, (17 reviews)
"A great place to stay "
United States
Patrick
The price is £91
includes taxes & fees
15 Sept - 16 Sept
Sub Level Effiency
A house with a patio area featuring a fire pit, outdoor furniture, and a covered deck with an umbrella.

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

‘The Gathering Place’: Rushville Home w/ Hot Tub
Rushville
9.6 out of 10, 14, (14 reviews)
"Great stay with good location. "
United States
Emma R.
The price is £493
includes taxes & fees
16 Sept - 17 Sept
‘The Gathering Place’: Rushville Home w/ Hot Tub
A spacious living room with a grey sectional sofa, a wooden coffee table, and a kitchen in the background.

5. 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, 1, (1 review)
The price is £394
includes taxes & fees
15 Sept - 16 Sept
Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
A yurt interior with a round ceiling, a mounted television, a wooden barrel, and a small kitchenette.

6. Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, 29, (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 £175
includes taxes & fees
15 Sept - 16 Sept
Pet Friendly Keuka Yurt
A spacious living room with a large window, a ceiling fan, and a flat-screen TV.

7. 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, 5, (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 £400
includes taxes & fees
14 Oct - 15 Oct
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
A two-story house with a driveway and landscaped yard.

8. PIne View Meadow

PIne View Meadow
Gorham
9.8 out of 10, 26, (26 reviews)
"Property was great. 10/10 experience "
United States
Zach S.
The price is £1,339
includes taxes & fees
21 Sept - 22 Sept
PIne View Meadow
A wooden cabin interior with a TV, sofa, and a view of a lake.

9. Chipmunk Cottage | Cozy Lakefront Escape

Chipmunk Cottage | Cozy Lakefront Escape
Penn Yan
10.0 out of 10, 1, (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 £341
includes taxes & fees
28 Sept - 29 Sept
Chipmunk Cottage | Cozy Lakefront Escape
A house with a deck, outdoor seating, and a dock over water.

10. The Vita and Vine: Lakefront, Outdoor Theater

The Vita and Vine: Lakefront, Outdoor Theater
Rushville
The price is £673
includes taxes & fees
13 Oct - 14 Oct
The Vita and Vine: Lakefront, Outdoor Theater
A wooden dock extending into a body of water, with a building and greenery in the background.

11. 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, 15, (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 £447
includes taxes & fees
15 Sept - 16 Sept
Fall Foliage/Parent's weekend/Pets Same day bookings accepted Terms apply
A kitchen with wooden cabinets, a microwave, and a dining table with woven placemats.

12. 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, 87, (87 reviews)
"This is the second time I’ve stayed here, great experience both times."
United States
Deanna S.
The price is £229
includes taxes & fees
15 Sept - 16 Sept
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
A spacious room with wooden flooring, wicker furniture, and large windows allowing natural light.

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 £627
includes taxes & fees
22 Sept - 23 Sept
Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail
A modern kitchen with a large island, a sink, and a window overlooking a yard.

14. 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, 9, (9 reviews)
"Very peaceful 3 days. Amenities were as expected."
United States
alan
The price is £162
includes taxes & fees
21 Sept - 22 Sept
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
A compact kitchen with a sink, stove, and wooden cabinets.

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 £262
includes taxes & fees
15 Sept - 16 Sept
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
A waterfront property with a dock, a house with a deck, and a large tree.

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, 4, (4 reviews)
"Great peaceful location on Canandaigua Lake but close to town! Enjoyed relaxing on the dock!"
United States
Christopher H.
The price is £617
includes taxes & fees
15 Sept - 16 Sept
Lakeside Home - We accept direct same day bookings w VRBO booking;2 pets welcome
A modern kitchen with white cabinets, a black refrigerator, and a wooden floor.

17. Charming Farmhouse Retreat

Charming Farmhouse Retreat
Shortsville
10.0 out of 10, 21, (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 £265
includes taxes & fees
15 Sept - 16 Sept
Charming Farmhouse Retreat

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, 22, (22 reviews)
"Great location!"
United States
Kelly D.
The price is £412
includes taxes & fees
15 Sept - 16 Sept
Entire Home - 4 Bedroom - Sleeps 10 Canandaigua - Steps Off Main St / Downtown
A large, multi-story house with a well-maintained lawn and a circular driveway.

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

Wayfinder House | Game Room • Hot Tub • Movie Room
Canandaigua
The price is £895
includes taxes & fees
22 Sept - 23 Sept
Wayfinder House | Game Room • Hot Tub • Movie Room
A lakeside deck with picnic tables, a wooden dock, and boats.

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

Canadaigua Lake Sunset Oasis: Private Beach, Family Fun Wineries, CMAC, Shopping
Canandaigua
10.0 out of 10, 19, (19 reviews)
"Gorgeous view. Comfortable beds. Great stay "
United States
Sara L.
The price is £714
includes taxes & fees
13 Oct - 14 Oct
Canadaigua Lake Sunset Oasis: Private Beach, Family Fun Wineries, CMAC, Shopping
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

Comfort Inn & Suites Farmington - Victor

Comfort Inn & Suites Farmington - Victor

8/10 Good
"Hotel was fine for an overnight stay. Meets expectations"
Melissa 1-night trip
Posted 12 hours ago
Comfort Inn & Suites Farmington - Victor

Find out more about Middlesex

Middlesex Holiday Homes information

Number of reviews
285
Accommodation
686 Holiday Homes
Lowest Price
£91
Highest Price
£1,339