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

Holiday Homes in Middlesex

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Middlesex holiday homes

A modern kitchen with a central island, wooden chairs, and green cabinetry.

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 €368
includes taxes & fees
8 Sept - 9 Sept
Charming country ranch in the hills of the Finger Lakes
A spacious living room with a large window, a ceiling fan, and a flat-screen TV.

2. 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.
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
A house with a patio area featuring a fire pit, outdoor furniture, and a covered deck with an umbrella.

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

‘The Gathering Place’: Rushville Home w/ Hot Tub
Rushville
9.4 out of 10, Exceptional, (13 reviews)
"Great stay with good location. "
United States
Emma R.
‘The Gathering Place’: Rushville Home w/ Hot Tub
A bedroom with a bed, bedside tables, a window, and a patterned rug.

4. 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 €455
includes taxes & fees
7 Sept - 8 Sept
Amazing Stargazing Retreat
A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

5. 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 €100
includes taxes & fees
13 Sept - 14 Sept
Sub Level Effiency
A modern kitchen with a large island, a sink, and a window overlooking a yard.

6. 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
8.8 out of 10, Excellent, (8 reviews)
"Very peaceful 3 days. Amenities were as expected."
United States
alan
The price is €224
includes taxes & fees
16 Sept - 17 Sept
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
A spacious living room with a grey sectional sofa, a wooden coffee table, and a kitchen in the background.

7. 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 €511
includes taxes & fees
7 Sept - 8 Sept
Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
A kitchen with wooden cabinets, a microwave, and a dining table with woven placemats.

8. 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 €267
includes taxes & fees
8 Sept - 9 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.

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

Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail
Naples
Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail
A yurt interior with a round ceiling, a mounted television, a wooden barrel, and a small kitchenette.

10. 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 €248
includes taxes & fees
8 Sept - 9 Sept
Pet Friendly Keuka Yurt
A two-story house with a driveway and landscaped yard.

11. 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 €1,565
includes taxes & fees
28 Sept - 29 Sept
PIne View Meadow
A compact kitchen with a sink, stove, and wooden cabinets.

12. 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 €312
includes taxes & fees
22 Sept - 23 Sept
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
A wooden dock extending into a body of water, with a building and greenery in the background.

13. 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 €526
includes taxes & fees
7 Sept - 8 Sept
Fall Foliage/Parent's weekend/Pets Same day bookings accepted Terms apply
A wooden cabin interior with a TV, sofa, and a view of a lake.

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 €401
includes taxes & fees
28 Sept - 29 Sept
Chipmunk Cottage | Cozy Lakefront Escape
A waterfront property with a dock, a house with a deck, and a large tree.

15. 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 €611
includes taxes & fees
7 Sept - 8 Sept
Lakeside Home - We accept direct same day bookings w VRBO booking;2 pets welcome
A large, multi-story house with a well-maintained lawn and a circular driveway.

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

Wayfinder House | Game Room • Hot Tub • Movie Room
Canandaigua
The price is €1,109
includes taxes & fees
9 Sept - 10 Sept
Wayfinder House | Game Room • Hot Tub • Movie Room
A spacious living area with a large TV, a dining table, and a kitchen area.

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 €567
includes taxes & fees
17 Sept - 18 Sept
Beautiful Sunrise Views! Quiet Keuka Lake Escape

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, (21 reviews)
"Very clean, comfortable, and welcoming."
United States
Michael
The price is €481
includes taxes & fees
7 Sept - 8 Sept
Entire Home - 4 Bedroom - Sleeps 10 Canandaigua - Steps Off Main St / Downtown
A modern kitchen with white cabinets, a black refrigerator, and a wooden floor.

19. 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 €307
includes taxes & fees
9 Sept - 10 Sept
Charming Farmhouse Retreat
A park with a covered bench, a picnic table, and a fenced area.

20. Top of the Fingerlakes, relaxing retreat.

Top of the Fingerlakes, relaxing retreat.
Waterloo
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay. "
United States
Jose
The price is €200
includes taxes & fees
7 Sept - 8 Sept
Top of the Fingerlakes, relaxing 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

41 Lakefront Hotel, Trademark Collection By Wyndham

41 Lakefront Hotel, Trademark Collection By Wyndham

10/10 Excellent
"I used the restaurant for breakfast and some dinners. Jason and Keisha were so kind and personable. This is a hotel that a I visit often. It is great for relaxation and is near other locations such as outlets, Eastview Mall, and colleges."
Benita 3-night trip
Posted 2 hours ago
41 Lakefront Hotel, Trademark Collection By Wyndham

Find out more about Middlesex

Middlesex Holiday Homes information

Number of reviews
265
Accommodation
681 Holiday Homes
Lowest Price
€100
Highest Price
€1,565