A pier with a red lighthouse at dusk, reflecting on calm water.

Holiday Homes in Middlesex

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Middlesex holiday homes

A room with a large window overlooking a body of water, wicker furniture, and a patterned rug.

1. Peaceful lake front home with amazing views.

Peaceful lake front home with amazing views.
Middlesex
10.0 out of 10, Exceptional, (27 reviews)
"Very quiet and peaceful when we were there ."
United States
Julie Z.
The price is AU$914
includes taxes & fees
1 Nov - 2 Nov
Peaceful lake front home with amazing views.
A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

2. Sub Level Effiency

Sub Level Effiency
Geneva
9.0 out of 10, Wonderful, (21 reviews)
"A great place to stay "
United States
Patrick
The price is AU$142
includes taxes & fees
1 Nov - 2 Nov
Sub Level Effiency
A spacious wooden interior with large windows, a central dining table, and a chandelier.

3. VRFLX Canandaigua View | Pool & Hot Tub

VRFLX Canandaigua View | Pool & Hot Tub
Naples
10.0 out of 10, Exceptional, (103 reviews)
"We traveled with family and our infant. It was a beautiful home and property. "
United States
Marina V.
The price is AU$847
includes taxes & fees
2 Nov - 3 Nov
VRFLX Canandaigua View | Pool & Hot Tub
A yurt interior with a round ceiling, a mounted television, a wooden barrel, and a small kitchenette.

4. Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, Exceptional, (30 reviews)
"Such a fun yurt and a peaceful location! We loved the proximity to activities and then relaxing with a glass of wine on the little balcony!"
United States
Sharon
The price is AU$360
includes taxes & fees
2 Nov - 3 Nov
Pet Friendly Keuka Yurt
A modern kitchen with a large island, a sink, and a window overlooking a yard.

5. 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
8.2 out of 10, Very good, (12 reviews)
"Very peaceful 3 days. Amenities were as expected."
United States
alan
The price is AU$327
includes taxes & fees
9 Nov - 10 Nov
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
A modern living room with a green sofa, a wooden floor, and a large sliding glass door leading to an outdoor deck with chairs and a table.

6. Finger Lakes Escape • FLX Chalet + Private Pond

Finger Lakes Escape • FLX Chalet + Private Pond
Branchport
10.0 out of 10, Exceptional, (11 reviews)
"Great place for a winter getaway!"
United States
Catherine K.
The price is AU$629
includes taxes & fees
22 Nov - 23 Nov
Finger Lakes Escape • FLX Chalet + Private Pond
A kitchen with wooden cabinets, a microwave, and a dining table with woven placemats.

7. 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, (89 reviews)
"Everything you need, very nice base for exploring the finger lakes."
United States
Adam R.
The price is AU$432
includes taxes & fees
1 Nov - 2 Nov
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
A compact kitchen with a sink, stove, and wooden cabinets.

8. 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
10.0 out of 10, Exceptional, (1 review)
The price is AU$391
includes taxes & fees
2 Nov - 3 Nov
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
A spacious living area with a fireplace, a large flat-screen TV, and a cozy seating arrangement.

9. Naples Oasis: 2 bedrooms, 2 baths, a full kitchen and open-concept, lake views!

Naples Oasis: 2 bedrooms, 2 baths, a full kitchen and open-concept, lake views!
Naples
The price is AU$888
includes taxes & fees
16 Nov - 17 Nov
Naples Oasis: 2 bedrooms, 2 baths, a full kitchen and open-concept, lake views!
A spacious living room with hardwood flooring, a ceiling fan, a large window with a view, and a leather couch.

10. Canandaigua Lake Overlook

Canandaigua Lake Overlook
Canandaigua
8.6 out of 10, Excellent, (7 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 AU$938
includes taxes & fees
3 Nov - 4 Nov
Canandaigua Lake Overlook
A spacious room with wooden flooring, wicker furniture, and large windows allowing natural light.

11. Wine Country: Epic Game Room, Lake Views, Fire Pit

Wine Country: Epic Game Room, Lake Views, Fire Pit
Naples
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay. Highly recommend."
United States
Maffettone Thiesmeyer T.
The price is AU$1,309
includes taxes & fees
3 Nov - 4 Nov
Wine Country: Epic Game Room, Lake Views, Fire Pit
A modern kitchen with a central island, wooden chairs, and green cabinetry.

12. 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, (13 reviews)
"We rented the property to attend a wedding and found out that the wedding venue was only 2 minutes away! Great location with nice views all around. Very quiet at night and nice comfortable beds for a good nights sleep. Great place to stay for a long weekend or a full weeks vacation."
United States
Brian K.
The price is AU$594
includes taxes & fees
30 Oct - 31 Oct
Charming country ranch in the hills of the Finger Lakes
A deck with a hot tub, a hanging hammock, and a view of the landscape.

13. Amazing Stargazing Retreat

Amazing Stargazing Retreat
Naples
9.6 out of 10, Exceptional, (7 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.
Amazing Stargazing Retreat
A living room with two grey sofas, a coffee table, a lamp, and a small wooden side table.

14. A Relaxing Getaway on Grant in Geneva.

A Relaxing Getaway on Grant in Geneva.
Geneva
The price is AU$392
includes taxes & fees
3 Nov - 4 Nov
A Relaxing Getaway on Grant in Geneva.
A spacious living room with a grey sectional sofa, a wooden coffee table, and a kitchen in the background.

15. 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, (2 reviews)
"House was exactly as advertised and worked perfectly for 7 travelers. The firepit outdoors was great and house was very walkable to everything Naples had to offer. The kitchen had everything you needed to cook and serve. House was clean and the owner was super responsive and accommodating. I would highly recommend this house to any group traveling to the Naples area."
United States
Michael T.
The price is AU$804
includes taxes & fees
30 Oct - 31 Oct
Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
A spacious kitchen with a large island, wooden ceiling beams, and large windows offering a view.

16. Enjoy Cabin Vibes & Lake Views, Close to Town, Lake & FLX Activities; EV Charger

Enjoy Cabin Vibes & Lake Views, Close to Town, Lake & FLX Activities; EV Charger
Canandaigua
10.0 out of 10, Exceptional, (41 reviews)
"We had a wonderful stay at this beautiful home on Lake Canandaigua! The house was spotless, well-maintained, and had everything we needed for a relaxing and enjoyable vacation. We loved grilling out for BBQ dinners and spending the evenings around the fire pit making s’mores with the family. The lake views were absolutely stunning, and the location was perfect—close to everything while still feeling peaceful and private. We would definitely stay here again and highly recommend it!"
United States
Wendy B.
The price is AU$1,158
includes taxes & fees
1 Nov - 2 Nov
Enjoy Cabin Vibes & Lake Views, Close to Town, Lake & FLX Activities; EV Charger
A spacious living area with a high ceiling, a fireplace, and a television.

17. The Vita and Vine: Lakefront, Outdoor Theater

The Vita and Vine: Lakefront, Outdoor Theater
Rushville
The price is AU$1,323
includes taxes & fees
1 Nov - 2 Nov
The Vita and Vine: Lakefront, Outdoor Theater
A park with a covered bench, a picnic table, and a fenced area.

18. Top of the Fingerlakes, relaxing retreat.

Top of the Fingerlakes, relaxing retreat.
Waterloo
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay. "
United States
Jose
The price is AU$315
includes taxes & fees
1 Nov - 2 Nov
Top of the Fingerlakes, relaxing retreat.
A bedroom with a view of a lake through a sliding glass door.

19. Fall Foliage/Hiking/Wine Tasting/Pets Same day bookings accepted Terms apply

Fall Foliage/Hiking/Wine Tasting/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 AU$730
includes taxes & fees
1 Nov - 2 Nov
Fall Foliage/Hiking/Wine Tasting/Pets Same day bookings accepted Terms apply
A spacious living area with a large sofa, a ceiling fan, skylights, a flat-screen TV, and a wooden floor.

20. Secluded Finger Lakes 3BR Retreat Near Keuka Lake with Vineyard Views

Secluded Finger Lakes 3BR Retreat Near Keuka Lake with Vineyard Views
Branchport
9.2 out of 10, Wonderful, (5 reviews)
"Such a great stay! Highly recommended"
United States
Kymberlee D.
The price is AU$624
includes taxes & fees
2 Nov - 3 Nov
Secluded Finger Lakes 3BR Retreat Near Keuka Lake with Vineyard Views
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

Hampton Inn Penn Yan

Hampton Inn Penn Yan

10/10 Excellent
"The hotel location is perfect, overlooking the lake. Best to reserve a lake view room."
eric 3-night trip
Posted 4 hours ago
Hampton Inn Penn Yan

Find out more about Middlesex

Middlesex Holiday Homes information

Number of reviews
401
Accommodation
683 Holiday Homes
Lowest Price
AU$142
Highest Price
AU$1,323