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Check prices for these dates

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

Our top choices for Middlesex vacation homes

Dining

1. VRFLX Canandaigua View | Pool & Hot Tub

VRFLX Canandaigua View | Pool & Hot Tub
Naples
10.0 out of 10, Exceptional, (102 reviews)
"We traveled with family and our infant. It was a beautiful home and property. "
United States
Marina V.
The price is ￥38,823
￥101,255 total
includes taxes & fees
Sep 28 - Sep 29
VRFLX Canandaigua View | Pool & Hot Tub
Dining

2. 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 ￥11,013
￥15,638 total
includes taxes & fees
Sep 21 - Sep 22
Sub Level Effiency
Coffee/tea maker, fridge, microwave, oven

3. 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 ￥35,298
￥67,937 total
includes taxes & fees
Sep 21 - Sep 22
Charming country ranch in the hills of the Finger Lakes
Interior

4. 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 ￥44,629
￥125,386 total
includes taxes & fees
Sep 28 - Sep 29
Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail
Smart TV, books

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, Exceptional, (1 review)
The price is ￥30,345
￥85,087 total
includes taxes & fees
Sep 21 - Sep 22
Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
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 ￥45,338
￥104,540 total
includes taxes & fees
Sep 21 - Sep 22
‘The Gathering Place’: Rushville Home w/ Hot Tub
Coffee/tea maker, fridge, oven, stovetop

7. 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 ￥18,073
￥33,069 total
includes taxes & fees
Sep 26 - Sep 27
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
TV

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

Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
Canandaigua
8.4 out of 10, Very good, (6 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 ￥33,415
￥82,300 total
includes taxes & fees
Oct 20 - Oct 21
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
Outdoor spa tub

9. 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 ￥50,346
￥78,402 total
includes taxes & fees
Sep 27 - Sep 28
Amazing Stargazing Retreat
Terrace/patio

10. The Vita and Vine: Lakefront, Outdoor Theater

The Vita and Vine: Lakefront, Outdoor Theater
Rushville
The price is ￥56,053
￥138,679 total
includes taxes & fees
Oct 13 - Oct 14
The Vita and Vine: Lakefront, Outdoor Theater
Property grounds

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, 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 ￥35,298
￥95,455 total
includes taxes & fees
Sep 21 - Sep 22
Fall Foliage/Parent's weekend/Pets Same day bookings accepted Terms apply
TV, DVD player

12. 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 ￥16,159
￥64,340 total
includes taxes & fees
Sep 29 - Sep 30
Chipmunk Cottage | Cozy Lakefront Escape
Interior

13. 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 ￥28,538
￥43,749 total
includes taxes & fees
Sep 21 - Sep 22
Pet Friendly Keuka Yurt
Coffee/tea maker, fridge, microwave, oven

14. 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 ￥28,238
￥48,909 total
includes taxes & fees
Sep 21 - Sep 22
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Interior

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 ￥23,579
￥44,681 total
includes taxes & fees
Oct 12 - Oct 13
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
Exterior

16. 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 ￥101,501
￥256,051 total
includes taxes & fees
Sep 22 - Sep 23
PIne View Meadow
Exterior

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

Wayfinder House | Game Room • Hot Tub • Movie Room
Canandaigua
10.0 out of 10, Exceptional, (1 review)
"We were a group of 10 women, all 65, and we had such a wonderful stay! The home was a great place for our girls’ getaway, and we really enjoyed our time there. It was comfortable, welcoming, and gave us a wonderful space to relax, laugh, and make memories together.As someone who stays in at least 12 VRBOs and Airbnbs a year—approximately four months out of the year—I’ve experienced quite a few vacation rentals. I wanted to share a few little suggestions simply because I think this property has...
United States
Brenda C.
The price is ￥37,337
￥182,195 total
includes taxes & fees
Sep 22 - Sep 23
Wayfinder House | Game Room • Hot Tub • Movie Room
Exterior

18. 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 ￥49,613
￥136,782 total
includes taxes & fees
Sep 21 - Sep 22
Lakeside Home - We accept direct same day bookings w VRBO booking;2 pets welcome
Interior

19. 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 ￥45,887
￥87,110 total
includes taxes & fees
Sep 21 - Sep 22
Entire Home - 4 Bedroom - Sleeps 10 Canandaigua - Steps Off Main St / Downtown
Outdoor dining

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

Canadaigua Lake Sunset Oasis: Private Beach, Family Fun Wineries, CMAC, Shopping
Canandaigua
9.8 out of 10, Exceptional, (20 reviews)
"Gorgeous view. Comfortable beds. Great stay "
United States
Sara L.
The price is ￥78,283
￥152,963 total
includes taxes & fees
Oct 13 - Oct 14
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

Best Western Plus Vineyard Inn & Suites

Best Western Plus Vineyard Inn & Suites

10/10 Excellent
"Kind and helpful staff. Breakfast was great. Location was close to many things including a few restaurants within walking distance."
Debbie 3-night trip
Posted 12 hours ago
Best Western Plus Vineyard Inn & Suites

Find out more about Middlesex

Middlesex Vacation Homes information

Number of reviews
6,190
Accommodation
684 Vacation Homes
Lowest Price
￥13,852
Highest Price
￥63,227