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

Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Middlesex vacation rentals

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 ￥51,861
￥100,778 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful lake front home with amazing views.
A yurt with a central skylight, a bed with a 'OFFLINE' sign, a woven chair, and a patterned rug.

2. Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Rushville
9.2 out of 10, Wonderful, (5 reviews)
"We so much enjoyed our two night's stay at Rainey and Jeff's campground and can't wait to return. Upon arrival, Rainey showed us around the campground, led us to our adorably decorated yurt and invited us to join the campfire later that evening for gourmet smores. We opened a bottle of wine and sat on the egg swings for a while, enjoying the sound of the bullfrogs and the beautiful surroundings. Later we enjoyed sitting by the campfire talking with the other guests and Rainey and Jeff. After a...
United States
Stephanie M.
The price is ￥27,428
￥38,619 total
includes taxes & fees
Nov 3 - Nov 4
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
A group of Adirondack chairs arranged around a fire pit in a forested area with a small cabin in the background.

3. Savannah Safari Tent & Breakfast-FLX Glamping

Savannah Safari Tent & Breakfast-FLX Glamping
Rushville
10.0 out of 10, Exceptional, (10 reviews)
"Great location, amazing hosts, wonderful morning breakfasts and coffee served! Good relaxation experience, swimming pond was awesome, going back next summer!"
United States
Faithann B.
The price is ￥31,346
￥43,884 total
includes taxes & fees
Nov 3 - Nov 4
Savannah Safari Tent & Breakfast-FLX Glamping
A cozy cabin interior with a sectional sofa, wooden ceiling, white cabinets, and a kitchenette.

4. Finger Lakes Cottage

Finger Lakes Cottage
Prattsburgh
9.8 out of 10, Exceptional, (102 reviews)
"Cute place!"
United States
Jessica W.
The price is ￥12,706
￥26,529 total
includes taxes & fees
Nov 1 - Nov 2
Finger Lakes Cottage
Living area

5. Lovely 1 Bed Ranch Close to all Attractions

Lovely 1 Bed Ranch Close to all Attractions
Canandaigua NY
4.0 out of 10, (1 review)
"There is NO house number on the building. The host did NOT provide us with info prior to arrival, we had to message him to get access. It appeared that check in was at 4:00, but turned out it was 3:00. The actual property appearance does NOT look like the pictures online. Outside is overgrown, dirty and cobweb’s everywhere. Inside smells musty and gross. Flies everywhere, spiders in the bathroom and shower. It was not clean under the bed. There’s no bathroom soaps or wash clothes and the towels...
United States
Anonymous traveler
The price is ￥7,059
￥23,609 total
includes taxes & fees
Oct 25 - Oct 26
Lovely 1 Bed Ranch Close to all Attractions
Interior

6. Beautiful Newly Renovated 1900s Farm House On 9 Acres

Beautiful Newly Renovated 1900s Farm House On 9 Acres
Rushville
7.0 out of 10, Good, (2 reviews)
"Beautiful, private, place. We loved the outdoor fire. The bed was very comfortable. We had everything we needed."
United States
ERIC W.
The price is ￥14,106
￥33,177 total
includes taxes & fees
Oct 28 - Oct 29
Beautiful Newly Renovated 1900s Farm House On 9 Acres
A living room with a brown leather sofa, a wooden coffee table, a TV mounted on the wall, and a window with blinds.

7. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
4.8 out of 10, (5 reviews)
The price is ￥11,765
￥16,021 total
includes taxes & fees
Nov 5 - Nov 6
Beautiful Tiny home Near The Lake
A living room with a sectional sofa, a fireplace, and a large window.

8. Ideal location for adventure all year round

Ideal location for adventure all year round
Naples
10.0 out of 10, Exceptional, (9 reviews)
"The space was perfectly clean, comfortable, and convenient. I would definitely stay here again!"
United States
Andrew A.
The price is ￥13,271
￥17,638 total
includes taxes & fees
Nov 5 - Nov 6
Ideal location for adventure all year round
A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

9. Sub Level Effiency

Sub Level Effiency
Geneva
8.8 out of 10, Excellent, (20 reviews)
"A great place to stay "
United States
Patrick
The price is ￥9,169
￥13,597 total
includes taxes & fees
Oct 27 - Oct 28
Sub Level Effiency
A wooden deck with two Adirondack chairs, a stone wall, and a view of a lake and distant mountains.

10. Lakefront Canandaigua Home w/ Grill, Fire Pit

Lakefront Canandaigua Home w/ Grill, Fire Pit
Canandaigua
9.8 out of 10, Exceptional, (37 reviews)
"Highly recommend! Great stay and very beautiful area."
United States
A.G.A. N.
The price is ￥24,158
￥62,028 total
includes taxes & fees
Oct 30 - Oct 31
Lakefront Canandaigua Home w/ Grill, Fire Pit
A space-themed RV with a blue exterior, two chairs, and a fire pit in a gravel area.

11. 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, (11 reviews)
"Very peaceful 3 days. Amenities were as expected."
United States
alan
The price is ￥18,337
￥33,352 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
A spacious wooden interior with large windows, a central dining table, and a chandelier.

12. 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 ￥30,020
￥93,378 total
includes taxes & fees
Oct 27 - Oct 28
VRFLX Canandaigua View | Pool & Hot Tub
A modern living room with a sectional sofa, a dining table with chairs, a kitchen area, and a large window with a view of trees.

13. Cozy 1BDR APT in Vibrant Downtown Geneva

Cozy 1BDR APT in Vibrant Downtown Geneva
Geneva
9.8 out of 10, Exceptional, (20 reviews)
"The apartment was adorable. Perfect place to stay for our needs. Ryan was great and very responsive to my emails. Would definitely stay here again!"
United States
Stacey L.
The price is ￥15,516
￥43,270 total
includes taxes & fees
Oct 25 - Oct 26
Cozy 1BDR APT in Vibrant Downtown Geneva
A modern living room with a sliding barn door, a gray armchair, a wooden coffee table, and a gray sofa with patterned throw blankets.

14. The Geneva Getaway- remodeled apartment walking distance from downtown Geneva

The Geneva Getaway- remodeled apartment walking distance from downtown Geneva
Geneva
10.0 out of 10, Exceptional, (33 reviews)
"Great stay. Had all we needed!"
United States
Melissa N.
The price is ￥12,695
￥29,790 total
includes taxes & fees
Nov 4 - Nov 5
The Geneva Getaway- remodeled apartment walking distance from downtown Geneva
A spacious living room with a large wooden dining table, a blue sofa, and a fireplace.

15. Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.

Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.
Canandaigua
10.0 out of 10, Exceptional, (26 reviews)
"Everything was wonderful. Only comment I have is the “lake view” is just a small view between 2 houses across the street."
United States
John
The price is ￥41,189
￥79,997 total
includes taxes & fees
Oct 26 - Oct 27
Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.
A yurt interior with a round ceiling, a mounted television, a wooden barrel, and a small kitchenette.

16. 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 ￥24,439
￥39,109 total
includes taxes & fees
Oct 27 - Oct 28
Pet Friendly Keuka Yurt
A kitchen with wooden cabinets, a microwave, and a dining table with woven placemats.

17. 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 ￥28,211
￥48,862 total
includes taxes & fees
Oct 27 - Oct 28
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
A compact kitchen with a sink, stove, and wooden cabinets.

18. 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 ￥23,557
￥44,990 total
includes taxes & fees
Nov 16 - Nov 17
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
A modern kitchen with wooden beams, a dining area with a glass table, and a cozy living room with a sofa.

19. Modern Studio APT in the Heart of Downtown Geneva

Modern Studio APT in the Heart of Downtown Geneva
Geneva
10.0 out of 10, Exceptional, (23 reviews)
"Great property, location and host!"
United States
Michele A.
The price is ￥18,102
￥46,741 total
includes taxes & fees
Oct 29 - Oct 30
Modern Studio APT in the Heart of Downtown Geneva
A kitchen with a gas stove, oven, microwave, and a stainless steel refrigerator. There are potted plants on the counter and a sign on the wall.

20. One bedroom apartment in the finger lakes

One bedroom apartment in the finger lakes
Naples
10.0 out of 10, Exceptional, (4 reviews)
"I enjoyed my stay. The host left a nice welcome card was very easy to communicate with."
United States
Anonymous traveler
The price is ￥27,741
￥58,128 total
includes taxes & fees
Oct 27 - Oct 28
One bedroom apartment in the finger lakes
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 The Hammondsport Hotel

Best Western Plus The Hammondsport Hotel

10/10 Excellent
"Staff always ready to go beyond the ordinary. Helpful and eager to please your needs."
anthony 1-night trip
Posted 13 hours ago
Best Western Plus The Hammondsport Hotel

Find out more about Middlesex

Search for holiday rentals in Middlesex on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesex using one of the methods below:

  • View our selection of featured holiday rentals in Middlesex
  • Use the map to find apartments and other holiday homes in the Middlesex neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesex while they last

Look no further and take a look at our great range of rental properties in Middlesex!

Frequently asked questions

Are there vacation rentals in Middlesex?

Yes, we offer vacation rentals near popular attractions in Middlesex, or you can go with a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Middlesex?

Romantic Cottage-Breathtakng View-Beach Fire Pit!-Aval Sep-Oct'26-Now Booking'27: This vacation home rental outside Middlesex is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Middlesex?

Choose from 11 Expedia vacation rentals in Middlesex for a memorable vacation.

What can I see and do in Middlesex?

Canandaigua Lake and Clarks Gully are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find West River Marsh and Bristol Mountain Ski Resort.

What are vacation rentals like in Middlesex?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Middlesex. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip.