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

Middlesex Holiday Rentals

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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 rentals

A lakeside setting with Adirondack chairs and a blue crate on a stone-paved area.

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 HK$2,593
HK$5,038 total
includes taxes & fees
1 Nov - 2 Nov
Peaceful lake front home with amazing views.
A group of Adirondack chairs arranged around a fire pit in a forested area with a small cabin in the background.

2. 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 HK$1,569
HK$2,196 total
includes taxes & fees
2 Nov - 3 Nov
Savannah Safari Tent & Breakfast-FLX Glamping
A yurt with a central skylight, a bed with a 'OFFLINE' sign, a woven chair, and a patterned rug.

3. 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 HK$1,372
HK$1,950 total
includes taxes & fees
1 Nov - 2 Nov
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Living area

4. 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 HK$1,216
HK$2,310 total
includes taxes & fees
17 Nov - 18 Nov
Beautiful Newly Renovated 1900s Farm House On 9 Acres
A living room with a sectional sofa, a fireplace, and a large window.

5. 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 HK$635
HK$852 total
includes taxes & fees
9 Nov - 10 Nov
Ideal location for adventure all year round
Terrace/patio

6. 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 traveller
The price is HK$353
HK$1,180 total
includes taxes & fees
27 Oct - 28 Oct
Lovely 1 Bed Ranch Close to all Attractions
A wooden deck with two Adirondack chairs, a stone wall, and a view of a lake and distant mountains.

7. 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.
Lakefront Canandaigua Home w/ Grill, Fire Pit
A modern kitchen with a stainless steel refrigerator, microwave, and stove, a bar area with stools, and a sliding glass door leading to a backyard with a barbecue grill.

8. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
4.8 out of 10, (5 reviews)
The price is HK$431
HK$632 total
includes taxes & fees
2 Nov - 3 Nov
Beautiful Tiny home Near The Lake
A cozy cabin interior with a sectional sofa, wooden ceiling, white cabinets, and a kitchenette.

9. Finger Lakes Cottage

Finger Lakes Cottage
Prattsburgh
9.8 out of 10, Exceptional, (102 reviews)
"Cute place!"
United States
Jessica W.
The price is HK$635
HK$1,326 total
includes taxes & fees
1 Nov - 2 Nov
Finger Lakes Cottage
A spacious wooden interior with large windows, a central dining table, and a chandelier.

10. 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 HK$1,491
HK$4,627 total
includes taxes & fees
9 Nov - 10 Nov
VRFLX Canandaigua View | Pool & Hot Tub
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.

11. 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.
Finger Lakes Escape • FLX Chalet + Private Pond
A spacious living room with a large wooden dining table, a blue sofa, and a fireplace.

12. 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 HK$2,061
HK$4,003 total
includes taxes & fees
27 Oct - 28 Oct
Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.
A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

13. 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 HK$459
HK$680 total
includes taxes & fees
27 Oct - 28 Oct
Sub Level Effiency
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.

14. Escape to the Heart of the Finger Lakes

Escape to the Heart of 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 traveller
The price is HK$1,365
HK$2,875 total
includes taxes & fees
27 Oct - 28 Oct
Escape to the Heart of the Finger Lakes
A yurt interior with a round ceiling, a mounted television, a wooden barrel, and a small kitchenette.

15. 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 HK$1,223
HK$1,957 total
includes taxes & fees
27 Oct - 28 Oct
Pet Friendly Keuka Yurt
A modern kitchen with a large island, a sink, and a window overlooking a yard.

16. 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 HK$918
HK$1,669 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
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 HK$1,412
HK$2,445 total
includes taxes & fees
27 Oct - 28 Oct
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
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,158
HK$2,210 total
includes taxes & fees
2 Nov - 3 Nov
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
A dining room with a table set for four, wooden chairs, a vase with flowers, and a window with curtains.

19. Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake

Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
PennYan
9.6 out of 10, Exceptional, (173 reviews)
"Pleasant stay"
United States
Aaron W.
The price is HK$1,372
HK$1,757 total
includes taxes & fees
27 Oct - 28 Oct
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
A spacious living area with a fireplace, a large flat-screen TV, and a cozy seating arrangement.

20. 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 HK$2,470
HK$4,924 total
includes taxes & fees
27 Oct - 28 Oct
Naples Oasis: 2 bedrooms, 2 baths, a full kitchen and open-concept, lake 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

Days Inn by Wyndham Geneva/Finger Lakes

Days Inn by Wyndham Geneva/Finger Lakes

8/10 Good
"It was cheap and cheerful. The room was fine. Beds were comfy and room was clean. Breakfast area was small and limited. No elevator to second floor and windows were filthy. It was close to great restaurants"
Lola 2-night trip
Posted 1 hour ago
Days Inn by Wyndham Geneva/Finger Lakes

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 holiday rentals in Middlesex?

Yes, there are holiday rentals close to the most popular sights in Middlesex, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middlesex has to offer?

Romantic Cottage-Breathtakng View-Beach Fire Pit!-Aval Sep-Oct'26-Now Booking'27: This holiday home rental outside Middlesex is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Middlesex?

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

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 wider area, you’ll find West River Marsh and Bristol Mountain Ski Resort.

What are holiday rentals like in Middlesex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlesex. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.