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

Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Middlesex vacation rentals

Exterior

Timber Haven - Serene year-round log home getaway with gas fireplace, HVAC, WiFi

Timber Haven - Serene year-round log home getaway with gas fireplace, HVAC, WiFi
Cohocton
10.0 out of 10, Exceptional, (47 reviews)
"This cabin is amazing, very comfortable relaxing. "
United States
Nikki F.
The price is ￥32,410
￥41,381 total
includes taxes & fees
Jul 13 - Jul 14
Timber Haven - Serene year-round log home getaway with gas fireplace, HVAC, WiFi
Smart TV

Private Seneca Lake View Cabin, Walkable, Wineries, Fire Pit, Near Geneva!

Private Seneca Lake View Cabin, Walkable, Wineries, Fire Pit, Near Geneva!
Geneva
9.8 out of 10, Exceptional, (46 reviews)
"Cabin was nice and cozy, settled on 2.1 acres with several other cabins nearby and it was very quiet, warm and relaxing overlooking Seneca Lake and nature blessed me with some light snowfall with several deer passing through the property. "
United States
JES
Private Seneca Lake View Cabin, Walkable, Wineries, Fire Pit, Near Geneva!
Microwave, oven, stovetop, dishwasher

Lakeview and relax at the heart of Seneca lake

Lakeview and relax at the heart of Seneca lake
Geneva
9.8 out of 10, Exceptional, (12 reviews)
"This was a wonderful place. It was very clean and comfortable. We would definitely stay here again. "
United States
Rev John S.
The price is ￥46,832
￥87,103 total
includes taxes & fees
Jul 14 - Jul 15
Lakeview and relax at the heart of Seneca lake
Property grounds

Cozy Cottage with 45' Lake Frontage and Kayaks

Cozy Cottage with 45' Lake Frontage and Kayaks
Lodi
9.6 out of 10, Exceptional, (97 reviews)
"Loved everything"
United States
Syes S.
The price is ￥54,287
￥83,283 total
includes taxes & fees
Jul 14 - Jul 15
Cozy Cottage with 45' Lake Frontage and Kayaks
Interior

Kellys Suite

Kellys Suite
Geneva
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful apartment! Safe neighborhood and had a great stay, love the decorating!"
United States
Amanda G.
The price is ￥34,841
￥56,228 total
includes taxes & fees
Jul 15 - Jul 16
Kellys Suite
Fridge, microwave, oven, stovetop

Private Rural Getaway

Private Rural Getaway
Springwater
10.0 out of 10, Exceptional, (18 reviews)
"Very clean, spacious and lots of beds."
Canada
Daniel
The price is ￥51,694
￥73,167 total
includes taxes & fees
Aug 4 - Aug 5
Private Rural Getaway
Property grounds

Peaceful, pet friendly and newly remodeled Geneva home

Peaceful, pet friendly and newly remodeled Geneva home
Geneva
9.8 out of 10, Exceptional, (27 reviews)
"Very comfortable and dog friendly which was great!"
United States
Matthew W.
The price is ￥28,382
￥48,209 total
includes taxes & fees
Jul 21 - Jul 22
Peaceful, pet friendly and newly remodeled Geneva home
Interior

FLX Solar Powered Village/Tunnel to Seneca Lake!

FLX Solar Powered Village/Tunnel to Seneca Lake!
Geneva
10.0 out of 10, Exceptional, (20 reviews)
"Great place to stay while doing wine tasting! "
United States
Jason V.
FLX Solar Powered Village/Tunnel to Seneca Lake!
Smart TV

2 Acre Finger Lakes Lakeview Cabin - Fire Pit and Grill - Near Geneva Wineries!

2 Acre Finger Lakes Lakeview Cabin - Fire Pit and Grill - Near Geneva Wineries!
Geneva
9.8 out of 10, Exceptional, (74 reviews)
"We had a wonderful stay! Everything was as described, it was clean, sheets and towels smelled lovely, and the space was perfectly described. Super convenient location to a ton of wineries. The firepit was so pleasant. Thank you for a fabulous getaway!"
United States
Lisa C.
2 Acre Finger Lakes Lakeview Cabin - Fire Pit and Grill - Near Geneva Wineries!
Dining

Sub Level Effiency

Sub Level Effiency
Geneva
8.4 out of 10, Very Good, (11 reviews)
"A great place to stay "
United States
Patrick
The price is ￥10,509
￥15,196 total
includes taxes & fees
Jul 12 - Jul 13
Sub Level Effiency
Property grounds

Charming 3-bedroom cottage with AC in Penn Yan

Charming 3-bedroom cottage with AC in Penn Yan
Penn Yan
10.0 out of 10, Exceptional, (1 review)
"This house was excellent. Very clean and had a well-stocked kitchen with everything you need. Also had plenty of towels for the family. The beds were very comfortable and it’s very quiet. Very easy to get to Penn Yan by car in a few minutes. We will definitely rent this property again."
United States
Amie M.
The price is ￥43,024
￥70,692 total
includes taxes & fees
Jul 9 - Jul 10
Charming 3-bedroom cottage with AC in Penn Yan
Exterior

Charming 4 BD near DT Geneva

Charming 4 BD near DT Geneva
Geneva
9.8 out of 10, Exceptional, (10 reviews)
"Would stay again"
United States
Christi D.
The price is ￥64,658
￥81,476 total
includes taxes & fees
Jul 14 - Jul 15
Charming 4 BD near DT Geneva
Fridge, microwave, oven, stovetop

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, (81 reviews)
"This is the second time I’ve stayed here, great experience both times."
United States
Deanna S.
The price is ￥29,169
￥50,869 total
includes taxes & fees
Jul 12 - Jul 13
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Pool

Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
Penn Yan
9.8 out of 10, Exceptional, (153 reviews)
"The cabin and property was perfect for us, the only negative was a lack of water pressure using the shower."
United States
Jeffrey
The price is ￥23,516
￥29,971 total
includes taxes & fees
Aug 2 - Aug 3
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
Interior

Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, Exceptional, (28 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 ￥34,627
￥49,626 total
includes taxes & fees
Jul 9 - Jul 10
Pet Friendly Keuka Yurt
Terrace/patio

Cozy All Season Bungalow right on the Lake wine and brewery trail.

Cozy All Season Bungalow right on the Lake wine and brewery trail.
Penn Yan
9.6 out of 10, Exceptional, (50 reviews)
"The place was beautiful and in a great location. We really enjoyed our stay. "
United States
Alanna B.
The price is ￥37,910
￥65,164 total
includes taxes & fees
Jul 20 - Jul 21
Cozy All Season Bungalow right on the Lake wine and brewery trail.
Exterior

Cayuga Cottage [Bella Vista Cottages]

Cayuga Cottage [Bella Vista Cottages]
Geneva
9.6 out of 10, Exceptional, (17 reviews)
"We loved the location, the views and how spacious the house was. "
United States
Kyle
The price is ￥84,225
￥130,231 total
includes taxes & fees
Jul 9 - Jul 10
Cayuga Cottage [Bella Vista Cottages]
Smart TV

Naples Wine Country 5BR • Sleeps 16 • Hot Tub • Near Bristol Mountain Ski Resort

Naples Wine Country 5BR • Sleeps 16 • Hot Tub • Near Bristol Mountain Ski Resort
Naples
10.0 out of 10, Exceptional, (1 review)
The price is ￥22,971
￥77,592 total
includes taxes & fees
Jul 13 - Jul 14
Naples Wine Country 5BR • Sleeps 16 • Hot Tub • Near Bristol Mountain Ski Resort
Terrace/patio

The Wheat House on Main (Unit 4, 2nd story))

The Wheat House on Main (Unit 4, 2nd story))
Geneva
8.6 out of 10, Excellent, (4 reviews)
"We had a wonderful stay with our adult children. It was a nice space to cook, eat & relax together. We walked into town for coffee and enjoyed the quaint shops. We really love the wineries & breweries. We will definitely be back!"
United States
Elizabeth S.
The price is ￥60,161
￥103,391 total
includes taxes & fees
Jul 9 - Jul 10
The Wheat House on Main (Unit 4, 2nd story))
Smart TV

Cozy 1BDR APT in Vibrant Downtown Geneva

Cozy 1BDR APT in Vibrant Downtown Geneva
Geneva
10.0 out of 10, Exceptional, (12 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 ￥18,143
￥42,271 total
includes taxes & fees
Jul 14 - Jul 15
Cozy 1BDR APT in Vibrant Downtown Geneva
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
"Clean room and great breakfast"
Lucas 2-night trip
Posted 6 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:

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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?

A dreamy Seneca Lake retreat with sweeping views, a relaxing hot tub under the stars, flexible bedroom setups, a fully stocked kitchen, cozy living spaces, and easy access to the lake, wineries, and waterfalls.: This vacation home rental outside of Middlesex is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the hot tub in this rental home to help you unwind.

How many vacation rentals will I find in Middlesex?

Choose from 12 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.