Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Middlesex vacation rentals

Terrace/patio

Cozy new England style cottage Right on Wine and Beer Trail

Cozy new England style cottage Right on Wine and Beer Trail
Penn Yan
9.6 out of 10, Exceptional, (285 reviews)
"Such a cozy little spot! Would love to visit again"
United States
Paola R.
Cozy new England style cottage Right on Wine and Beer Trail
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, (45 reviews)
"The stay was excellent… quiet with room to workout outside. Great view and responsive and proactive host."
United States
Sylvester F.
The price is ￥15,759
￥57,840 total
includes taxes & fees
May 26 - May 27
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
9.6 out of 10, Exceptional, (10 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 ￥45,951
￥85,634 total
includes taxes & fees
May 25 - May 26
Lakeview and relax at the heart of Seneca lake
Dining

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, (37 reviews)
"Clean. Nicely decorated"
United States
Jordan K.
The price is ￥47,541
￥105,803 total
includes taxes & fees
May 24 - May 25
Enjoy Cabin Vibes & Lake Views, Close to Town, Lake & FLX Activities; EV Charger
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, (150 reviews)
"Great location to hikes, wineries and restaurants.Highly recommend!"
United States
Roger B.
The price is ￥20,750
￥26,802 total
includes taxes & fees
May 25 - May 26
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
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, (80 reviews)
"This is the second time I’ve stayed here, great experience both times."
United States
Deanna S.
The price is ￥28,620
￥49,056 total
includes taxes & fees
May 27 - May 28
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Terrace/patio

The Wheat House on Main (1ST Story Unit)

The Wheat House on Main (1ST Story Unit)
Geneva
10.0 out of 10, Exceptional, (6 reviews)
"It was a great house. The host was very responsive and accommodating. "
United States
Julie S.
The price is ￥51,158
￥93,223 total
includes taxes & fees
May 25 - May 26
The Wheat House on Main (1ST Story Unit)
Fridge, microwave, oven, stovetop

Private Rural Getaway

Private Rural Getaway
Springwater
10.0 out of 10, Exceptional, (15 reviews)
"Very clean, spacious and lots of beds."
Canada
Daniel
The price is ￥40,068
￥58,970 total
includes taxes & fees
May 26 - May 27
Private Rural Getaway
Outdoor dining

Between Geneva & Canandaigua- Large Yard, Firepit, Sleeps 13

Between Geneva & Canandaigua- Large Yard, Firepit, Sleeps 13
Stanley
9.4 out of 10, Exceptional, (16 reviews)
"Wonderful weekend getaway!"
United States
Jill C.
Between Geneva & Canandaigua- Large Yard, Firepit, Sleeps 13
Dining

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, (152 reviews)
"Super clean, everything we needed, kind and considerate host, a quiet, refreshing step back it time!"
United States
Janie K.
The price is ￥27,825
￥35,438 total
includes taxes & fees
May 25 - May 26
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
Interior

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, (22 reviews)
"A cozy and comfortable cottage, great location and a relaxing stay!"
United States
Kathy G.
The price is ￥41,785
￥80,471 total
includes taxes & fees
May 24 - May 25
Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.
Exterior

Sunny Trails Getaway Cabin

Sunny Trails Getaway Cabin
Cohocton
10.0 out of 10, Exceptional, (13 reviews)
"great vacation home! dogs had so much fun running through the woods. we will definitely visit again!"
United States
Richard M.
Sunny Trails Getaway Cabin
House (3 Bedrooms) | Interior

Keuka Lake Retreat Steps From Marina!

Keuka Lake Retreat Steps From Marina!
3.0 star property
Penn Yan
The price is ￥45,474
￥99,402 total
includes taxes & fees
Jun 8 - Jun 9
Keuka Lake Retreat Steps From Marina!
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, (26 reviews)
"Very comfortable and dog friendly which was great!"
United States
Matthew W.
The price is ￥27,857
￥47,317 total
includes taxes & fees
May 26 - May 27
Peaceful, pet friendly and newly remodeled Geneva home
Property grounds

Cozy Cabin With 165 Ft Beach and wood-fired hot tub! Center of FLX wine country!

Cozy Cabin With 165 Ft Beach and wood-fired hot tub! Center of FLX wine country!
Penn Yan
10.0 out of 10, Exceptional, (262 reviews)
"House was cozy and well-equipped, wood-fired hot tub and beach/pier areas were awesome!"
United States
William F.
Cozy Cabin With 165 Ft Beach and wood-fired hot tub! Center of FLX wine country!
Property grounds

Lakeside cottage on quiet, private road. Walk to Keuka Lake State Park!

Lakeside cottage on quiet, private road. Walk to Keuka Lake State Park!
Keuka Park
10.0 out of 10, Exceptional, (255 reviews)
"Had a great quiet weekend getaway!"
United States
Dan Y.
The price is ￥27,030
￥50,931 total
includes taxes & fees
Jun 2 - Jun 3
Lakeside cottage on quiet, private road. Walk to Keuka Lake State Park!
Interior

Cottage with lake view at the heart of Seneca lake

Cottage with lake view at the heart of Seneca lake
Geneva
9.6 out of 10, Exceptional, (7 reviews)
"We had a great time and the cottage was charming. The location was convenient, and we had a nice view of the lake. Very enjoyable weekend! "
United States
MaryJo C.
The price is ￥41,356
￥79,667 total
includes taxes & fees
May 24 - May 25
Cottage with lake view at the heart of Seneca lake
Outdoor dining

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, (39 reviews)
"Loved the cabin We had a great stay"
United States
Sue T.
The price is ￥28,620
￥36,328 total
includes taxes & fees
May 25 - May 26
Timber Haven - Serene year-round log home getaway with gas fireplace, HVAC, WiFi
Outdoor dining

Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva

Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva
Geneva
9.0 out of 10, Wonderful, (22 reviews)
"Communication was good and the place was clean and cozy. The apartment is on the 3rd floor up a couple flights of stairs. The heat worked well and the kitchen had a decent amount of amenities. It’s located right in downtown Geneva which was super convenient. I would stay here again. "
United States
Susan P.
The price is ￥21,465
￥32,856 total
includes taxes & fees
May 25 - May 26
Cozy 1-bedroom apartment with AC and WiFi in enjoyable 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

The Lake House on Canandaigua

The Lake House on Canandaigua

8/10 Good
"Very easy check in, staff was very courteous and professional. The room was very well stocked . We only stayed one night and did not get to use the amenities. Grounds were lovely."
Melissa 1-night trip
Posted less than an hour ago
The Lake House on Canandaigua

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
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  • 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?

Cozy Cabin With 165 Ft Beach and wood-fired hot tub! Center of FLX wine country!: This vacation home rental outside of Middlesex is located on the beach and has a balcony, 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. You and your friends and family can relax into your vacation with amenities like a hot tub.

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.