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Middlesex Holiday Rentals

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Holiday Rentals in Middlesex

Year-round, beautiful, peaceful, lake front home on Canandaigua Lake.

Middlesex
10.0 out of 10, Exceptional, (12)
"It was quiet, relaxing, and an amazing experience overall. Plenty of activities and things to do around the house and the neighborhood."
United States
Clarisa C.
The price is NZ$620
includes taxes & fees
18 Nov - 19 Nov
Year-round, beautiful, peaceful, lake front home on Canandaigua Lake.

Gypsy Belle Glamping Tent & Breakfast for 2 in Finger Lakes Wine Country!

Rushville
10.0 out of 10, Exceptional, (5)
"We loved our stay here! Our hosts went above and beyond to create a sense of community with all of the guests. And the gourmet smores!!! Oh my. Highly recommend!"
United States
Kelli M.
The price is NZ$422
includes taxes & fees
13 Nov - 14 Nov
Gypsy Belle Glamping Tent & Breakfast for 2 in Finger Lakes Wine Country!

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

Rushville
9.0 out of 10, Wonderful, (4)
"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 NZ$491
includes taxes & fees
14 Nov - 15 Nov
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

Vineyard View Farmhouse, Fire Pit, Game Room

Hammondsport
10.0 out of 10, Exceptional, (4)
"NICE LOCATION VERY CLEAN AND UPDATED. ONE BEDROOM CEILING IS VERY LOW (5 1/2 FT)AND SMALL. ALL OTHERS ARE NICE SIZE. WOULD RECOMMEND "
United States
Bobbi S.
The price is NZ$974
includes taxes & fees
10 Dec - 11 Dec
Vineyard View Farmhouse, Fire Pit, Game Room

Perfectly Located Pet-Friendly Wagon Retreat in Trendy Penn Yan, NY

Penn Yan
The price is NZ$464
includes taxes & fees
16 Nov - 17 Nov
Perfectly Located Pet-Friendly Wagon Retreat in Trendy Penn Yan, NY

The Geneva Getaway- remodeled apartment walking distance from downtown Geneva

Geneva
10.0 out of 10, Exceptional, (30)
"We enjoyed all of the amenities and cozy comfort of this getaway. Also great proximity to the lake with fun activities and dining options."
United States
Sue G.
The price is NZ$342
includes taxes & fees
2 Dec - 3 Dec
The Geneva Getaway- remodeled apartment walking distance from downtown Geneva

Sub Level Effiency

Geneva
8.8 out of 10, Excellent, (6)
"A great place to stay "
United States
Patrick
The price is NZ$166
includes taxes & fees
19 Nov - 20 Nov
Sub Level Effiency

The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

Canandaigua
10.0 out of 10, Exceptional, (79)
"Great for a short get away!"
United States
Jonathan H.
The price is NZ$450
includes taxes & fees
18 Nov - 19 Nov
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

Modern Studio APT in the Heart of Downtown Geneva

Geneva
10.0 out of 10, Exceptional, (9)
"Apartment is walking distance to lake, restaurants and shops. Property owner replies to questions and concerns promptly. "
United States
Mary T.
The price is NZ$500
includes taxes & fees
23 Nov - 24 Nov
Modern Studio APT in the Heart of Downtown Geneva

Cozy, romantic getaway on a quiet Finger Lake

Honeoye
9.8 out of 10, Exceptional, (27)
"Loved the area and the loft was nice and cozy."
United States
Anthony F.
The price is NZ$266
includes taxes & fees
13 Nov - 14 Nov
Cozy, romantic getaway on a quiet Finger Lake

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

Geneva
9.0 out of 10, Wonderful, (17)
"Great property, within walking distance of lots of great restaurants and of course the lake front. Host was friendly and communicative. Would definitely stay again!"
United States
Jessica H.
The price is NZ$337
includes taxes & fees
22 Nov - 23 Nov
Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva

Spacious ‘GEM’ of the city

Geneva
9.8 out of 10, Exceptional, (42)
"Nice stay"
United States
Anthony M.
The price is NZ$606
includes taxes & fees
20 Nov - 21 Nov
Spacious ‘GEM’ of the city

1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!

3.0 star property
Penn Yan
9.8 out of 10, Exceptional, (78)
"Great little place with everything you need. Host was very attentive with any questions we had. "
United States
Steve S.
The price is NZ$526
includes taxes & fees
13 Nov - 14 Nov
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!

Canandaigua House

Canandaigua
8.6 out of 10, Excellent, (17)
"We stayed at this house for my son‘s graduation from RIT. It offered us the perfect place to decompress. It was an easy commute back-and-forth to Rochester. However, the town offered many great sites to see and places to eat. We truly enjoyed the stay!!"
United States
Margaret S.
The price is NZ$536
includes taxes & fees
24 Nov - 25 Nov
Canandaigua House

Charming Farmhouse Retreat ~ King Suite

Shortsville
10.0 out of 10, Exceptional, (16)
"Great accommodations in a very relaxing setting. Easy to get to off the Thruway. Great central spot for exploring. Would definitely recommend."
United States
Jonathan K.
The price is NZ$684
includes taxes & fees
16 Nov - 17 Nov
Charming Farmhouse Retreat ~ King Suite

The Macberns Row House (Unit 1)

2.0 star property
Geneva
8.4 out of 10, Very good, (6)
"The set up of the unit was a bit strange, finding privacy for everyone in our family was difficult. The overall stay was good as it was just a night. Any longer than that would not have worked. "
United States
Chad
The price is NZ$760
includes taxes & fees
13 Nov - 14 Nov
The Macberns Row House (Unit 1)

Casita: Near Wineries & Keuka Lake: 100"Projector

Bath
9.6 out of 10, Exceptional, (4)
"Beautiful tiny house, it has everything you could need. Great location, very quiet and clean. We could only recommend going there, we loved it! "
United States
Manon R.
The price is NZ$334
includes taxes & fees
18 Nov - 19 Nov
Casita: Near Wineries & Keuka Lake: 100"Projector

Hubbs Cellar at JS Hubbs Guest House

Hammondsport
10.0 out of 10, Exceptional, (7)
"Very clean, quiet and convenient. Host was very nice and easy to work with as was the check-in, check-out process."
United States
Todd B.
The price is NZ$491
includes taxes & fees
16 Nov - 17 Nov
Hubbs Cellar at JS Hubbs Guest House
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

Find out more about Middlesex

Everything you need to know about Middlesex holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlesex holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesex holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesex holiday rentals we have selected for you start as low as NZ$341 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlesex rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!: This holiday home rental outside of Middlesex is located on a lake, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Middlesex?

Choose from 12 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.