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Middlesex Vacation Rentals

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Vacation Rentals in Middlesex

Timber Haven - Serene log home getaway with Wi-Fi, AC in NY Finger Lakes

Cohocton
10.0 out of 10, Exceptional, (13)
"Great property with a wonderful host!!!!"
United States
Scott M.
$172 nightly
The price is $193
Nov 20 - Nov 21
Total with taxes and fees
Timber Haven - Serene log home getaway with Wi-Fi, AC in NY Finger Lakes

Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..

Naples
8.6 out of 10, Excellent, (227)
"Very private, quiet getaway! The cottage was very cute tucked away in the woods. It was very peaceful."
United States
Heather G.
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..

Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!

Rushville
9.6 out of 10, Exceptional, (65)
"Beautiful property with wonderful amenities. Very comfortable and spacious. We loved every minute of it. "
United States
Mary Kay M.
Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!

Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.

Branchport
10.0 out of 10, Exceptional, (273)
"It was nice quiet location place was very clean and well maintained check in was very easy we will definitely stay again if opportunity arises "
United States
Rod S.
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.

Naples Valley Getaway-Private home with hot tub.

Naples
10.0 out of 10, Exceptional, (352)
"Cabin was extremely clean, well-stocked with the essentials, and cozy. Lovely place to stay at for our trip to the Finger Lakes. Hot tub was relaxing and our son really enjoyed the cornhole set. Highly recommend! "
United States
Laura D.
Naples Valley Getaway-Private home with hot tub.

Sandy Beach Haven - Modern Canandaigua Lake House

Canandaigua
10.0 out of 10, Exceptional, (119)
"Loved this house. The two master suites were awesome. Great views and great location. "
United States
Lisa S.
Sandy Beach Haven - Modern Canandaigua Lake House

Lakefront gem with game room and dock - the house that almost floated away

Penn Yan
9.2 out of 10, Wonderful, (60)
"Very nice, clean, the finished basement is awesome! Close to wineries and Penn Yan. I highly recommend the property."
United States
Michael
Lakefront gem with game room and dock - the house that almost floated away

Lakeside Home, New Pool, Carriage House, level & private, 6 BR, 120' frontage!

Canandaigua
10.0 out of 10, Exceptional, (115)
"Great place for family"
United States
Amy M.
Lakeside Home, New Pool, Carriage House, level & private, 6 BR, 120' frontage!

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)
"Property was exactly as described and the view was spectacular! Host Maryanne was extremely helpful & kind, and we would be delighted to stay at this property again in the future. "
United States
Sydney W.
$267 nightly
The price is $298
Nov 11 - Nov 12
Total with taxes and fees
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!

Romantic Cabin On-the-Water Breathtaking View Beach Fire Pit! Jul'26 1 Wk Avail

Hammondsport
9.2 out of 10, Wonderful, (188)
"Location is great. Owner is very nice. Wish the property was kept up a bit nicer. Overall it was a great place to stay."
United States
Wanzhu F.
Romantic Cabin On-the-Water Breathtaking View Beach Fire Pit! Jul'26 1 Wk Avail

Wildflower-Seneca Lake-Water View-Hot Tub-Wine Trail - Pets, Steps to Lake-Acre of Privacy

Dresden
8.6 out of 10, Excellent, (104)
"The property was clean, and very convenient to all that we wanted to do. We did not use the hot tub as we weren't interested in that. Overall a great week's stay. Pics of the lake views on the site need updating to reflect actual views. It was my only disappointment as it was a factor in selecting this rental. "
United States
p r.
Wildflower-Seneca Lake-Water View-Hot Tub-Wine Trail - Pets, Steps to Lake-Acre of Privacy

Finger Lakes Mission House Family Retreat

Conesus
9.4 out of 10, Exceptional, (97)
"This place was fantastic. Kory was accommodating to special needs. Friends and family that came in for our daughter's wedding enjoyed their stay and loved the view and amenities that was offered."
United States
Bruce R.
Finger Lakes Mission House Family Retreat

Serenity Zen House on Seneca Lake - Pet Friendly

Penn Yan
9.8 out of 10, Exceptional, (178)
"Nice location and fun times"
United States
RICHARD B.
Serenity Zen House on Seneca Lake - Pet Friendly

THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!

Hammondsport
9.8 out of 10, Exceptional, (60)
"We thoroughly enjoyed our stay at this quaint off the grid with an amazing view. The new shower "house" is adorable. Joann and Dave were very nice. "
United States
Lori F.
THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!

Sunflower-Keuka/Seneca-Lake View-Hot Tub-Wine Trail-Pets, 13 Wooded Acres-7 min to Beach

Barrington
9.6 out of 10, Exceptional, (97)
"This is our second trip to Sunflower Cottage and the location is perfect. Near wineries, markets and the lake, this charming cottage has turned into our go-to spot for a fall getaway!!"
United States
KAREN C.
Sunflower-Keuka/Seneca-Lake View-Hot Tub-Wine Trail-Pets, 13 Wooded Acres-7 min to Beach

Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch

Dundee
9.2 out of 10, Wonderful, (106)
"Enjoyed the location and large house, there was plenty of room for everyone."
United States
Diane S.
Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch

Cottage on active vineyard with lovely views, grill, firepit, EV charger, & W/D

Keuka Park
9.8 out of 10, Exceptional, (16)
"Such a beautiful house and view! I can't wait to stay again. "
United States
Christina R.
Cottage on active vineyard with lovely views, grill, firepit, EV charger, & W/D

Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI

Penn Yan
9.8 out of 10, Exceptional, (251)
"We loved the place. It was perfect for a long weekend. The driveway is steep, but we parked along the road and it was fine. Great place. "
United States
Wade A.
Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI

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

Penn Yan
9.8 out of 10, Exceptional, (150)
"loved our short stay. Was nice to come back and play badminton. Enjoyed our days at Keuka lake state park."
United States
Tina g.
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

FROG HOUSE - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! 4 Seasons

2.0 star property
Prattsburgh
9.2 out of 10, Wonderful, (14)
"Overall, our impression is that the property was very comfortable as a campsite. The property was very much what we had hoped for -- (mostly) quiet, forest, trails. Thought "Frog House" meant frog sounds all night, but .... "
United States
Joseph C.
FROG HOUSE - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! 4 Seasons
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesex vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middlesex in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $193 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex vacation 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 vacation.

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 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?

Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!: This vacation home rental outside of Middlesex is located on a lake and has a balcony, an arcade game room, and a barbecue grill 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 you can cook with friends or family.

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.