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Compare 132 Cottages in Middlesex with updated reviews, rates, and availability.

1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!
Outdoor dining
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!
3.0 star property
9.8 out of 10, Exceptional, (38)
"I enjoyed my stay. The cottage is lovely, charming. Maryanne is just a lovely host. I had questions for her and she responded pretty quickly. The views of the lake, sunsets, sunrises, moon is breathtaking. "
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..
Exterior
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..
8.6 out of 10, Excellent, (181)
"I had trouble with the lock box until we realized it was not going to unlock-that you open it to get the key lol. Pleasantly surprised at the cute cottage, very clean and everything you need. We brought our own water and coffee pot as it was only 2 of us and I am used to my tiny 2 cup cone filtered coffee. The Atari machine was fun. My dog enjoyed doing loops around the place and going down to the fishing dock. Not a long drive to the artsy 5th most laid back town in NYS Naples where everyone...
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..
Calming lakefront home with firepit, kitchen, kayaks, grill, patio & hammock
Calming lakefront home with firepit, kitchen, kayaks, grill, patio & hammock
8.6 out of 10, Excellent, (12)
"Terrible!"
Calming lakefront home with firepit, kitchen, kayaks, grill, patio & hammock
Quiet Cozy Cottage on Keuka Lake Wine Trail
Terrace/patio
Quiet Cozy Cottage on Keuka Lake Wine Trail
9.8 out of 10, Exceptional, (71)
"House was everything that we expected and more!! Beautiful lakefront property!"
Quiet Cozy Cottage on Keuka Lake Wine Trail
Junius Pond
Exterior
Junius Pond
3.0 star property
2.0 out of 10, (1)
"not a comfortable environment at all, cabin was full of bugs and cob webs everywhere, have to pay for guest’s to come visit. They say speed limit 5 mph but they zoom around on go carts going past cars, then tell the cars to slow down, because you’re not white!!!!!!! Most horrible experience ever!!! Then got police called on us as well!!!!! "
Junius Pond
Finger Lakes Cottage
Exterior
Finger Lakes Cottage
10.0 out of 10, Exceptional, (73)
"Beautiful property, inside and out. Felt like ‘home away from home’ right away. Loved the porches. Well-stocked with essentials. Very neat, clean and uncluttered. Located fairly close to anything you’d be interested in exploring. Definitely well worth the visit."
Finger Lakes Cottage
While Away Cottage
While Away Cottage
While Away Cottage
10.0 out of 10, Exceptional, (84)
"Our stay was amazing. The place was newer, immaculate, and so cozy. The coffee bar was great. We spent lot of time on the patio enjoying the peace and quiet and taking in the backyard. Although we don’t have small children the finished playroom in the basement was adorable, and the air hockey and pool table was fun for us adults. It was the perfect place for a family vacation. "
While Away Cottage
Stone's Throw from Keuka College
Living area
Stone's Throw from Keuka College
10.0 out of 10, Exceptional, (20)
"We had a wonderful time exploring Keuka Lake! “Stone's Throw” was the perfect spot to come home to! We liked it so much that we booked for next year! The hosts were attentive and have thought of everything for this wonderful little house!"
Stone's Throw from Keuka College
Canandaigua Lake Cottage
Dining Area
Canandaigua Lake Cottage
10.0 out of 10, Exceptional, (9)
"Came to town to see a concert at CMAC. Perfect place to stay, short drive or Uber ride away. Wish we had stayed longer to explore the area more. I would definitely stay again."
Canandaigua Lake Cottage
Canandaigua Lakefront Gem w/ Dock & Boat Slip
Middlesex Vacation Rental | 3BR | 1BA | 1,180 Sq Ft | Steps Required
Canandaigua Lakefront Gem w/ Dock & Boat Slip
Canandaigua Lakefront Gem w/ Dock & Boat Slip
Cozy new England style cottage Right on Wine and Beer Trail
Sun Rise
Cozy new England style cottage Right on Wine and Beer Trail
9.8 out of 10, Exceptional, (248)
"Wonderful charming cottage with a fantastic location to all of the wineries!!"
Cozy new England style cottage Right on Wine and Beer Trail
Hot Tub, Lake View Cottage, Dog Friendly, Lake Access
Property grounds
Hot Tub, Lake View Cottage, Dog Friendly, Lake Access
10.0 out of 10, Exceptional, (13)
"The Hosts are wonderful, they make you feel at home, accommodating, very kind, the home is very clean and even offered extras-definitely would rent again "
Hot Tub, Lake View Cottage, Dog Friendly, Lake Access
Keuka Lake | Panoramic Lake Views | Lake Access
Listen to the waves crash as you relax in the hammock and finally take that nap you have been promising yourself
Keuka Lake | Panoramic Lake Views | Lake Access
8.8 out of 10, Excellent, (8)
"Very nice stay at the lake. House was clean and as advertised. It was perfect having morning coffee out on the deck and the family enjoyed kayaking and swimming in the lake. Switzerland Inn and Olney's Place are both super close and good spots to eat! "
Keuka Lake | Panoramic Lake Views | Lake Access
Beautiful Views, Sunrises, Pet Friendly, Comfortable!
Outdoor dining
Beautiful Views, Sunrises, Pet Friendly, Comfortable!
10.0 out of 10, Exceptional, (91)
"Great place to stay! We did some hiking in the day and checked out local wineries. Place was well outfitted with dock and kayaks plus much more! "
Beautiful Views, Sunrises, Pet Friendly, Comfortable!
Cozy Lake Front Cottage
Exterior
Cozy Lake Front Cottage
9.8 out of 10, Exceptional, (19)
"Beautiful property! Easy access. Nicely decorated and fully stocked with amenities. However, due to the awkward layout, we would have been much more comfortable with privacy window treatments in the front porch area. Also, the shower floor is EXTREMELY slippery. We would definitely rent again. Hopefully with those 2 issues addressed. Thank you so much for sharing your lovely cottage with us!"
Cozy Lake Front Cottage
Fall in love with Keuka at Keuka Kara
Lakeside view of Keuka Kara
Fall in love with Keuka at Keuka Kara
9.8 out of 10, Exceptional, (73)
"Our family of 12 stayed for a week and had a wonderful visit. All the bedrooms accommodated us well and the gathering space on the main floor allowed for us all to eat meals and spend time together. The owner was very responsive to all of our questions and the house was very clean upon our arrival. The location can't be beat. We docked our boat for the week and it was a very sturdy, well cared for dock. Would love to stay again!"
Fall in love with Keuka at Keuka Kara
Lakefront Canandaigua Home w/ Grill, Fire Pit
Canandaigua Vacation Rental | 2BR | 1BA | 1,000 Sq Ft | Steps Required
Lakefront Canandaigua Home w/ Grill, Fire Pit
9.8 out of 10, Exceptional, (18)
"My second time here. Ideal location to enjoy the sunrise and sunset. First time visiting the mansion and grounds of the Sonnenberg Gardens. I would love to come back!? "
Lakefront Canandaigua Home w/ Grill, Fire Pit
Pet-friendly Ovid Home Near Seneca Lake & Wineries
Terrace/patio
Pet-friendly Ovid Home Near Seneca Lake & Wineries
3.0 star property
10.0 out of 10, Exceptional, (1)
Pet-friendly Ovid Home Near Seneca Lake & Wineries
Cozy Keuka cottage - 3 steps away from the lake!
Sunbathing & Swim Dock
Cozy Keuka cottage - 3 steps away from the lake!
9.8 out of 10, Exceptional, (16)
"Love this house! We are return renters and the changes the new owners, Tom and Jess, made are great. The new dock with the lounge chairs is worth getting this house. I read in the sunshine during day then switched to the beach to wade and swim. Then we watched the sunset and gazed at the stars every night from the dock. Views are phenomenal from this house! We were going to use the kayaks but never did but they are there. Kitchen has what you need to barbecue and cook. House clean, beds...
Cozy Keuka cottage - 3 steps away from the lake!
WOW! Newly Renovated Cottage on Keuka Lake. Perfect for a Vacation on the Water
Aerial view
WOW! Newly Renovated Cottage on Keuka Lake. Perfect for a Vacation on the Water
10.0 out of 10, Exceptional, (6)
"This was by far the cleanest, most up-to-date home we have stayed in at Keuka Lake. The new renovations are so well done and the house was well-stocked with everything you could possibly need. We stayed with our family (raging in ages of 2 months up to 65 years) and there were fun activities for everyone. We especially enjoyed the beach area for the kids to play, the fire pit, the kayaks and paddle board, and the beautiful dock. The host was responsive and helpful. Thank you for a wonderful...
WOW! Newly Renovated Cottage on Keuka Lake. Perfect for a Vacation on the Water
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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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Other property types in Middlesex

THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!
THE GRAPE ESCAPE
THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!
9.8 out of 10, Exceptional, (42)
"We had the best long weekend staying at the Grape Escape. Highly recommended! "
THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!
Retreat of falling waters
Exterior
Retreat of falling waters
9.0 out of 10, Wonderful, (191)
"2 couples on a quick get away. Looking to enjoy Canandaigua lake, wineries, and breweries. Also wanted an outdoorsy space. sit by the fire "
Retreat of falling waters
Cozy Bungalow right on the Lake wine and brewery trail.
SUN RISE
Cozy Bungalow right on the Lake wine and brewery trail.
9.4 out of 10, Exceptional, (20)
"The cute little bungalow is right on the water. Well, put together, everything you need. With friendly neighbors. The sunrise and Sunset is beautiful. When I go back to the area, I will be staying there again. "
The price is SAR 563
SAR 998 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Bungalow right on the Lake wine and brewery trail.
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.

Frequently asked questions

How much do cottages in Middlesex cost?
Cottages in Middlesex range between and per night. These retreats offer a chance to touch base with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Middlesex with Expedia?
Booking a cottage in Middlesex is as simple as entering your travel dates and choosing an ideal place for outdoor fun and relaxation. From high-end retreats to budget-friendly properties and cottages that offer perks like a pool, Expedia has something for all tastes. As for awesome deals? We’ve got them as well!
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