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Compare 135 Cottages in Middlesex with updated reviews, rates, and availability.

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

8.8 out of 10, Excellent, (198)
"Perfect little getaway with the hot tub and a cozy and quiet hill. Glad we had the four-wheel-drive car to get up the hill!!!"
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..

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

9.8 out of 10, Exceptional, (253)
"The location of the Vrbo was perfect. We were going to an event called Deck the Halls at Seneca Lake in the Finger Lakes region. Vrbo was clean, quaint and quiet. A beautiful view of Seneca Lake. We all had a great time!"
Cozy new England style cottage Right on Wine and Beer Trail

Amish Built Cottage near Fingerlakes Wineries, Fishing, Hiking, Hunting & More!

10.0 out of 10, Exceptional, (36)
"Great location and price Very clean already hope to rent again"
Amish Built Cottage near Fingerlakes Wineries, Fishing, Hiking, Hunting & More!

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

3.0 star property
9.8 out of 10, Exceptional, (48)
"We had a nice time at Maryann's property last week. The location was great and was in the middle of many great wineries, restaurants, and towns. The cottage was clean and it was beautiful to wake up on the lake! The sunrises were incredible!"
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!

The Heart Of The Wine Country! Sip wine, take a dip, relax and enjoy

9.8 out of 10, Exceptional, (155)
"Located at the end of a dirt road along the lake, this cozy home leaves little to be desired. It’s off the beaten path and provides seclusion as well close proximity to the wide variety of wineries and towns in the area. The host was wonderful; calling before our arrival to ensure there were no questions, and informing us of a temporary power outage the day we were to arrive. The home was well kept, fully stocked, and clean upon our arrival. The Finger Lakes is one of my favorite vacation...
The Heart Of The Wine Country! Sip wine, take a dip, relax and enjoy

Beautiful Views, Sunrises, Pet Friendly, Comfortable!

10.0 out of 10, Exceptional, (101)
"Our stay was everything we expected and more. The house was well stocked with everything we needed and more!!! "
Beautiful Views, Sunrises, Pet Friendly, Comfortable!

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

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

HUGE DECK! ENJOY the beauty and quaintness of this 3 bedroom and 2 bath cottage

10.0 out of 10, Exceptional, (32)
"We had a great time! Amazing deck! Beautiful location. The only thing I would warn folks about is the steepness of the stairs to the property - there are a lot of stairs and they are pretty steep. "
HUGE DECK! ENJOY the beauty and quaintness of this 3 bedroom and 2 bath cottage

Pet-friendly Honeoye Cottage Rental: Walk to Lake!

3.0 star property
6.0 out of 10, (2)
"The owners have thought of everything. There were even snacks on the counter when we arrived. We had a very relaxing stay and would definitely stay again."
Pet-friendly Honeoye Cottage Rental: Walk to Lake!

Sip, Splash, and Relax at Caywood Cottage - a peaceful wine country retreat!

9.6 out of 10, Exceptional, (61)
"It was a Beautiful peaceful place, Clean, great views. No issues to speak of. Would stay again. "
Sip, Splash, and Relax at Caywood Cottage - a peaceful wine country retreat!

Hot Tub, Lake View Cottage, Dog Friendly, Lake Access

10.0 out of 10, Exceptional, (14)
"Great place for a weekend get away! It’s beautiful, very clean and welcoming! The fire pit and hot tub were wonderful after a day of hiking. Very close to wineries and great restaurants! "
Hot Tub, Lake View Cottage, Dog Friendly, Lake Access

Beautiful Waneta Lake Front Cottage! KAYAKS! Wine Country FLX

9.6 out of 10, Exceptional, (15)
"We enjoyed the quiet and cozy stay at this place. It's tucked away enough from the towns but still within 20 minutes of most attractions."
Beautiful Waneta Lake Front Cottage! KAYAKS! Wine Country FLX

Finger Lakes Cottage Getaway

10.0 out of 10, Exceptional, (34)
"This property was amazing! My husband and I spent our honeymoon here exploring the fingerlakes and this cottage was an amazing place to stay and relax between adventures! The views were spectacular!"
Finger Lakes Cottage Getaway

Keuka Lake | Panoramic Lake Views | Lake Access

8.2 out of 10, Very Good, (11)
"Overall this is a great place to stay, heat is a bit weak in the fall. No unit in 3rd floor bedrooms made them a little chilly"
Keuka Lake | Panoramic Lake Views | Lake Access

Finger Lakes Cottage

10.0 out of 10, Exceptional, (77)
"This is our third year and have never been disappointed. Plan to return next year. Bob is very quick with answering questions and great host"
Finger Lakes Cottage

Waterfront Cottage on Keuka Lake near Penn Yan

9.8 out of 10, Exceptional, (28)
"We had an amazing bachelorette weekend for a soon to be bride! The rental gave a perfect cottagey vibe with cute decorations and beautiful lakeside views. We enjoyed all sitting around the large dining room table and using the fire pit on the patio, as well as cooking on the grill for dinner! My only suggestion would be to include at least one full length mirror in the main house, and designated hampers for used towels. We had so much fun and really hope to visit again!!"
Waterfront Cottage on Keuka Lake near Penn Yan

Calming lakefront home with firepit, kitchen, kayaks, grill, patio & hammock

8.8 out of 10, Excellent, (18)
"Loved the location and private access to the lake. Sunrises on the porch with coffee were unforgettable. 1950s charm with modern amenities, can’t beat it. Loved the original front door and rotary phone, a step back in time. Steps not a problem, just a little extra exercise. Clean and comfy. Only notes would be to replace the couch (seems well loved) and address the subfloor in the bathroom by the shower, but not deal breakers. Will stay again! "
Calming lakefront home with firepit, kitchen, kayaks, grill, patio & hammock

While Away Cottage

10.0 out of 10, Exceptional, (90)
"2 couples, stayed there in mid November. House inside and out is practically brand new. Kitchen is well stocked, plenty of towels and linens. It was cold while we were there, but the outside deck is very large and spacious. Grill could use some help, and there are no TVs. Basement is a plus, but we didn't use it. Property manager lives right across the street and greeted us when we arrived to make sure everything was in order. When we come to the finger lakes, we will rent this house again."
While Away Cottage
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

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

8.8 out of 10, Excellent, (198)
"Perfect little getaway with the hot tub and a cozy and quiet hill. Glad we had the four-wheel-drive car to get up the hill!!!"
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..

WELCOME! WE ARE PET FRIENDLY.

9.8 out of 10, Exceptional, (263)
"My husband and I enjoyed our 3 night visit to Grouse Haven. It was extremely peaceful and relaxing. The surrounding area was beautiful and we enjoyed walking in the snow covered woods on the property. We enjoyed our time at Grouse Haven so much that we hated to leave. Phyllis was a delight to get to know and was very helpful to us. We can’t wait to make a return visit to this lovely property."
WELCOME! WE ARE PET FRIENDLY.

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

9.8 out of 10, Exceptional, (46)
"My girlfriend and I had a great glamping experience hosted by Dave and his wife. Not only was Dave incredibly attentive during our stay but also gave us recommendations on where to explore around the town and hikes near by. The cabin was equipped with cooking material and wood for the fire (which we really enioyed). For anyone looking for sometime to disconnect and enjoy with a loved one - We recommend this cabin for you!"
THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!
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!
How can I find cheap cottages in Middlesex?
Expedia can help you look for cheap cottages in Middlesex. To lock in your dream stay in a few quick clicks, simply use our handy filter tool to tailor your search results by budget, amenities and star rating.