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Compare 435 Vacation Homes in Middlesex with updated reviews, rates, and availability.

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

9.4 out of 10, Exceptional, (53)
"Thank you for sharing your beautiful home with our party. Enjoyed our time, all amenities were as described in listing. Would return in the future."
Lakefront gem with game room and dock - the house that almost floated away

Fall Brook: Modern, woodsy home beside waterfalls and hiking trails

10.0 out of 10, Exceptional, (12)
"Had everything we needed. Pots, Pans, Spices, etc. and located on a great hiking trail."
Fall Brook: Modern, woodsy home beside waterfalls and hiking trails

Charming Canandaigua Lake House w/ Deck & Views!

10.0 out of 10, Exceptional, (19)
"Wonderful house, nice & quiet, beautiful views. "
Charming Canandaigua Lake House w/ Deck & Views!

Large Lakeview Lodge on Canandaigua Lake

9.6 out of 10, Exceptional, (59)
"Family reunion, we rented a boat, excellent accommodations !"
Large Lakeview Lodge on Canandaigua Lake

Cedar Lane Cabin: Authentic log cabin in wooded setting overlooking rural farmland

9.4 out of 10, Exceptional, (46)
"We so enjoyed our stay, especially given there were no near barking dogs or misbehaving children (we are empty nesters). The property though, needs to have the addition of a TV and DVD movie selections. We brought a portable DVD player with us. This could be easily added to the lower level room. There were a number of items that needed repair, but did not interfere with our stay. The intensity of "house rules" being frequently deluvered via text and email, felt overwhelming and somewhat...
Cedar Lane Cabin: Authentic log cabin in wooded setting overlooking rural farmland

Best Value on Seneca Lake! RARE Level Lakefront on the Wine Trail!

10.0 out of 10, Exceptional, (73)
"Two families of 4 from Canada met up and we had a great time. The house accommodated all 8 of us very well. Both for sleeping, eating and game nights. The location on the water was stunning. Must be wonderful to go for a swim in the summer. Water a bit too cold in December. Overall a great experience. We can see ourselves coming back here. "
Best Value on Seneca Lake! RARE Level Lakefront on the Wine Trail!

Secluded home with large deck, foosball table, & W/D - near skiing

8.4 out of 10, Very Good, (6)
"Great"
Secluded home with large deck, foosball table, & W/D - near skiing

Penn Yan House Rental - Close to Wineries!

9.6 out of 10, Exceptional, (4)
"This was a lovely little home for our weekend getaway. It is walking distance to multiple restaurants and shops in Penn Yann and the owner's were kind enough to recommend wineries for us."
Penn Yan House Rental - Close to Wineries!

Stunning 4-bedroom house with AC and WiFi in the quaint town of Hammondsport

Stunning 4-bedroom house with AC and WiFi in the quaint town of Hammondsport

Retreat of falling waters

9.0 out of 10, Wonderful, (199)
"I’ve been staying here every time I need to get away. It’s better than the pictures show. I highly recommend."
Retreat of falling waters

Pet-Friendly Ovid Home Near Seneca Lake & Wineries

9.0 out of 10, Wonderful, (31)
"The property was adequate for our needs and we did enjoy our time there together with our family from Canada and it's a convenient location to hit the wineries and breweries in the area. However, even though the house is cute, it is in need of a deep cleaning as the windows and screens were dirty, the stove was greasy and the floors need scrubbing. There's really not enough kitchen equipment to be able to properly cook meals. Like, pots, pans, plates, silverware, utensils. You couldn't have the...
Pet-Friendly Ovid Home Near Seneca Lake & Wineries

Classic country retreat with a game room, bar, expansive outdoor space, & grill

8.8 out of 10, Excellent, (8)
"The family gathered for Christmas/New Years and had plenty of room for puzzles, games and watching tv. Close to activities and sites. Enjoyed the area and quiet country. "
Classic country retreat with a game room, bar, expansive outdoor space, & grill

Chalet: modern cozy cabin on Seneca lake wine trail with outdoor firepit

10.0 out of 10, Exceptional, (34)
"Very clean, sparse amenities, kitchen could use updated towels, potholders had to buy a scrubber to clean stainless steel pans Neighbors facing property across the street not shown in pictures, no access to lake from property. All privately owned."
Chalet: modern cozy cabin on Seneca lake wine trail with outdoor firepit

Arrowhead Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Pets, Recently Updated-Covered Deck

9.2 out of 10, Wonderful, (204)
"Highly recommend. We enjoyed the remote location right on the lake. "
Arrowhead Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Pets, Recently Updated-Covered Deck

Wine and Dine Haven: Luxury Rental with Stunning Views of Keuka Lake

10.0 out of 10, Exceptional, (59)
"Great spot. Took six girl friends for a mom’s weekend off. This house has everything and more! Fire pit, hot tub, deck with amazing views, games and everything you could want in a kitchen. We had coffee and wine on repeat. Would be a great spot in warm months but we enjoyed toasty fireplaces and several sitting areas to hang out and unwind. Did wine tour of the lake and was gorgeous. Margaret was responsive and wonderful. We can’t wait to come back!"
Wine and Dine Haven: Luxury Rental with Stunning Views of Keuka Lake

Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.

10.0 out of 10, Exceptional, (23)
"Comfortable home, lots of character. Close to downtown and HWS. Perfect for our weekend stay. Owner were extremely helpful and available."
Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.

Among the Oaks: Newly built Luxury home with game room, wooded setting overlooking Seneca lake

10.0 out of 10, Exceptional, (5)
"We stayed over the weekend for the deck the halls event. Property was excellent and we would definitely stay again. I have no complaints."
Among the Oaks: Newly built Luxury home with game room, wooded setting overlooking Seneca lake

Call of the Bluff: Pet friendly, rural home with amazing views of Keuka Lake!

9.6 out of 10, Exceptional, (31)
"The view was fabulous, as was the outdoor living space. The property is not well suited for 2 couples with one bath upstairs with bedrooms and the other bath on the main level. The kitchen was great, well stocked but the sink was pretty disgusting. Nothing that a little Soft Scrub with bleach or Mr Eraser wouldn’t take care of. All in all a nice property, just better suited for a family with kids. "
Call of the Bluff: Pet friendly, rural home with amazing views of Keuka Lake!

Castello: modern cabin with hot tub, pool table and Seneca lake view, along wine trail

10.0 out of 10, Exceptional, (81)
"Perfect location for our wine tour. House and hot tub were very clean. Fireplaces work great for heat. Overall amazing property "
Castello: modern cabin with hot tub, pool table and Seneca lake view, along wine trail

Cozy Bungalow

10.0 out of 10, Exceptional, (3)
"Very cute and very clean little bungalow get away. Close to finger lakes for wine touring. Quit nice neighborhood and a cute outside deck with a bar style table to set outside and enjoy the evening. Will definitely stay again."
Cozy Bungalow
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, (197)
"This property was exactly how it was described! Nestled in the hills, super cozy, and welcoming feeling. My partner, pups and I had a lovely time here, hiking, skiing at Bristol Mountain Resort, and enjoying the serene landscape, especially the surprise waterfall in the backyard! The hot tub was an amazing bonus after a long day of skiing. Perfect way to ring in the New Year! We will definitely be back! "
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.