Photo by Matthew Jay

Search Vacation Homes in Middlesex

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 610 Vacation Homes in Middlesex with updated reviews, rates, and availability.

Lakefront Home in the heart of Seneca Lake Wine Trail

9.8 out of 10, Exceptional, (48)
"We had a lovely stay there. Everything was as described and is beautiful set right against the lake. Perfect location for Seneca or Keuka lake wineries. "
Lakefront Home in the heart of Seneca Lake Wine Trail

Retreat of falling waters

9.0 out of 10, Wonderful, (203)
"Our stay at the Retreat of Falling Waters was nothing short of magical. We loved exploring the waterfall, playing the board games provided, and enjoying meals at the quaint kitchen table. Just plan to bring your own drinking water because the well water connected to the property isn’t really safe to drink! Thank you so much to the incredibly communicative host! "
Retreat of falling waters

Naples Valley Getaway! Private home with hot tub.

10.0 out of 10, Exceptional, (322)
"A very well kept beautiful cabin in the woods! We really enjoyed staying in this cabin and the Naples area has so many things to do and see."
Naples Valley Getaway! Private home with hot tub.

Peaceful, pet friendly and newly remodeled Geneva home

9.6 out of 10, Exceptional, (10)
"My husband and I, along with my parents visited my daughter at HWS. Our stay was very comfortable. The owner had made sure to have lights on as we were arriving after dark. "
The price is AED 643
AED 1,080 total
includes taxes & fees
29 Apr - 30 Apr
Peaceful, pet friendly and newly remodeled Geneva home

Charming Canandaigua Lake House w/ Deck & Views!

9.8 out of 10, Exceptional, (20)
"Simple, clean and wonderful spot for a winter weekend getaway."
Charming Canandaigua Lake House w/ Deck & Views!

Croft Cove: laid back home on Lamoka Lake with private lakefront

9.6 out of 10, Exceptional, (33)
"This house is such a gem. From the comfort of the beds to the view of the lake, everything was just wonderful. I would love to stay here again."
Croft Cove: laid back home on Lamoka Lake with private lakefront

Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK

9.2 out of 10, Wonderful, (292)
"We stayed here a few years ago and loved it. This visit was the same. Great location mid-way between Watkins Glen and Geneva. Eclectically decorated and very nicely maintained. Kitchen is well equipped. Strong wifi. Beautiful view looking east over the lake. Watching the sunrise is a must!! "
Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK

Plum Point Villa - Stunning View In The Heart Of The Finger Lakes!

9.8 out of 10, Exceptional, (154)
"We had a great ladies weekend ! Beautiful lake view and plenty of room for our group "
Plum Point Villa - Stunning View In The Heart Of The Finger Lakes!

Townhouse with Lake views/access, 10 min to ski Bristol Mountain

9.8 out of 10, Exceptional, (51)
" Leyla’s place is all that’s advertised and more. Its three levels, its high ceilings give you plenty of room to stretch out and relax. Everything is provided for a comfortable, even luxurious, stay for any length.. The view of the lake is picture postcard worthy. With a touch of wild. On the two mornings we were there we saw deer grazing in the woods bordering the backyard lawn. And in one scintillating moment my wife spotted a red fox streaking through the grass.Leyla is an attentive host,...
Townhouse with Lake views/access, 10 min to ski Bristol Mountain

Direct Waterfront private house, NEW 40ft dock w/power, sleeps 8 in Wine Country

10.0 out of 10, Exceptional, (30)
"The house was extremely clean and well taken care of. Attention to all the small details really made it feel like home. We would definitely stay again! Host was great! Highly recommend the property "
Direct Waterfront private house, NEW 40ft dock w/power, sleeps 8 in Wine Country

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

10.0 out of 10, Exceptional, (6)
"Stayed with friends for a long weekend and everything about the property was perfect. "
Among the Oaks: Newly built Luxury home with game room, wooded setting overlooking Seneca lake

TreeTops, modern luxury overlooking Keuka Lake - luxury Treehouse new for 2025!

9.8 out of 10, Exceptional, (8)
"We thoroughly enjoyed staying at TreeTops! The property is beautiful, clean and has an awesome view. We would stay again without hesitation!"
TreeTops, modern luxury overlooking Keuka Lake - luxury Treehouse new for 2025!

Spacious ‘GEM’ of the city

9.8 out of 10, Exceptional, (30)
"House was well stocked and clean. House was walkable to all restaurants and shops. Easy drive to many wineries. The beds were very comfortable and plenty of towels for the group. "
The price is AED 911
AED 1,502 total
includes taxes & fees
5 May - 6 May
Spacious ‘GEM’ of the city

The village of Keuka

9.4 out of 10, Exceptional, (45)
"Everything about the property was wonderful"
The village of Keuka

Awesome On-the-Water Romantic Cottage w/Breathtaking Views and Beach Fire Pit!

9.2 out of 10, Wonderful, (176)
"OMG!!! This place is absolutely BEAUTIFUL! Right on the water, absolutely perfect! The property manager is incredibly helpful and readily available for any questions! The cottage was immaculate! The location is also perfect! Will definitely be returning to this cottage! We had a phenomenal time! Simply amazing!"
Awesome On-the-Water Romantic Cottage w/Breathtaking Views and Beach Fire Pit!

The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK

9.8 out of 10, Exceptional, (37)
"Beautifully decorated farm house with hot tub was the perfect place to relax after visiting the area state parks. We highly recommend this home. Thanks for an enjoyable stay!!"
The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK

Pet-Friendly Seneca Lake Home w/ Private Deck

9.4 out of 10, Exceptional, (32)
"This place is as listed and shown in pictures. It’s a great location when doing a wine tour. My friends and I had a weekend visit for a wine tour and found the location convenient. We were close to wineries and BBQ’s. Yum! I would just make a note that there is no tv (if you want to watch any). This is also an old farm house and you may have some unexpected guests There were tiny ants on the counter and sink (we cleaned them up with kitchen cleaner) and we suggest keeping food in the...
Pet-Friendly Seneca Lake Home w/ Private Deck

Spacious home with private lake front

8.8 out of 10, Excellent, (5)
"We had a great stay. The check in process was easy. The property was large and had everything we needed. It was an easy walk across the road to get to the dock and waterfront. It was the perfect getaway while visiting family and friends in the Rochester, NY area. German Brothers Marina is just a little ways down the road and we rented a boat one day and it was easy to stop at the dock and exchange passengers. The dock also worked out well for swimming and fishing. The driveway was large...
Spacious home with private lake front

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

9.8 out of 10, Exceptional, (35)
"We have been visiting the finger lakes region for many years and have recently gotten on board with the Air B&B/VRBO trend. This was the second rental we stayed in this year and we will definitely be back. Central location on the west side of the Seneca lake wine trail, 15-20 minutes to both Watkins Glen and Geneva. Also a quick trip to Keuka lake. The home was clean, bright and the rooms were tastefully decorated, which is a nice bonus. High ceilings made it feel even more spacious. Absolutely...
Chalet: modern cozy cabin on Seneca lake wine trail with outdoor firepit

Moon Dance: lake home on Seneca Lake with private beachfront

9.8 out of 10, Exceptional, (27)
"We are a group of retired friends on a Wine Trip. There were 9 of us. The home was the perfect size. When we encountered some minor issues, they were addressed immediately. I highly recommend and look forward to returning again when the weather allows to be on the deck "
Moon Dance: lake home on Seneca Lake with private beachfront
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.
Don't see what you're looking for?
See all available properties in Middlesex
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middlesex

Woodcliff Hotel and Spa

4.0 star property
8.6 out of 10, Excellent, (1007)
"I like the proximity to my home office (employer) right across the street when I travel. What I don’t like about the property is that the hotel is in an old building and the rooms are not kept up for a hotel that tends to cater to working traveling professionals. Halls are musty and smelly at times. Shower door removed from bathroom as part of ‘remodel’ - replaced by shower curtain full of orange mold at bottom. Pros: always a comfortable sleep. Free Starbucks cup of coffee. Staff is always...
The price is AED 559
AED 696 total
includes taxes & fees
28 Apr - 29 Apr
Woodcliff Hotel and Spa

del Lago Resort & Casino

4.0 star property
9.2 out of 10, Wonderful, (1429)
"Overall, it was a wonderful two-night stay. The only sad aspect was that the hotel did not offer a guest laundry room."
The price is AED 434
AED 482 total
includes taxes & fees
28 Apr - 29 Apr
del Lago Resort & Casino

Holiday Inn Hotel & Suites Rochester - Marketplace by IHG

3.0 star property
8.0 out of 10, Very Good, (1005)
"Very friendly and overall good experience. We picked the hotel because it had an EV car charger and a bar. The EV charger worked well, but we were disappointed that the bar was closed when we arrived at 9:30 even though it was supposed to be open until 10. "
The price is AED 444
AED 507 total
includes taxes & fees
30 Apr - 1 May
Holiday Inn Hotel & Suites Rochester - Marketplace by IHG
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.