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Search Vacation Homes in Middlesex

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Compare 436 Vacation Homes in Middlesex with updated reviews, rates, and availability.

Retreat of falling waters

9.0 out of 10, Wonderful, (196)
"Cozy. The hot tub was great after a day of walking the many trails in the area"
Retreat of falling waters

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

creek's edge

9.8 out of 10, Exceptional, (18)
"Stayed for the night after going to a concert, amazing place felt very safe there and had no concerns!"
The price is AED 364
AED 437 total
includes taxes & fees
21 Dec - 22 Dec
creek's edge

Naples Private home with hot tub. Discounts on select December dates available

10.0 out of 10, Exceptional, (304)
"Such a cute house and property! We highly enjoyed our stay!! The house was amazing and the hotub was so clean and relaxing!! Love that it is just a couple miles from a few wineries and town. We will be coming back!"
Naples Private home with hot tub. Discounts on select December dates available

Cozy Chateau cabin with hot tub, pool table, and view of Seneca Lake, close to Wine trail

10.0 out of 10, Exceptional, (87)
"The cabin was just as described, beautiful. The location is perfect and the view gorgeous. Just a minute from the main road which easily took us to the tours, restaurants, etc., both north and south of the property. Our questions were answered quickly, and local info was provided which gave us some guidance regarding popular points of interest. We had a great time!"
Cozy Chateau cabin with hot tub, pool table, and view of Seneca Lake, close to 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!

Pet-Friendly Ovid Home Near Seneca Lake & Wineries

9.0 out of 10, Wonderful, (31)
"We had a great time in this home. Short drive to the wineries, quiet neighborhood. Everything as described - including the steep stairs. We were even given snacks and coffee! Thank you!"
Pet-Friendly Ovid Home Near Seneca Lake & Wineries

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.

Panoramic Seneca Lake Views, On Wine Trail, Open Floorpan, Huge Firepit Area

9.0 out of 10, Wonderful, (36)
"This place is absolutely stunning. The views from the house are incredible. We even got to see horses next door. Very close to a lot of wineries and breweries. We will be returning!"
Panoramic Seneca Lake Views, On Wine Trail, Open Floorpan, Huge Firepit Area

Enchanted Hill: rural home with a hot tub and view, close to Keuka Lake

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay at Enchanted Hill. The house was clean, nicely decorated, and very well appointed. The kitchen, outdoor deck, and view were our favorite parts. The three bedrooms and three bathrooms worked very well for the six of us. There were two comfortable rooms to sit or watch TV, and the large kitchen was very convenient. The house is in a private setting with much property, and sitting on the deck or in the hot tub was a joy. Communication with Linger Hospitality was timely and very...
Enchanted Hill: rural home with a hot tub and view, close to Keuka Lake

Papa`s Paradise: rural home on Waneta Lake with private lakefront, pool table

9.6 out of 10, Exceptional, (50)
"The listing matched the house, cleanliness, and great communication with the management company. We enjoyed the sunset and sunrise from this location and watching the fishermen running up and down the lake or trolling in the area. The house was a good size for family to dine together and laugh and play games in the spacious living room."
Papa`s Paradise: rural home on Waneta Lake with private lakefront, pool table

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

10.0 out of 10, Exceptional, (71)
"perfect place to stay! There were 7 of us, it was easy to get to the wineries on Seneca Lake. The view of the lake, the dock with glider and the chairs around the firepit made the trip, we spent a lot of time outback enjoying the view. The rooms were cozy. The house was very comfortable to hang out in, we didn’t even use all the rooms to sit in, there is a great amount of space. The kitchen is perfect set up and the 2nd fridge space really helped. Overall, great trip with friends. "
Best Value on Seneca Lake! RARE Level Lakefront on the Wine Trail!

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

9.8 out of 10, Exceptional, (80)
"Absolutely beautiful house with stunning views!"
Castello: modern cabin with hot tub, pool table and Seneca lake view, along wine trail

The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

10.0 out of 10, Exceptional, (65)
"Stop in this area on our way back West after visiting New Hampshire. Clean and comfortable, but was a bit overpriced. Otherwise everything was good."
The price is AED 643
AED 1,103 total
includes taxes & fees
22 Dec - 23 Dec
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

Cayuga Cottage [Bella Vista Cottages]

9.8 out of 10, Exceptional, (11)
"We loved the location, the views and how spacious the house was. "
The price is AED 713
AED 1,488 total
includes taxes & fees
23 Dec - 24 Dec
Cayuga Cottage [Bella Vista Cottages]

Enjoy Cabin Vibes & Lake Views, Close to DT, lake and Finger Lakes Activities

10.0 out of 10, Exceptional, (21)
"This place is absolutely perfect for entertaining! Open kitchen/dining room with small lounge area upstairs. The kitchen has absolutely everything. We cooked a Thanksgiving dinner for 8 with no frustrations! The downstairs, using the open staircase, has 3 beds and comfortable living area. The upstairs also has a master bedroom with a fabulous bathroom and very large shower with multi shower heads! Also no worries about keeping warm in cold weather with 2 gas fireplaces and individual...
The price is AED 1,282
AED 2,516 total
includes taxes & fees
22 Dec - 23 Dec
Enjoy Cabin Vibes & Lake Views, Close to DT, lake and Finger Lakes Activities

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

Fully furnished yr round home near Seneca Lake, on Wine trail, Family Friendly

9.0 out of 10, Wonderful, (4)
"We just wanted a little place to stay away for a weekend. This house was everything and more than we wanted! The hosts were great to work with. "
The price is AED 735
AED 1,936 total
includes taxes & fees
21 Dec - 22 Dec
Fully furnished yr round home near Seneca Lake, on Wine trail, Family Friendly

Robust vacation home near nature and ski mountains in the Finger Lakes region!

9.8 out of 10, Exceptional, (6)
"Beautiful house tucked away in the woods! The house was very well appointed with everything we could ever need! The provided coffee, cream and sugar was a nice extra touch! We enjoyed the hot tub and walking in the woods. Obviously no fault of the owner but we did find ticks on us after our hike so be aware to check for ticks after you go in the woods or use tick spray etc. Will be recommending this listing and likely to return!"
Robust vacation home near nature and ski mountains in the Finger Lakes region!
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

Retreat of falling waters

9.0 out of 10, Wonderful, (196)
"Cozy. The hot tub was great after a day of walking the many trails in the area"
Retreat of falling waters

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

8.8 out of 10, Excellent, (193)
"The location was ideal for what we wanted to do. The views were incredible"
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..

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

9.8 out of 10, Exceptional, (45)
"Beautiful view. Hard to overstate how gorgeous it is. Host provides a lot of helpful mod-cons that we didn't expect. Only major issue is ticks! If you bring a pet, do not let it stray from stone driveways and make sure it's up to date on preventive meds. Our (always leashed) dog must have brushed some high grass on walking trails on property and had more ticks on her than I have ever seen at once. "
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.