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Compare 438 Vacation Homes in Middlesex with updated reviews, rates, and availability.

Naples Valley Getaway! Private home with hot tub.
Exterior
Naples Valley Getaway! Private home with hot tub.
10.0 out of 10, Exceptional, (300)
"My husband and I stayed at this beautiful property for our anniversary weekend. It was just what we needed. Clean, cozy and quiet. Would definitely return! "
Naples Valley Getaway! Private home with hot tub.
Vineyard Farmhouse w/ Hot Tub + Lake Views
Lakeview from Front Deck
Vineyard Farmhouse w/ Hot Tub + Lake Views
9.0 out of 10, Wonderful, (6)
"Clean and comfortable accommodations near Hammondsport. Water did have a slight sulfur smell but otherwise was a great place to stay and relax! Loved coming home and relaxing in the hot tub after a day at the wineries."
Vineyard Farmhouse w/ Hot Tub + Lake Views
On Cloud Wine | 5 Bed, 3 Bath
On Cloud Wine on Keuka Lake
On Cloud Wine | 5 Bed, 3 Bath
10.0 out of 10, Exceptional, (2)
"Wow! This is an amazing property in a stunning location on Keuka lake. We had a fabulous time!"
On Cloud Wine | 5 Bed, 3 Bath
New! Panorama Lakeview Place: Canandaigua Lake escape w pool, game room & more!
Exterior
New! Panorama Lakeview Place: Canandaigua Lake escape w pool, game room & more!
2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was lovely and comfortable for our group of 6 friends who came to celebrate a milestone birthday.There's plenty of spaces to be together and have private time.Views are spectacular.The check in was easy and the host was quick to responding to any questions we had.Would definitely come back."
New! Panorama Lakeview Place: Canandaigua Lake escape w pool, game room & more!
"Thyme Away" - A quiet home in the country
hot tub and sitting area!
"Thyme Away" - A quiet home in the country
9.6 out of 10, Exceptional, (50)
"David and Holly's place was perfect for our weekend getaway to visit our son. They had thought of every convenience... a wonderful assortment of coffees, farm fresh eggs, and the most delicious homemade bread. They even had disposable slippers for going to and from the hot tub!! The house was centrally located for all our sightseeing and was very peaceful. My favorite part had to be the beautiful sunrises every morning. We will definitely book again."
"Thyme Away" - A quiet home in the country
Serenity Place | 5 Bed, 3 Bath
Beautiful views of Seneca Lake through the large windows
Serenity Place | 5 Bed, 3 Bath
10.0 out of 10, Exceptional, (85)
"Great views of Seneca Lake! A very spacious house with many amenities for a four couple gateway. We had a lovely stay overall, but we did notice that the outdoor grounds and inside lights could use a bit more attention, as there were many bugs and cobwebs in certain areas. A little extra care in that regard would make the property even more enjoyable. Thank you for hosting us!"
Serenity Place | 5 Bed, 3 Bath
Relaxing Lakeview Retreat! Pool, Hot Tub, Firepit, Gameroom Perfect for Groups,
Our home is located on 1.5 acres and offers beautiful views of Lake Keuka
Relaxing Lakeview Retreat! Pool, Hot Tub, Firepit, Gameroom Perfect for Groups,
9.8 out of 10, Exceptional, (12)
"Extremely well organized. Host thought of everything! Lots of fun spaces to hang out. We all had a wonderful time."
Relaxing Lakeview Retreat! Pool, Hot Tub, Firepit, Gameroom Perfect for Groups,
Rustic Ridge Log Cabin
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Rustic Ridge Log Cabin
9.4 out of 10, Exceptional, (49)
"Its the cabin I've been searching for for years, Its very clean and the outside environment is very spacious. The outside bathroom was very clean. It does have solar powered lights but they dont last forever so bring lanterns, There is no running water so plan for that, There was evidence of mice so if that creeps you out then dont rent. Its very secluded so Animals are expected. Ive already rebooked. There was no coffee pot so i brought my own propane coffee pot because that porch was too...
The price is AED 255
AED 502 total
includes taxes & fees
17 Nov - 18 Nov
Rustic Ridge Log Cabin
Charming 2-story dog-friendly farmhouse with game room, firepit, deck, grill
Charming 2-story dog-friendly farmhouse with game room, firepit, deck, grill
10.0 out of 10, Exceptional, (12)
"We loved the area and the property "
Charming 2-story dog-friendly farmhouse with game room, firepit, deck, grill
Large Lakeview Lodge on Canandaigua Lake
Exterior
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
Chalet | 3 Bed, 2 Bath
Outside patio area
Chalet | 3 Bed, 2 Bath
10.0 out of 10, Exceptional, (32)
"The property was exceptional. It was probably one of the nicest places we’ve stayed and definitely the nicest in the Finger Lakes. We would stay here again in a heartbeat. "
Chalet | 3 Bed, 2 Bath
Seneca Lake View Retreat sits secluded on a 2 acre lot.
You’ll love the wrap around deck for hours of family gatheings.
Seneca Lake View Retreat sits secluded on a 2 acre lot.
10.0 out of 10, Exceptional, (6)
"The place was exactly as it looked in the App. Greg was more than gracious when I reached out for guidance on something I should have figured it. Beautiful, scenic, and close to everything. We plan on coming back. "
The price is AED 731
AED 1,671 total
includes taxes & fees
17 Nov - 18 Nov
Seneca Lake View Retreat sits secluded on a 2 acre lot.
FLAT YARD right on the LAKE!!
Living area
FLAT YARD right on the LAKE!!
9.0 out of 10, Wonderful, (4)
"Beautiful water front property- newly remodeled and set up nicely for friends and family. Most windows are without curtains causing limited privacy especially in the bathroom in the back house. There is only one television in the front home and you need your personal Roku sign on to use- that information would have useful prior to the visit. Normally television access is not something we would be concerned with however this weekend had football and baseball games we would of enjoyed watching...
FLAT YARD right on the LAKE!!
The Lodge at Pine Summit
Beautiful 32 acres including multiple walking trails
The Lodge at Pine Summit
9.6 out of 10, Exceptional, (21)
"We were 5 couples in town for a wedding. House was a great fit, well stocked, with plenty of room for everyone to spread out or be together. The beautiful grounds were an added bonus as we enjoyed some botchy ball, and walks around the property. Would definitely recommend this house and would stay again! Hosts were great with terrific communications!"
The price is AED 2,270
AED 5,109 total
includes taxes & fees
18 Nov - 19 Nov
The Lodge at Pine Summit
Spacious ‘GEM’ of the city
Kitchen
Spacious ‘GEM’ of the city
9.8 out of 10, Exceptional, (22)
"It was a lovely home and perfect for our reunion. The owner was very nice and was so accommodating. Had a great time recalling old times and catching up. "
The price is AED 768
AED 1,234 total
includes taxes & fees
17 Nov - 18 Nov
Spacious ‘GEM’ of the city
Penn Yan House Rental - Close to Wineries!
Penn Yan Vacation Rental | 2BR | 1.5BA | Stairs Required | 800 Sq Ft
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!
Fully furnished yr round home near Seneca Lake, on Wine trail, Family Friendly
Living area
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 1,947 total
includes taxes & fees
18 Nov - 19 Nov
Fully furnished yr round home near Seneca Lake, on Wine trail, Family Friendly
Year-round, beautiful lake front home on Canandaigua Lake. 20-min to Ski Resorts
South end of Canandaigua Lake
Year-round, beautiful lake front home on Canandaigua Lake. 20-min to Ski Resorts
10.0 out of 10, Exceptional, (7)
"Very cute and clean. Location was fabulous and quiet. Host was great to communicate. Overall we had a great time"
The price is AED 735
AED 1,605 total
includes taxes & fees
17 Nov - 18 Nov
Year-round, beautiful lake front home on Canandaigua Lake. 20-min to Ski Resorts
Retreat of falling waters
Exterior
Retreat of falling waters
9.0 out of 10, Wonderful, (195)
"Cute cottage brought me back to my childhood cottage on the lake, but instead this was tucked away in the woods. The road is close, but you cannot see it or hear it as the house is set back. It served our needs & close to area's we wanted to visit. There was a note saying enjoy our complimentary bottle of wine which we could not find, but This was ok because we had plenty. The house is set on a small hill with a rail on the right side & shale rock path which was a little slippery when it...
Retreat of falling waters
Seneca Vista | 3 Bed, 2.5 Bath
Street view of Seneca Vista
Seneca Vista | 3 Bed, 2.5 Bath
9.6 out of 10, Exceptional, (49)
"The house was amazing and we loved staying there on our wine trip!"
Seneca Vista | 3 Bed, 2.5 Bath
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

Naples Valley Getaway! Private home with hot tub.
Exterior
Naples Valley Getaway! Private home with hot tub.
10.0 out of 10, Exceptional, (300)
"My husband and I stayed at this beautiful property for our anniversary weekend. It was just what we needed. Clean, cozy and quiet. Would definitely return! "
Naples Valley Getaway! Private home with hot tub.
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, (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!
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, (188)
"Nice fall quiet anniversary getaway to the naples area. Went to Bristol Mountain festival, did some hiking, great diner at the Naples Hotel. ...all beautiful in the fall. My husband loved the arcade 🕹 game, and we enjoyed the hot tub, and firepit. "
Nature Lovers Getaway Nestled In The Hills Of 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.