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Middlesex Vacation Rentals

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Vacation Rentals in Middlesex

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Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes

Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes

Cohocton
10.0 out of 10, Exceptional, (16)
"Great property with a wonderful host!!!!"
United States
Scott M.
The price is ￥21,200
￥27,262 total
includes taxes & fees
Nov 22 - Nov 23
Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes
Exterior
Lakeside Home, New Pool, Carriage House, level & private, 6 BR, 120' frontage!

Lakeside Home, New Pool, Carriage House, level & private, 6 BR, 120' frontage!

Canandaigua
10.0 out of 10, Exceptional, (115)
"This property was great!"
United States
Maddy G.
Lakeside Home, New Pool, Carriage House, level & private, 6 BR, 120' frontage!
Property grounds
Wildflower-Seneca Lake-Water View-Hot Tub-Wine Trail - Pets, Steps to Lake-Acre of Privacy

Wildflower-Seneca Lake-Water View-Hot Tub-Wine Trail - Pets, Steps to Lake-Acre of Privacy

Dresden
8.6 out of 10, Excellent, (104)
"The property was clean, and very convenient to all that we wanted to do. We did not use the hot tub as we weren't interested in that. Overall a great week's stay. Pics of the lake views on the site need updating to reflect actual views. It was my only disappointment as it was a factor in selecting this rental. "
United States
p r.
Wildflower-Seneca Lake-Water View-Hot Tub-Wine Trail - Pets, Steps to Lake-Acre of Privacy
Exterior
Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!

Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!

Rushville
9.6 out of 10, Exceptional, (65)
"Beautiful property with wonderful amenities. Very comfortable and spacious. We loved every minute of it. "
United States
Mary Kay M.
Large Lakefront Lodge on Canandaigua Lake Sleeps 22 Guests!
Property grounds
Seneca Lake Home Finger Lakes Wineries Galore 4 BED 4 BATH

Seneca Lake Home Finger Lakes Wineries Galore 4 BED 4 BATH

Lodi
10.0 out of 10, Exceptional, (177)
"This was a great property. The host was very friendly and gave us some great information on restaurants. There were many water toys to enjoy and a great fire pit. "
United States
MaryEllen A.
Seneca Lake Home Finger Lakes Wineries Galore 4 BED 4 BATH
Interior
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.

Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.

Branchport
10.0 out of 10, Exceptional, (275)
"I had a great stay! The cabin was just what I was hoping for and communication with the host was top notch Thank you Gary and Dawn for your hospitality "
United States
Patti S.
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.
Property grounds
FROG HOUSE - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! Year round.

FROG HOUSE - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! Year round.

2.0 star property
Prattsburgh
9.2 out of 10, Wonderful, (14)
"Very nice off grid cabin we had a great time with my dog "
United States
James D.
FROG HOUSE - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! Year round.
Outdoor dining
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!

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

3.0 star property
Penn Yan
9.8 out of 10, Exceptional, (79)
"Great little place with everything you need. Host was very attentive with any questions we had. "
United States
Steve S.
The price is ￥24,734
￥46,698 total
includes taxes & fees
Nov 22 - Nov 23
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!
Exterior
Sunflower-Keuka/Seneca-Lake View-Hot Tub-Wine Trail-Pets, 13 Wooded Acres-7 min to Beach

Sunflower-Keuka/Seneca-Lake View-Hot Tub-Wine Trail-Pets, 13 Wooded Acres-7 min to Beach

Barrington
9.6 out of 10, Exceptional, (97)
"Very nice place. It felt very homey and was perfect for our winery tours!"
United States
Daisy C.
Sunflower-Keuka/Seneca-Lake View-Hot Tub-Wine Trail-Pets, 13 Wooded Acres-7 min to Beach
Property grounds
Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI

Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI

Penn Yan
9.8 out of 10, Exceptional, (252)
"Great waterfront area for swimming, lounging, picnic and evening fire. "
United States
Kevin D.
Beautiful Retreat w/Amazing Views-Kayak&Canoe! Lakefront! Free WIFI
Property grounds
Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch

Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch

Dundee
9.2 out of 10, Wonderful, (106)
"Very nice. Was a perfect accommodation for our family."
United States
Maureen A L.
Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch
Property grounds
Lakefront gem with game room and dock - the house that almost floated away

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

Penn Yan
9.2 out of 10, Wonderful, (60)
"The amount of rooms was perfect for our group of adults and kids. The basement play area was a hit, and so was the access tot he lake. House was very clean, and had lots of parking as well as rooms for everyone."
United States
Joshua B.
Lakefront gem with game room and dock - the house that almost floated away
Property grounds
Relaxing Lakeview Retreat! Pool, Hot Tub, Firepit, Gameroom Perfect for Groups,

Relaxing Lakeview Retreat! Pool, Hot Tub, Firepit, Gameroom Perfect for Groups,

Penn Yan
10.0 out of 10, Exceptional, (22)
"Perfect location"
United States
Nan M.
Relaxing Lakeview Retreat! Pool, Hot Tub, Firepit, Gameroom Perfect for Groups,
Exterior detail
Bear creek cabin, peaceful escape

Bear creek cabin, peaceful escape

Ovid
8.6 out of 10, Excellent, (4)
"The location of cabin was ideal for our itinerary. "
United States
Jeanna-Mar S.
Bear creek cabin, peaceful escape
Property grounds
THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!

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

Hammondsport
10.0 out of 10, Exceptional, (62)
"Cozy, secluded, private getaway with an incredible view of Keuka Lake"
Canada
Martin S.
THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!
Terrace/patio
Peaceful Hilltop Retreat Near Keuka Lake & Wine Trails

Peaceful Hilltop Retreat Near Keuka Lake & Wine Trails

Penn Yan
10.0 out of 10, Exceptional, (26)
"Beautiful home that was immaculate. Thank you for a wonderful stay."
United States
Michelle T.
Peaceful Hilltop Retreat Near Keuka Lake & Wine Trails
Terrace/patio
Romantic Cabin On-the-Water Breathtaking View Beach Fire Pit! 1 Wk Avail Jul'26

Romantic Cabin On-the-Water Breathtaking View Beach Fire Pit! 1 Wk Avail Jul'26

Hammondsport
9.2 out of 10, Wonderful, (190)
"We had a great time at No Such Place! Keith was a very accommodating host; he answered my many questions in advance and was very gracious. He met us on site at our arrival and was very welcoming. We enjoyed the cozy cabin feel and its setting along the shores of Keuka lake! Though the weather did not cooperate with much time outside, the view was amazing. Our party of 6 had a lovely weekend! "
United States
Susan
Romantic Cabin On-the-Water Breathtaking View Beach Fire Pit! 1 Wk Avail Jul'26
Terrace/patio
Keuka East: Spacious & Comfy

Keuka East: Spacious & Comfy

Penn Yan
9.8 out of 10, Exceptional, (148)
"Comfortable, well stocked, clean house. We had a great experience for our family reunion."
United States
Janice K.
Keuka East: Spacious & Comfy
Smart TV, fireplace, foosball, books
Panorama Lakeview Place: A Retreat for Every Season-Near Bristol Mountain & Lake

Panorama Lakeview Place: A Retreat for Every Season-Near Bristol Mountain & Lake

2.0 star property
Naples
9.6 out of 10, Exceptional, (23)
"This was a great home to stay in, absolutely beautiful! Very updated, high quality. "
United States
Liz G.
Panorama Lakeview Place: A Retreat for Every Season-Near Bristol Mountain & Lake
Property grounds
Serenity Zen House on Seneca Lake - Pet Friendly

Serenity Zen House on Seneca Lake - Pet Friendly

Penn Yan
9.8 out of 10, Exceptional, (178)
"Nice location and fun times"
United States
RICHARD B.
Serenity Zen House on Seneca Lake - 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.
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Top Middlesex Hotel Reviews

Hampton Inn Penn Yan

Hampton Inn Penn Yan

10/10 Excellent
"Great setting! Well pleased!"
Carvel 1-night trip
Posted 3 days ago
Hampton Inn Penn Yan

Find out more about Middlesex

Search for holiday rentals in Middlesex on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesex using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middlesex!

Frequently asked questions

Are there vacation rentals in Middlesex?

Yes, we offer vacation rentals near popular attractions in Middlesex, or you can go with a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Middlesex?

Seneca Lake Home Finger Lakes Wineries Galore 4 BED 4 BATH: This vacation home rental outside of Middlesex is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a private yard and a selection of books.

How many vacation rentals will I find in Middlesex?

Choose from 12 Expedia vacation rentals in Middlesex for a memorable vacation.

What can I see and do in Middlesex?

Canandaigua Lake and Clarks Gully are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find West River Marsh and Bristol Mountain Ski Resort.

What are vacation rentals like in Middlesex?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Middlesex. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip.