Photo by Matthew Jay

Holiday Rentals in Middlesex

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Holiday Rentals in Middlesex

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

8.8 out of 10, Excellent, (198)
"Perfect little getaway with the hot tub and a cozy and quiet hill. Glad we had the four-wheel-drive car to get up the hill!!!"
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.

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

10.0 out of 10, Exceptional, (104)
"Amazing location with a view that we never got tired of! So much space to enjoy the property with friends and family. Hope to be back!"
Lakeside Home, New Pool, Carriage House, level & private, 6 BR, 120' frontage!

Naples Valley Getaway! Private home with hot tub- 20 min. From Bristol Mountain

10.0 out of 10, Exceptional, (307)
"This is a beautiful home that’s located in a great spot. Close to breweries, wineries and Bristol Mountain, but far enough out of town that it’s private and peaceful. It’s clean and modern with all the amenities you could need. We loved our weekend! "
Naples Valley Getaway! Private home with hot tub- 20 min. From Bristol Mountain

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

Luxurious Log Cabin in Woods on Keuka Lake w Prvt Dock & Lake Front

10.0 out of 10, Exceptional, (182)
"We thoroughly enjoyed our stay here. It was an almost perfect late fall weekend and just loved being able to watch the sunrise from the comfort of our living room. Everything was as stated in the description. Having a heavy duty crew cab pickup presented an interesting endeavor getting turned around 😆, the driveway was very steep and not a ton of room. I managed. Skee Ball was a huge hit. Didn’t explore the dock since it was the last weekend of October. Would definitely consider staying there...
Luxurious Log Cabin in Woods on Keuka Lake w Prvt Dock & Lake Front

MAXWELL'S MOUNTAIN UPPER CABIN. AMAZING VIEWS!!WINECOUNTRY!!! HOT TUB ON DECK!!

9.0 out of 10, Wonderful, (54)
"We enjoyed our stay. We felt comfy and cozy here and look forward to many more stays in the future. Close to Canandaigua, Honeoye, Hornell. And our family. "
MAXWELL'S MOUNTAIN UPPER CABIN. AMAZING VIEWS!!WINECOUNTRY!!! HOT TUB ON DECK!!

Keuka East: Spacious & Comfy

9.6 out of 10, Exceptional, (132)
"Great location to enjoy wine at spots around Keuka Lake. "
Keuka East: Spacious & Comfy

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

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!

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!

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

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

Cozy new England style cottage Right on Wine and Beer Trail

9.8 out of 10, Exceptional, (253)
"The location of the Vrbo was perfect. We were going to an event called Deck the Halls at Seneca Lake in the Finger Lakes region. Vrbo was clean, quaint and quiet. A beautiful view of Seneca Lake. We all had a great time!"
Cozy new England style cottage Right on Wine and Beer Trail

Charming 2-story dog-friendly farmhouse with game room, firepit, deck, grill

10.0 out of 10, Exceptional, (13)
"Beautiful area, very large yard. House was very clean and had almost everything we needed. The water pressure was not good if more than one person was showering. That was the only negative thing we noticed. "
Charming 2-story dog-friendly farmhouse with game room, firepit, deck, grill

Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

9.8 out of 10, Exceptional, (129)
"The cabin was absolutely perfect! The hosts are very thoughtful, providing coffee, cups, towels and bedding along with other amenities to make you feel at home! Loved the seclusion but also close enough to activities in the area. I would highly recommended this place! I will definitely stay here again when in this area!enough"
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016

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

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

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
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 types of properties in Middlesex you may be interested in

The Lake House on Canandaigua

4.5 star property
9.4 out of 10, Exceptional, (277)
"Beautiful decor, good choices for dining, friendly service."
The price is €279
includes taxes & fees
16 Feb - 17 Feb
The Lake House on Canandaigua

41 Lakefront Hotel, Trademark Collection By Wyndham

3.0 star property
8.2 out of 10, Very good, (1003)
"Very friendly environment. "
The price is €106
includes taxes & fees
27 Jan - 28 Jan
41 Lakefront Hotel, Trademark Collection By Wyndham

Hampton Inn Penn Yan

2.5 star property
9.4 out of 10, Exceptional, (973)
"This hotel was absolutely perfect. It was extremely clean and spacious and you can’t beat the fact that it’s right on the lake and our room had a beautiful view of Keuka. The onsite restaurant had great food and the free breakfast buffet was nicer than expected. The hotel is very close to many wineries and it is also close to the town of Penn Yann where there are stores and restaurants. Next time I’m in the area I will definitely stay here again! "
The price is €79
includes taxes & fees
2 Feb - 3 Feb
Hampton Inn Penn Yan
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.

Frequently asked questions

Are there holiday rentals in Middlesex?

Yes, there are holiday rentals close to the most popular sights in Middlesex, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middlesex has to offer?

Lakefront gem with game room and dock - the house that almost floated away: This holiday home rental outside of Middlesex is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Middlesex?

Choose from 11 Expedia holiday rentals in Middlesex for a memorable holiday.

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 wider area, you’ll find West River Marsh and Bristol Mountain Ski Resort.

What are holiday rentals like in Middlesex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlesex. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.