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Middlesex Holiday Rentals

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Holiday Rentals in Middlesex

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
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, (189)
"We stayed here right after our wedding for a mini honeymoon. The location is private and quiet and just a very short drive to downtown Naples. The host were absolutely fabulous and wonderful with communication. We highly recommend! "
Nature Lovers Getaway Nestled In The Hills Of The Finger Lakes Region..
THE GRAPE ESCAPE - OFF GRID CABIN - Wine Trail & Lake View - Pet Friendly!
Property grounds

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!
Naples Valley Getaway! Private home with hot tub.
Outdoor dining

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.
creek's edge
Interior

creek's edge

9.8 out of 10, Exceptional, (17)
"Stayed for the night after going to a concert, amazing place felt very safe there and had no concerns!"
creek's edge
STARWOOD - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! 4 Seasons
Property grounds

STARWOOD - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! 4 Seasons

10.0 out of 10, Exceptional, (22)
"Thank you Dave and JoAnne for sharing beautiful property with us! It was peaceful, beautiful view, the cabin was clean and cozy, and so many little details and thought you put into things did not go unnoticed! You were responsive when we needed you, and so very friendly! Thank you again for a much needed getaway for my husband, our pup, and me ☺️"
STARWOOD - ROMANTIC - OFF GRID - WINE TRAIL CABIN - Pet Friendly! 4 Seasons
Cozy new England style cottage Right on Wine and Beer Trail
Terrace/patio

Cozy new England style cottage Right on Wine and Beer Trail

9.8 out of 10, Exceptional, (249)
" Our original plan was to stay for just one night, but as soon as we arrived at the house, we knew we had to extend our stay. It’s impossible to spend just one night at such a beautifully designed and well-maintained lake house! Our host was incredibly supportive, answered all our questions, and did their best to enhance our experience. We will definitely return to this wonderful place in the future!"
Cozy new England style cottage Right on Wine and Beer Trail
WELCOME! WE ARE PET FRIENDLY.
Outdoor dining

WELCOME! WE ARE PET FRIENDLY.

10.0 out of 10, Exceptional, (255)
"This was our 2nd time staying at this wonderful property It you are looking for privacy tranquility with all home conveniences, then this is the absolute best. We look forward to our return . I would love to see this area in the snowy winter months. It must be right out of a hallmark movie "
WELCOME! WE ARE PET FRIENDLY.
Pine Grove Cabin
Exterior detail

Pine Grove Cabin

9.0 out of 10, Wonderful, (2)
"Loved the place and the remoteness. The water pump wasn't working, but a solution was promptly provided. It wasn't the best situation, but it worked. Also, the second bed appeared to be a mattress pad behind the main bed. We ended up just sharing the bed for the duration of the stay. Would return, but would love those issues/inaccuracies to be fixed."
Pine Grove Cabin
Keuka East: Spacious & Comfy
Terrace/patio

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
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.

Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.

10.0 out of 10, Exceptional, (244)
"Nice property, there is a tricky spiral staircase. Also a strong sulfur smell in the shower when you first run it. Overall it was cozy and great."
Adirondack Style Lodge - Minutes from Keuka Lake, Wineries.
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
Pool

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
Exterior

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
Cozy Bungalow right on the Lake wine and brewery trail.
Sun-loungers

Cozy Bungalow right on the Lake wine and brewery trail.

9.6 out of 10, Exceptional, (23)
"We loved this property and will be back again! So close to everything!"
The price is AU$412
includes taxes & fees
30 Nov - 1 Dec
Cozy Bungalow right on the Lake wine and brewery trail.
Croft Cove | 3 Bed, 2 Bath
Terrace/patio

Croft Cove | 3 Bed, 2 Bath

9.6 out of 10, Exceptional, (32)
"We had a nice weekend . The leaves were beautiful. Saturday night we enjoyed your fire pit . Thank you!"
Croft Cove | 3 Bed, 2 Bath
Pet-Friendly Ovid Home Near Seneca Lake & Wineries
Fridge, microwave, stovetop, dishwasher

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
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake
Terrace/patio

Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake

9.8 out of 10, Exceptional, (63)
"It is a great location rain or shine. The central living room is undersold online as we have had groups as big as 7 indoors all day due to rain without being on top of each other. Everything you need for your stay is there, and if it isn't Mary is able to help. Really a great little spot to relax and enjoy yourself. "
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake
MAXWELL'S MOUNTAIN UPPER CABIN. AMAZING VIEWS!!WINECOUNTRY!!! HOT TUB ON DECK!!
Outdoor dining

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

9.2 out of 10, Wonderful, (53)
"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!!
Recently Renovated 3 BR (Jewel) in the Heart of Finger Lakes
TV, fireplace

Recently Renovated 3 BR (Jewel) in the Heart of Finger Lakes

9.6 out of 10, Exceptional, (51)
"This was our 2nd time staying at this property, as we enjoyed it so much the first trip! We love that the cabin is quiet and private, while still being just a short drive to vineyards, lakes, restaurants and more. We did have to reset the router a few times as service would cut out, but that’s no biggie (and expected with the amount of wind when we visited). Such a wonderful place to relax, with all the comforts of home. We can’t wait to return for a 3rd time!"
Recently Renovated 3 BR (Jewel) in the Heart of Finger Lakes
Secluded Oasis: Luxurious Retreat with Stunning Views
Fridge, microwave, oven, stovetop

Secluded Oasis: Luxurious Retreat with Stunning Views

10.0 out of 10, Exceptional, (23)
"This is our second trip to this property, and it continues to be a stress free and relaxing excursion. The home is set up with everything you could want, and stuff you didn’t know you needed (like a towel warmer!). And the hosts are the best… friendly, organized, and just good people."
Secluded Oasis: Luxurious Retreat with Stunning Views
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

41 Lakefront Hotel, Trademark Collection By Wyndham
Courtyard

41 Lakefront Hotel, Trademark Collection By Wyndham

3.0 star property
8.2 out of 10, Very good, (1015)
"Only one elevator working. Pool not open "
The price is AU$181
includes taxes & fees
25 Nov - 26 Nov
41 Lakefront Hotel, Trademark Collection By Wyndham
The Lake House on Canandaigua
Seasonal outdoor pool

The Lake House on Canandaigua

4.5 star property
9.4 out of 10, Exceptional, (254)
"The property is very picturesque. The views of the lake and of the woods from the rooms was great. We had a woods view with a very large balcony which was nice. The rooms were well appointed and the bed was comfortable. Walking actions the property we saw the seating areas which at night were lit by the fire pits strong the property. Everything smelled nice and the staff were all helpful and friendly. We will definitely go back again. "
The price is AU$457
includes taxes & fees
9 Dec - 10 Dec
The Lake House on Canandaigua
Holiday Inn Express Canandaigua - Finger Lakes, an IHG Hotel
Exterior

Holiday Inn Express Canandaigua - Finger Lakes, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (1022)
"Good for one night stay. There were only supplies in the room for one. They were doing some work and hoses and extension cords were a bad trip hazard in the main hallways"
The price is AU$154
includes taxes & fees
28 Nov - 29 Nov
Holiday Inn Express Canandaigua - Finger Lakes, an IHG Hotel
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.
Beautiful view of the beach with palm trees

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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?

Retreat of falling waters: 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. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Middlesex?

Choose from 10 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.