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Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Middlesex vacation rentals

Interior

1. Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Rushville
9.2 out of 10, Wonderful, (5 reviews)
"We so much enjoyed our two night's stay at Rainey and Jeff's campground and can't wait to return. Upon arrival, Rainey showed us around the campground, led us to our adorably decorated yurt and invited us to join the campfire later that evening for gourmet smores. We opened a bottle of wine and sat on the egg swings for a while, enjoying the sound of the bullfrogs and the beautiful surroundings. Later we enjoyed sitting by the campfire talking with the other guests and Rainey and Jeff. After a...
United States
Stephanie M.
The price is AED 643
AED 909 total
includes taxes & fees
18 Aug - 19 Aug
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Property grounds

2. Gypsy Belle Glamping Tent & Breakfast for 2 in Finger Lakes Wine Country!

Gypsy Belle Glamping Tent & Breakfast for 2 in Finger Lakes Wine Country!
Rushville
10.0 out of 10, Exceptional, (5 reviews)
"Amazing setup and the owners were Amazing. Definitely will be back. "
United States
Andrea
The price is AED 624
AED 889 total
includes taxes & fees
18 Aug - 19 Aug
Gypsy Belle Glamping Tent & Breakfast for 2 in Finger Lakes Wine Country!
Smart TV

3. Ideal location for adventure all year round

Ideal location for adventure all year round
Naples
10.0 out of 10, Exceptional, (7 reviews)
"house was clean, quiet area, perfect for my one night stay for a wedding"
United States
Alexis M.
The price is AED 430
AED 541 total
includes taxes & fees
24 Aug - 25 Aug
Ideal location for adventure all year round
Smart TV, fireplace, books

4. Finger Lakes Cottage

Finger Lakes Cottage
Prattsburgh
9.8 out of 10, Exceptional, (102 reviews)
"Cute place!"
United States
Jessica W.
The price is AED 312
AED 638 total
includes taxes & fees
10 Sep - 11 Sep
Finger Lakes Cottage
Pool

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

Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
Penn Yan
9.8 out of 10, Exceptional, (158 reviews)
"The cabin and property was perfect for us, the only negative was a lack of water pressure using the shower."
United States
Jeffrey
The price is AED 479
AED 619 total
includes taxes & fees
26 Aug - 27 Aug
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
3 bedrooms, iron/ironing board, WiFi, bed sheets

6. Private Backyard & Deck · Family-Friendly

Private Backyard & Deck · Family-Friendly
Penn Yan
10.0 out of 10, Exceptional, (3 reviews)
"Great house. It was perfect for us. Clean, beds were comfy and location was quiet and beautiful."
United States
Emily W.
The price is AED 1,084
AED 1,785 total
includes taxes & fees
16 Sep - 17 Sep
Private Backyard & Deck · Family-Friendly
Dining

7. Sub Level Effiency

Sub Level Effiency
Geneva
8.8 out of 10, Excellent, (15 reviews)
"A great place to stay "
United States
Patrick
The price is AED 298
AED 410 total
includes taxes & fees
24 Aug - 25 Aug
Sub Level Effiency
Exterior

8. Sunny Trails Getaway Cabin

Sunny Trails Getaway Cabin
Cohocton
10.0 out of 10, Exceptional, (17 reviews)
"Very peaceful and relaxing place"
United States
Orlando
The price is AED 711
AED 1,051 total
includes taxes & fees
20 Aug - 21 Aug
Sunny Trails Getaway Cabin
Coffee/tea maker, fridge, microwave, oven

9. Charming country ranch in the hills of the Finger Lakes

Charming country ranch in the hills of the Finger Lakes
Naples
9.8 out of 10, Exceptional, (10 reviews)
"great location ... well kept surroundings.."
United States
James L.
The price is AED 826
AED 1,591 total
includes taxes & fees
18 Aug - 19 Aug
Charming country ranch in the hills of the Finger Lakes
Paper towels

10. One bedroom apartment in the finger lakes

One bedroom apartment in the finger lakes
Naples
The price is AED 595
AED 1,133 total
includes taxes & fees
13 Sep - 14 Sep
One bedroom apartment in the finger lakes
Interior

11. Modern Studio - Main St Penn Yan

Modern Studio - Main St Penn Yan
Penn Yan
9.6 out of 10, Exceptional, (15 reviews)
"My girlfriend and i went on our first trip together here. It was very cozy! Was walking distance to all the things we wanted to do. We were planning another trip before the weekend was even over. "
United States
Kevin G.
The price is AED 536
AED 1,047 total
includes taxes & fees
23 Aug - 24 Aug
Modern Studio - Main St Penn Yan
House (4 Bedrooms) | Interior

12. The Gathering Place: Rushville Home w/ Hot Tub

The Gathering Place: Rushville Home w/ Hot Tub
3.0 star property
Rushville
The price is AED 1,289
AED 2,352 total
includes taxes & fees
18 Aug - 19 Aug
The Gathering Place: Rushville Home w/ Hot Tub
Terrace/patio

13. ‘The Gathering Place’: Rushville Home w/ Hot Tub

‘The Gathering Place’: Rushville Home w/ Hot Tub
Rushville
9.4 out of 10, Exceptional, (12 reviews)
"Great stay with good location. "
United States
Emma R.
The price is AED 1,061
AED 2,463 total
includes taxes & fees
18 Aug - 19 Aug
‘The Gathering Place’: Rushville Home w/ Hot Tub
Coffee/tea maker, fridge, oven, stovetop

14. Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!

Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
Penn Yan
8.8 out of 10, Excellent, (8 reviews)
"Very peaceful 3 days. Amenities were as expected."
United States
alan
The price is AED 470
AED 835 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
Smart TV, books

15. Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain

Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
Naples
10.0 out of 10, Exceptional, (1 review)
The price is AED 818
AED 2,138 total
includes taxes & fees
19 Aug - 20 Aug
Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
Interior

16. Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom

Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom
Penn Yan
10.0 out of 10, Exceptional, (7 reviews)
"We love the area. The house was very clean and had fun activities for us to do while there!"
United States
Renee S.
The price is AED 757
AED 2,423 total
includes taxes & fees
16 Sep - 17 Sep
Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom
Dining

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

Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
PennYan
9.6 out of 10, Exceptional, (163 reviews)
" Nice place. Convenient to nearby attractions. "
United States
Douglas K.
The price is AED 643
AED 819 total
includes taxes & fees
19 Aug - 20 Aug
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
Property grounds

18. Savannah Safari Tent & Breakfast-FLX Glamping

Savannah Safari Tent & Breakfast-FLX Glamping
Rushville
10.0 out of 10, Exceptional, (10 reviews)
"Great location, amazing hosts, wonderful morning breakfasts and coffee served! Good relaxation experience, swimming pond was awesome, going back next summer!"
United States
Faithann B.
The price is AED 735
AED 1,037 total
includes taxes & fees
18 Aug - 19 Aug
Savannah Safari Tent & Breakfast-FLX Glamping
TV

19. Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook

Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
Canandaigua
8.0 out of 10, Very Good, (5 reviews)
"Our stay worked out really well for us. Nice view of the lake. The deck actually has a covered gazebo! "
United States
Corey P.
The price is AED 995
AED 2,215 total
includes taxes & fees
16 Sep - 17 Sep
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
1 bedroom, iron/ironing board, WiFi, bed sheets

20. Cozy Main St Studio - Penn Yan

Cozy Main St Studio - Penn Yan
Penn Yan
The price is AED 496
AED 1,003 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Main St Studio - 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.
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Top Middlesex Hotel Reviews

Savannah House Wine Country Inn & Cottages

Savannah House Wine Country Inn & Cottages

10/10 Excellent
"We stayed there for two nights. Everything was perfect. Room was clean and check in and out was perfect. We will definitely recommend this place to friends. Given a chance we will come back again someday. "
Baisakhi 3-night trip
Posted 3 hours ago
Savannah House Wine Country Inn & Cottages

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?

Cozy Cabin With 165 Ft Beach in the heart of FLX wine country! ALL are welcome!: This vacation home rental outside of Middlesex is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Middlesex?

Choose from 11 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.