A waterfall cascading through a narrow rock formation surrounded by greenery.

Middlesex Vacation Rentals

Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Middlesex vacation rentals

Property grounds

1. 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
$216 nightly
The price is $242
Aug 8 - Aug 9
Total with taxes and fees
Gypsy Belle Glamping Tent & Breakfast for 2 in Finger Lakes Wine Country!
Interior

2. 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.
$222 nightly
The price is $249
Aug 8 - Aug 9
Total with taxes and fees
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
Outdoor dining

3. That Cottage by the Lake!!

That Cottage by the Lake!!
Canandaigua
9.8 out of 10, Exceptional, (19 reviews)
"Beautiful property walkable to the lake, hosting awesome and communicates well and responds fast to messages, overall lovely place to stay!"
United States
Ava m.
$412 nightly
The price is $443
Aug 10 - Aug 11
Total with taxes and fees
That Cottage by the Lake!!
Smart TV

4. Ideal location for adventure all year round

Ideal location for adventure all year round
Naples
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and accommodating. Would stay again!!"
United States
Susan W.
$150 nightly
The price is $161
Aug 23 - Aug 24
Total with taxes and fees
Ideal location for adventure all year round
Exterior

5. 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
$252 nightly
The price is $282
Aug 9 - Aug 10
Total with taxes and fees
Sunny Trails Getaway Cabin
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, (1 review)
"This house was excellent. Very clean and had a well-stocked kitchen with everything you need. Also had plenty of towels for the family. The beds were very comfortable and it’s very quiet. Very easy to get to Penn Yan by car in a few minutes. We will definitely rent this property again."
United States
Amie M.
$401 nightly
The price is $449
Aug 10 - Aug 11
Total with taxes and fees
Private Backyard & Deck · Family-Friendly
Interior

7. Modern Studio - Main St Penn Yan

Modern Studio - Main St Penn Yan
Penn Yan
9.6 out of 10, Exceptional, (14 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.
$266 nightly
The price is $268
Aug 9 - Aug 10
Total with taxes and fees
Modern Studio - Main St Penn Yan
Coffee/tea maker, fridge, microwave, oven

8. 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, (9 reviews)
"great location ... well kept surroundings.."
United States
James L.
$429 nightly
The price is $433
Aug 8 - Aug 9
Total with taxes and fees
Charming country ranch in the hills of the Finger Lakes
Paper towels

9. One bedroom apartment in the finger lakes

One bedroom apartment in the finger lakes
Naples
$300 nightly
The price is $323
Sep 7 - Sep 8
Total with taxes and fees
One bedroom apartment in the finger lakes
Pool

10. 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, (157 reviews)
"The cabin and property was perfect for us, the only negative was a lack of water pressure using the shower."
United States
Jeffrey
$151 nightly
The price is $169
Aug 26 - Aug 27
Total with taxes and fees
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
1 bedroom, iron/ironing board, WiFi, bed sheets

11. Cozy Main St Studio - Penn Yan

Cozy Main St Studio - Penn Yan
Penn Yan
$265 nightly
The price is $269
Aug 9 - Aug 10
Total with taxes and fees
Cozy Main St Studio - Penn Yan
Interior

12. Finger Lakes Escape • FLX Chalet + Private Pond

Finger Lakes Escape • FLX Chalet + Private Pond
Branchport
10.0 out of 10, Exceptional, (10 reviews)
"Great place for a winter getaway!"
United States
Catherine K.
$520 nightly
The price is $576
Aug 13 - Aug 14
Total with taxes and fees
Finger Lakes Escape • FLX Chalet + Private Pond
Dining

13. Sub Level Effiency

Sub Level Effiency
Geneva
8.6 out of 10, Excellent, (13 reviews)
"A great place to stay "
United States
Patrick
$101 nightly
The price is $112
Aug 16 - Aug 17
Total with taxes and fees
Sub Level Effiency
Interior

14. Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.

Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.
Canandaigua
10.0 out of 10, Exceptional, (24 reviews)
"Everything was wonderful. Only comment I have is the “lake view” is just a small view between 2 houses across the street."
United States
John
Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.
Property grounds

15. 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.
$251 nightly
The price is $281
Aug 9 - Aug 10
Total with taxes and fees
Savannah Safari Tent & Breakfast-FLX Glamping
Terrace/patio

16. Casita: Near Wineries & Keuka Lake: 100"Projector

Casita: Near Wineries & Keuka Lake: 100"Projector
Bath
10.0 out of 10, Exceptional, (16 reviews)
"Excellent place to stay if you are looking for a secluded getaway with someone you love. Perfect for two people with enough amenities to make your stay relaxing. Communication with the host was fast and helpful. Would definitely recommend and stay here again. "
United States
Donald M.
$324 nightly
The price is $362
Aug 9 - Aug 10
Total with taxes and fees
Casita: Near Wineries & Keuka Lake: 100"Projector
Exterior

17. PIne View Meadow

PIne View Meadow
Gorham
9.6 out of 10, Exceptional, (25 reviews)
"We had a wonderful stay! The house was spotless and had plenty of space for everyone to relax comfortably. We were lucky enough to get snow while we were there, which made everything feel extra magical. The host even provided sleds so our kids could slide down the hill & it truly felt like a winter wonderland.The hosts were extremely responsive and went above and beyond to accommodate us, especially with some weather related travel issues while we were flying in. We couldn’t say enough good...
United States
Brandy N.
$1,760 nightly
The price is $1,845
Sep 1 - Sep 2
Total with taxes and fees
PIne View Meadow
TV

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

Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
Canandaigua
9.4 out of 10, Exceptional, (3 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.
$614 nightly
The price is $660
Sep 2 - Sep 3
Total with taxes and fees
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
Interior

19. Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail

Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail
Naples
$1,031 nightly
The price is $1,108
Sep 1 - Sep 2
Total with taxes and fees
Hilltop Escape: Epic Game Room, Lake Views, Fire Pit & Wine Trail
Coffee/tea maker, fridge, oven, stovetop

20. 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)
"It was cozy and welcoming, owner was prompt answering any questions"
United States
Andrew M.
$222 nightly
The price is $249
Aug 11 - Aug 12
Total with taxes and fees
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
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

Find out more about Middlesex

Everything you need to know about Middlesex vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesex vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlesex in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlesex rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 and wood-fired hot tub! Center of FLX wine country!: 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. You and your friends and family can relax into your vacation with amenities like a hot tub.

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.