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

Middlesex Vacation Rentals

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Check prices for these dates

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

Our top choices for Middlesex vacation rentals

A yurt with a central skylight, a bed with a 'OFFLINE' sign, a woven chair, and a patterned rug.

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.
$223 nightly
The price is $250
Aug 20 - Aug 21
Total with taxes and fees
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
A living room with a sectional sofa, a fireplace, and a large window.

2. 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.
$137 nightly
The price is $147
Aug 24 - Aug 25
Total with taxes and fees
Ideal location for adventure all year round
A cozy cabin interior with a sectional sofa, wooden ceiling, white cabinets, and a kitchenette.

3. Finger Lakes Cottage

Finger Lakes Cottage
Prattsburgh
9.8 out of 10, Exceptional, (102 reviews)
"Cute place!"
United States
Jessica W.
$155 nightly
The price is $174
Sep 10 - Sep 11
Total with taxes and fees
Finger Lakes Cottage
A waterfall cascading over rocks into a pool, surrounded by greenery.

4. 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, (159 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
A bedroom with a bed, a nightstand, a window with curtains, a door, and a ceiling fan.

5. 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.
$401 nightly
The price is $449
Aug 24 - Aug 25
Total with taxes and fees
Private Backyard & Deck · Family-Friendly
A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

6. Sub Level Effiency

Sub Level Effiency
Geneva
8.8 out of 10, Excellent, (15 reviews)
"A great place to stay "
United States
Patrick
$101 nightly
The price is $112
Aug 24 - Aug 25
Total with taxes and fees
Sub Level Effiency
A rustic log cabin with a porch, surrounded by trees.

7. 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
$256 nightly
The price is $286
Aug 20 - Aug 21
Total with taxes and fees
Sunny Trails Getaway Cabin
A modern kitchen with a central island, wooden chairs, and green cabinetry.

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, (10 reviews)
"great location ... well kept surroundings.."
United States
James L.
$429 nightly
The price is $433
Aug 24 - Aug 25
Total with taxes and fees
Charming country ranch in the hills of the Finger Lakes
A kitchen with a gas stove, oven, microwave, and a stainless steel refrigerator. There are potted plants on the counter and a sign on the wall.

9. One bedroom apartment in the finger lakes

One bedroom apartment in the finger lakes
Naples
$319 nightly
The price is $343
Sep 13 - Sep 14
Total with taxes and fees
One bedroom apartment in the finger lakes
A spacious living area with a kitchen, a sofa, and a dining table.

10. 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.
$281 nightly
The price is $285
Aug 23 - Aug 24
Total with taxes and fees
Modern Studio - Main St Penn Yan
A house with a patio area featuring a fire pit, outdoor furniture, and a covered deck with an umbrella.

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

The Gathering Place: Rushville Home w/ Hot Tub
3.0 star property
Rushville
$596 nightly
The price is $640
Aug 20 - Aug 21
Total with taxes and fees
The Gathering Place: Rushville Home w/ Hot Tub
A house with a patio area featuring a fire pit, outdoor furniture, and a covered deck with an umbrella.

12. ‘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.
$609 nightly
The price is $671
Aug 20 - Aug 21
Total with taxes and fees
‘The Gathering Place’: Rushville Home w/ Hot Tub
A modern kitchen with a large island, a sink, and a window overlooking a yard.

13. 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
$189 nightly
The price is $212
Sep 9 - Sep 10
Total with taxes and fees
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
A spacious living room with a grey sectional sofa, a wooden coffee table, and a kitchen in the background.

14. 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)
$570 nightly
The price is $628
Sep 1 - Sep 2
Total with taxes and fees
Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
A hallway with a wooden door, a console table with a mirror and flowers, and a patterned rug.

15. 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.
$547 nightly
The price is $613
Sep 15 - Sep 16
Total with taxes and fees
Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom
A dining room with a table set for four, wooden chairs, a vase with flowers, and a window with curtains.

16. 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.
$199 nightly
The price is $223
Aug 20 - Aug 21
Total with taxes and fees
Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake
A group of Adirondack chairs arranged around a fire pit in a forested area with a small cabin in the background.

17. 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.
$252 nightly
The price is $282
Aug 20 - Aug 21
Total with taxes and fees
Savannah Safari Tent & Breakfast-FLX Glamping
A spacious living room with a large window, a ceiling fan, and a flat-screen 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
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.
$535 nightly
The price is $575
Sep 10 - Sep 11
Total with taxes and fees
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
A bedroom with a bed, bedside table, lamp, and decorative vases.

19. Cozy Main St Studio - Penn Yan

Cozy Main St Studio - Penn Yan
Penn Yan
$269 nightly
The price is $273
Aug 24 - Aug 25
Total with taxes and fees
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

Hampton Inn Penn Yan

Hampton Inn Penn Yan

10/10 Excellent
"Beautiful lake view. Nicely manicured property. Good breakfast. Comfortable beds. Nice bathroom."
Patricia E 2-night trip
Posted 10 hours ago
Hampton Inn Penn Yan

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 $169 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 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.