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 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Middlesex vacation rentals

1. Beautiful Newly Renovated 1900s Farm House On 9 Acres

Beautiful Newly Renovated 1900s Farm House On 9 Acres
Rushville
10.0 out of 10, Exceptional, (1 review)
"Beautiful, private, place. We loved the outdoor fire. The bed was very comfortable. We had everything we needed."
United States
ERIC W.
$218 nightly
The price is $244
Sep 28 - Sep 29
Total with taxes and fees
Beautiful Newly Renovated 1900s Farm House On 9 Acres
A living room with a brown leather sofa, a wooden coffee table, a TV mounted on the wall, and a window with blinds.

2. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
"Owner never sent check/in information and never responded to calls or messages. So we never even saw the inside. Don’t book with this place!"
United States
Chrissy D.
$88 nightly
The price is $94
Sep 17 - Sep 18
Total with taxes and fees
Beautiful Tiny home Near The Lake

3. Lovely 1 Bed Ranch Close to all Attractions

Lovely 1 Bed Ranch Close to all Attractions
Canandaigua NY
4.0 out of 10, (1 review)
"There is NO house number on the building. The host did NOT provide us with info prior to arrival, we had to message him to get access. It appeared that check in was at 4:00, but turned out it was 3:00. The actual property appearance does NOT look like the pictures online. Outside is overgrown, dirty and cobweb’s everywhere. Inside smells musty and gross. Flies everywhere, spiders in the bathroom and shower. It was not clean under the bed. There’s no bathroom soaps or wash clothes and the towels...
United States
Anonymous traveler
$174 nightly
The price is $187
Sep 23 - Sep 24
Total with taxes and fees
Lovely 1 Bed Ranch Close to all Attractions
A group of Adirondack chairs arranged around a fire pit in a forested area with a small cabin in the background.

4. 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.
$239 nightly
The price is $268
Sep 12 - Sep 13
Total with taxes and fees
Savannah Safari Tent & Breakfast-FLX Glamping
A yurt with a central skylight, a bed with a 'OFFLINE' sign, a woven chair, and a patterned rug.

5. 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.
$212 nightly
The price is $237
Sep 13 - Sep 14
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.

6. 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.
$150 nightly
The price is $161
Oct 2 - Oct 3
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.

7. Finger Lakes Cottage

Finger Lakes Cottage
Prattsburgh
9.8 out of 10, Exceptional, (102 reviews)
"Cute place!"
United States
Jessica W.
$147 nightly
The price is $164
Sep 21 - Sep 22
Total with taxes and fees
Finger Lakes Cottage
A waterfall cascading over rocks into a pool, surrounded by greenery.

8. 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, (162 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
Sep 13 - Sep 14
Total with taxes and fees
Vacation Rental Cabin, Keuka Lake Outlet-Trail, Wine Trail. Brand New in 2016
A spacious living room with a large wooden dining table, a blue sofa, and a fireplace.

9. 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, (25 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
$478 nightly
The price is $514
Sep 20 - Sep 21
Total with taxes and fees
Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.
A modern kitchen with a central island, wooden chairs, and green cabinetry.

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

Charming country ranch in the hills of the Finger Lakes
Naples
10.0 out of 10, Exceptional, (11 reviews)
"great location ... well kept surroundings.."
United States
James L.
$429 nightly
The price is $433
Sep 14 - Sep 15
Total with taxes and fees
Charming country ranch in the hills of the Finger Lakes
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
Sep 14 - Sep 15
Total with taxes and fees
The Gathering Place: Rushville Home w/ Hot Tub
A bedroom with a bed, a nightstand, a window with curtains, a door, and a ceiling fan.

12. Private Backyard & Deck · Family-Friendly

Private Backyard & Deck · Family-Friendly
Penn Yan
10.0 out of 10, Exceptional, (5 reviews)
$365 nightly
The price is $409
Sep 14 - Sep 15
Total with taxes and fees
Private Backyard & Deck · Family-Friendly
A hot tub on a wooden deck with a clear sky and trees in the background.

13. Amazing Stargazing Retreat

Amazing Stargazing Retreat
Naples
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful home and property. Very clean, very quiet. The amenities were lovely and allowed for a restful getaway. Easy communication with host. Definitely recommend!"
United States
Becky H.
$462 nightly
The price is $498
Sep 13 - Sep 14
Total with taxes and fees
Amazing Stargazing Retreat
A bedroom with a bed, bedside table, lamp, and decorative vases.

14. Cozy Main St Studio - Penn Yan

Cozy Main St Studio - Penn Yan
Penn Yan
10.0 out of 10, Exceptional, (1 review)
"Absolutely beautiful studio, very clean and comfortable! Perfect location!"
United States
Erin D.
$265 nightly
The price is $269
Sep 13 - Sep 14
Total with taxes and fees
Cozy Main St Studio - Penn Yan
A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

15. Sub Level Effiency

Sub Level Effiency
Geneva
9.0 out of 10, Wonderful, (17 reviews)
"A great place to stay "
United States
Patrick
$88 nightly
The price is $97
Oct 1 - Oct 2
Total with taxes and fees
Sub Level Effiency
A spacious living room with a large window, a ceiling fan, and a flat-screen TV.

16. 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)
$489 nightly
The price is $525
Oct 6 - Oct 7
Total with taxes and fees
Lakefront Vibes & Wine Country 3BR Near Downtown, CMAC Canandaigua Lake Overlook
A house with a patio area featuring a fire pit, outdoor furniture, and a covered deck with an umbrella.

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

‘The Gathering Place’: Rushville Home w/ Hot Tub
Rushville
9.6 out of 10, Exceptional, (14 reviews)
"Great stay with good location. "
United States
Emma R.
$605 nightly
The price is $666
Sep 14 - Sep 15
Total with taxes and fees
‘The Gathering Place’: Rushville Home w/ Hot Tub
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.

18. One bedroom apartment in the finger lakes

One bedroom apartment in the finger lakes
Naples
10.0 out of 10, Exceptional, (1 review)
"Host was great with communications."
United States
Barbara G.
$319 nightly
The price is $343
Sep 14 - Sep 15
Total with taxes and fees
One bedroom apartment in the finger lakes
A spacious living room with a grey sectional sofa, a wooden coffee table, and a kitchen in the background.

19. 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)
$489 nightly
The price is $539
Sep 13 - Sep 14
Total with taxes and fees
Walkable Naples Wine Country 5BR Hot Tub Sleeps 16 Bristol Mountain
A house with a deck, outdoor seating, and a dock over water.

20. The Vita and Vine: Lakefront, Outdoor Theater

The Vita and Vine: Lakefront, Outdoor Theater
Rushville
$866 nightly
The price is $931
Oct 6 - Oct 7
Total with taxes and fees
The Vita and Vine: Lakefront, Outdoor Theater
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

Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton

10/10 Excellent
"I am handicapped and was very happy with my accessible room! Plus, the building itself was easy for us to get around in with me in a wheelchair or with a cane. Our room was very clean and beautifully designed. The accessible shower worked out great with the pull down seat and shower hose. We really enjoyed the walking paths by the beautiful lake, with the flowers and wildlife as well. We never had a problem getting a convenient handicap parking place. There are several available, which I've never seen anywhere else. We will definitely return to this hotel on our next excursion to Canandaigua Lake."
Karen 2-night trip
Posted 7 hours ago
Hotel Canandaigua, Tapestry Collection by Hilton

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 $224 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?

Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch: This vacation home rental outside of Middlesex is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.