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Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Middlesex vacation rentals

1 bedroom, WiFi, bed sheets
Pet Friendly Keuka Wagon

Mobile Home in Penn Yan

Pet Friendly Keuka Wagon
9.6 out of 10, Exceptional, (25 reviews)
"Such an amazing, unique, peaceful and beautiful weekend getaway destination. "
United States
Ashley J.
$175 nightly
The price is $182
Feb 4 - Feb 5
Total with taxes and fees
Pet Friendly Keuka Wagon
Smart TV
Cozy 1BDR APT in Vibrant Downtown Geneva

Apartment in Geneva

Cozy 1BDR APT in Vibrant Downtown Geneva
10.0 out of 10, Exceptional, (4 reviews)
"Didn’t get to vinyards, loved the accommodations though."
United Kingdom
laura r.
$208 nightly
The price is $230
Jan 14 - Jan 15
Total with taxes and fees
Cozy 1BDR APT in Vibrant Downtown Geneva
1 bedroom, WiFi, bed sheets
Casita: Near Wineries & Keuka Lake: 100"Projector

Cabin in Bath

Casita: Near Wineries & Keuka Lake: 100"Projector
9.8 out of 10, Exceptional, (7 reviews)
"This is a beautifully appointed tiny home, perfect for a quiet getaway! The decor is curated so tastefully, and the kitchen area equipped with stovetop and even olive oil and spices. The bed is comfortable and it was so nice to be able to bring our dog along. The hosts were lovely and provided quick and thoughtful communication. We enjoyed this quiet, lovely retreat, and it is close to wineries and not far from the Corning Museum of Glass, which we took the opportunity to visit. A great...
United States
Erika K.
$169 nightly
The price is $189
Jan 14 - Jan 15
Total with taxes and fees
Casita: Near Wineries & Keuka Lake: 100"Projector
Interior
Modern Studio APT in the Heart of Downtown Geneva

Apartment in Geneva

Modern Studio APT in the Heart of Downtown Geneva
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful apartment, very clean. Great location-walking distances to restaurants and shops"
United States
Brooke E.
$246 nightly
The price is $272
Jan 18 - Jan 19
Total with taxes and fees
Modern Studio APT in the Heart of Downtown Geneva
Outdoor dining
Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva

Apartment in Geneva

Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva
9.0 out of 10, Wonderful, (17 reviews)
"The space was very clean and provided nice proximity to the lake and things to do in the area. It was a great stay!"
United States
Kaitlyn D.
$149 nightly
The price is $165
Feb 1 - Feb 2
Total with taxes and fees
Cozy 1-bedroom apartment with AC and WiFi in enjoyable Geneva
Interior
Pet Friendly Keuka Yurt

Vacation Home in Penn Yan

Pet Friendly Keuka Yurt
9.6 out of 10, Exceptional, (28 reviews)
"Very pet friendly, great location to many local wineries. Will definitely stay here again. For a longer time."
United States
Ian B.
$184 nightly
The price is $191
Feb 9 - Feb 10
Total with taxes and fees
Pet Friendly Keuka Yurt
Miscellaneous
Charming Farmhouse Retreat

Vacation Home in Shortsville

Charming Farmhouse Retreat
10.0 out of 10, Exceptional, (16 reviews)
"Peaceful!!!"
United States
Kevin D.
$312 nightly
The price is $315
Jan 14 - Jan 15
Total with taxes and fees
Charming Farmhouse Retreat
Property grounds
Top of the Fingerlakes, relaxing retreat.

Vacation Home in Waterloo

Top of the Fingerlakes, relaxing retreat.
9.8 out of 10, Exceptional, (28 reviews)
"Very comfortable, clean, and felt like home. Will be booking here again in June."
United States
April
$177 nightly
The price is $197
Jan 14 - Jan 15
Total with taxes and fees
Top of the Fingerlakes, relaxing retreat.
Interior
Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom

Vacation Home in Penn Yan

Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom
10.0 out of 10, Exceptional, (5 reviews)
"Great property. Close to everything the town has to offer. Plenty of room for a family "
United States
Anonymous traveler
$498 nightly
The price is $558
Jan 14 - Jan 15
Total with taxes and fees
Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom
Exterior detail
Spacious ‘GEM’ of the city

Vacation Home in Geneva

Spacious ‘GEM’ of the city
9.8 out of 10, Exceptional, (44 reviews)
"Enjoyed our stay in this spacious, comfortable house right in downtown Geneva. House was short walk to HWS, downtown restaurants, and lakefront/FLX visitor center. We would happily stay here again. "
United States
Lynda F.
$288 nightly
The price is $318
Jan 14 - Jan 15
Total with taxes and fees
Spacious ‘GEM’ of the city
Exterior
Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes

Cabin in Cohocton

Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes
10.0 out of 10, Exceptional, (19 reviews)
"Loved the cabin We had a great stay"
United States
Sue T.
$164 nightly
The price is $184
Jan 19 - Jan 20
Total with taxes and fees
Timber Haven - Serene log home getaway with Wi-Fi, HVAC in NY Finger Lakes
2 bedrooms, WiFi, bed sheets
The Johnson Chalet in Bristol/Canandaigua*HOT TUB*

Chalet in Canandaigua

The Johnson Chalet in Bristol/Canandaigua*HOT TUB*
10.0 out of 10, Exceptional, (5 reviews)
"Our stay was relaxing and very comfortable. The cottage is well appointed and upscale in its feel. And it's located in a verybprivate setting while still being close to major roads. We enjoyed our stay."
United States
Kip B.
$377 nightly
The price is $407
Jan 14 - Jan 15
Total with taxes and fees
The Johnson Chalet in Bristol/Canandaigua*HOT TUB*
Exterior
Pet Friendly Log Cabin

Vacation Home in Penn Yan

Pet Friendly Log Cabin
9.4 out of 10, Exceptional, (55 reviews)
"Very Clean, Peaceful and serene, enjoyed our time here. "
United States
Alisha W.
$146 nightly
The price is $151
Feb 9 - Feb 10
Total with taxes and fees
Pet Friendly Log Cabin
Smart TV, fireplace
Hubbs Cellar at JS Hubbs Guest House

Condo in Hammondsport

Hubbs Cellar at JS Hubbs Guest House
10.0 out of 10, Exceptional, (7 reviews)
"Clean, modern, great host, and walking distance to a beautiful water view. So nice!"
United States
Jonathan S.
$230 nightly
The price is $257
Jan 14 - Jan 15
Total with taxes and fees
Hubbs Cellar at JS Hubbs Guest House
Property grounds
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!

Cottage in Penn Yan

1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!
3.0 star property
9.8 out of 10, Exceptional, (81 reviews)
"Great location, water front property, close to wineries, dining and entertainment. "
United States
Jay M.
$344 nightly
The price is $385
Jan 31 - Feb 1
Total with taxes and fees
1 bed/ba lakeside cottage, large deck, west side of Seneca Lake. Pet Friendly!
Interior
A dreamy Seneca Lake retreat with sweeping views, a relaxing hot tub under the stars, flexible bedroom setups, a fully stocked kitchen, cozy living spaces, and easy access to the lake, wineries, and waterfalls.

Vacation Home in Romulus

A dreamy Seneca Lake retreat with sweeping views, a relaxing hot tub under the stars, flexible bedroom setups, a fully stocked kitchen, cozy living spaces, and easy access to the lake, wineries, and waterfalls.
10.0 out of 10, Exceptional, (10 reviews)
"Place was clean and check in was easy. Host was very responsive and helpful and there were a lot of suggestions for local places for us to browse through. Will definitely be looking to stay again next time we visit the Finger Lakes"
United States
Christa
$292 nightly
The price is $325
Jan 14 - Jan 15
Total with taxes and fees
A dreamy Seneca Lake retreat with sweeping views, a relaxing hot tub under the stars, flexible bedroom setups, a fully stocked kitchen, cozy living spaces, and easy access to the lake, wineries, and waterfalls.
TV, fireplace
Lake Trout Cove Summa

Vacation Home in Canandaigua

Lake Trout Cove Summa
2.0 star property
$390 nightly
The price is $393
Jan 14 - Jan 15
Total with taxes and fees
Lake Trout Cove Summa
Interior
Charming Rustic Cabin #5 near canal

Cabin in Waterloo

Charming Rustic Cabin #5 near canal
10.0 out of 10, Exceptional, (1 review)
"Great communication and very nice place "
United States
Andi K.
$169 nightly
The price is $188
Jan 15 - Jan 16
Total with taxes and fees
Charming Rustic Cabin #5 near canal
Fridge, microwave, oven, stovetop
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

Vacation Home in Canandaigua

The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
10.0 out of 10, Exceptional, (80 reviews)
"This is the second time I’ve stayed here, great experience both times."
United States
Deanna S.
$288 nightly
The price is $310
Jan 14 - Jan 15
Total with taxes and fees
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Fridge, oven, stovetop, coffee/tea maker
Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!

Vacation Home in Penn Yan

Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!
10.0 out of 10, Exceptional, (3 reviews)
"It was cozy and welcoming, owner was prompt answering any questions"
United States
Andrew M.
$260 nightly
The price is $291
Jan 14 - Jan 15
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

The Lake House on Canandaigua

The Lake House on Canandaigua

10/10 Excellent
"Beautiful comfortable room with view of the woods and lake outlet"
Linda 1-night trip
Posted 2 days ago
The Lake House on Canandaigua

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 $184 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?

Keuka East: Spacious & Comfy: This vacation home rental outside of Middlesex is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Middlesex?

Choose from 13 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.