Middlesex Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Middlesex vacation rentals

A room with a large window overlooking a body of water, wicker furniture, and a patterned rug.

1. Peaceful lake front home with amazing views.

Peaceful lake front home with amazing views.
Middlesex
10.0 out of 10, Exceptional, (27 reviews)
"Very quiet and peaceful when we were there ."
United States
Julie Z.
$427 nightly
The price is $479
Dec 1 - Dec 2
Total with taxes and fees
Peaceful lake front home with amazing views.
A modern kitchen with a stainless steel refrigerator, microwave, and stove, a bar area with stools, and a sliding glass door leading to a backyard with a barbecue grill.

2. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
4.8 out of 10, (5 reviews)
$57 nightly
The price is $61
Nov 8 - Nov 9
Total with taxes and fees
Beautiful Tiny home Near The Lake
A living room with a sectional sofa, a fireplace, and a large window.

3. Ideal location for adventure all year round

Ideal location for adventure all year round
Naples
10.0 out of 10, Exceptional, (9 reviews)
"The space was perfectly clean, comfortable, and convenient. I would definitely stay here again!"
United States
Andrew A.
$93 nightly
The price is $100
Nov 11 - Nov 12
Total with taxes and fees
Ideal location for adventure all year round
A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

4. Sub Level Effiency

Sub Level Effiency
Geneva
9.0 out of 10, Wonderful, (21 reviews)
"A great place to stay "
United States
Patrick
$87 nightly
The price is $96
Nov 6 - Nov 7
Total with taxes and fees
Sub Level Effiency
Living area

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

Beautiful Newly Renovated 1900s Farm House On 9 Acres
Rushville
8.0 out of 10, Very good, (3 reviews)
"Property was an eclectic mix of old and new. Great location! Very comfortable. Will definitely consider staying there again."
United States
Tamara B.
$207 nightly
The price is $232
Nov 15 - Nov 16
Total with taxes and fees
Beautiful Newly Renovated 1900s Farm House On 9 Acres
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.

6. Escape to the Heart of the Finger Lakes

Escape to the Heart of the Finger Lakes
Naples
10.0 out of 10, Exceptional, (4 reviews)
"I enjoyed my stay. The host left a nice welcome card was very easy to communicate with."
United States
Anonymous traveler
$250 nightly
The price is $269
Nov 11 - Nov 12
Total with taxes and fees
Escape to the Heart of the Finger Lakes
A yurt with a central skylight, a bed with a 'OFFLINE' sign, a woven chair, and a patterned rug.

7. 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.
$210 nightly
The price is $235
Nov 6 - Nov 7
Total with taxes and fees
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region
A yurt interior with a round ceiling, a mounted television, a wooden barrel, and a small kitchenette.

8. Pet Friendly Keuka Yurt

Pet Friendly Keuka Yurt
Penn Yan
9.6 out of 10, Exceptional, (30 reviews)
"Such a fun yurt and a peaceful location! We loved the proximity to activities and then relaxing with a glass of wine on the little balcony!"
United States
Sharon
$207 nightly
The price is $209
Dec 1 - Dec 2
Total with taxes and fees
Pet Friendly Keuka Yurt
A group of Adirondack chairs arranged around a fire pit in a forested area with a small cabin in the background.

9. 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.
$237 nightly
The price is $265
Nov 6 - Nov 7
Total with taxes and fees
Savannah Safari Tent & Breakfast-FLX Glamping
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)
"Great place downtown over looking Main Street. I really liked the decor and the apartment was fully equiped with everything we needed. Greta coffee place across the street with amazing croissants for breakfast."
United States
Aki S.
$225 nightly
The price is $227
Nov 10 - Nov 11
Total with taxes and fees
Modern Studio - Main St Penn Yan
A modern living room with a green sofa, a wooden floor, and a large sliding glass door leading to an outdoor deck with chairs and a table.

11. Finger Lakes Escape • FLX Chalet + Private Pond

Finger Lakes Escape • FLX Chalet + Private Pond
Branchport
10.0 out of 10, Exceptional, (11 reviews)
"Great place for a winter getaway!"
United States
Catherine K.
$386 nightly
The price is $426
Nov 22 - Nov 23
Total with taxes and fees
Finger Lakes Escape • FLX Chalet + Private Pond
A kitchen with wooden cabinets, a microwave, and a dining table with woven placemats.

12. The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
Canandaigua
10.0 out of 10, Exceptional, (89 reviews)
"Everything you need, very nice base for exploring the finger lakes."
United States
Adam R.
$275 nightly
The price is $296
Nov 8 - Nov 9
Total with taxes and fees
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!
A spacious living area with a fireplace, a large flat-screen TV, and a cozy seating arrangement.

13. Naples Oasis: 2 bedrooms, 2 baths, a full kitchen and open-concept, lake views!

Naples Oasis: 2 bedrooms, 2 baths, a full kitchen and open-concept, lake views!
Naples
$559 nightly
The price is $601
Nov 16 - Nov 17
Total with taxes and fees
Naples Oasis: 2 bedrooms, 2 baths, a full kitchen and open-concept, lake views!
A spacious wooden interior with large windows, a central dining table, and a chandelier.

14. VRFLX Canandaigua View | Pool & Hot Tub

VRFLX Canandaigua View | Pool & Hot Tub
Naples
10.0 out of 10, Exceptional, (103 reviews)
"We traveled with family and our infant. It was a beautiful home and property. "
United States
Marina V.
$592 nightly
The price is $637
Nov 9 - Nov 10
Total with taxes and fees
VRFLX Canandaigua View | Pool & Hot Tub
A modern living room with a sliding barn door, a gray armchair, a wooden coffee table, and a gray sofa with patterned throw blankets.

15. The Geneva Getaway- remodeled apartment walking distance from downtown Geneva

The Geneva Getaway- remodeled apartment walking distance from downtown Geneva
Geneva
10.0 out of 10, Exceptional, (33 reviews)
"Great stay. Had all we needed!"
United States
Melissa N.
$164 nightly
The price is $181
Nov 10 - Nov 11
Total with taxes and fees
The Geneva Getaway- remodeled apartment walking distance from downtown Geneva
A single-story house with a porch, surrounded by a well-maintained lawn and trees with autumn foliage.

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

Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom
Penn Yan
10.0 out of 10, Exceptional, (8 reviews)
"We love the area. The house was very clean and had fun activities for us to do while there!"
United States
Renee S.
$477 nightly
The price is $534
Dec 1 - Dec 2
Total with taxes and fees
Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom
A compact kitchen with a sink, stove, and wooden cabinets.

17. Cozy tiny home with Sunrise Views in the Heart of Finger Lakes

Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
Penn Yan
10.0 out of 10, Exceptional, (1 review)
$233 nightly
The price is $260
Nov 9 - Nov 10
Total with taxes and fees
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes
A spacious living room with a large wooden dining table, a blue sofa, and a fireplace.

18. 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, (26 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
$450 nightly
The price is $484
Nov 6 - Nov 7
Total with taxes and fees
Lakeview retreat with beach access. Stylish home just steps from Deep Run Beach.
A spacious living room with hardwood flooring, a ceiling fan, a large window with a view, and a leather couch.

19. Canandaigua Lake Overlook | Hot Tub, Gazebo & Lake Views

Canandaigua Lake Overlook | Hot Tub, Gazebo & Lake Views
Canandaigua
8.6 out of 10, Excellent, (7 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.
$628 nightly
The price is $672
Nov 9 - Nov 10
Total with taxes and fees
Canandaigua Lake Overlook | Hot Tub, Gazebo & Lake Views
A modern living room with a sectional sofa, a dining table with chairs, a kitchen area, and a large window with a view of trees.

20. Cozy 1BDR APT in Vibrant Downtown Geneva

Cozy 1BDR APT in Vibrant Downtown Geneva
Geneva
9.8 out of 10, Exceptional, (20 reviews)
"The apartment was adorable. Perfect place to stay for our needs. Ryan was great and very responsive to my emails. Would definitely stay here again!"
United States
Stacey L.
$242 nightly
The price is $261
Nov 8 - Nov 9
Total with taxes and fees
Cozy 1BDR APT in Vibrant Downtown Geneva
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

An outdoor patio with tables and chairs, overlooking a lake.
Hampton Inn Penn Yan

Hampton Inn Penn Yan

Hampton Inn Penn Yan
Penn Yan

10/10 Excellent

Beautiful by the lake. Pay the extra 10 or 20 dollars for the lake view rooms. Nice pool. Nice hot tub. Nice view. Nice deck. Nice gym. Nice people.
United States
Vincenzo
Reviewed July 20, 2024
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 $61 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.

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?

Romantic Cottage-Breathtakng View-Beach Fire Pit!-Aval Sep-Oct'26-Now Booking'27: This vacation home rental outside Middlesex is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation 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.

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