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Our top choices for Middlesex holiday rentals

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.
The price is £357
includes taxes & fees
1 Dec - 2 Dec
Peaceful lake front home with amazing views.

2. Beautiful Tiny home Near The Lake

Beautiful Tiny home Near The Lake
Canandaigua
4.8 out of 10, (5 reviews)
The price is £48
includes taxes & fees
9 Nov - 10 Nov
Beautiful Tiny home Near The Lake

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.
The price is £77
includes taxes & fees
11 Nov - 12 Nov
Ideal location for adventure all year round

4. Sub Level Effiency

Sub Level Effiency
Geneva
8.6 out of 10, Excellent, (22 reviews)
"A great place to stay "
United States
Patrick
The price is £79
includes taxes & fees
9 Nov - 10 Nov
Sub Level Effiency

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.
The price is £175
includes taxes & fees
19 Nov - 20 Nov
Beautiful Newly Renovated 1900s Farm House On 9 Acres

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 traveller
The price is £192
includes taxes & fees
10 Nov - 11 Nov
Escape to the Heart of the Finger Lakes

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.
The price is £180
includes taxes & fees
9 Nov - 10 Nov
Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

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
The price is £150
includes taxes & fees
7 Dec - 8 Dec
Pet Friendly Keuka Yurt

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.
The price is £192
includes taxes & fees
10 Nov - 11 Nov
Savannah Safari Tent & Breakfast-FLX Glamping

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.
Modern Studio - Main St Penn Yan

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.
The price is £322
includes taxes & fees
22 Nov - 23 Nov
Finger Lakes Escape • FLX Chalet + Private Pond

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.
The price is £224
includes taxes & fees
9 Nov - 10 Nov
The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

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
The price is £401
includes taxes & fees
16 Nov - 17 Nov
Naples Oasis: 2 bedrooms, 2 baths, a full kitchen and open-concept, lake views!

14. VRFLX Canandaigua View | Pool & Hot Tub

VRFLX Canandaigua View | Pool & Hot Tub
Naples
10.0 out of 10, Exceptional, (104 reviews)
"We traveled with family and our infant. It was a beautiful home and property. "
United States
Marina V.
The price is £476
includes taxes & fees
9 Nov - 10 Nov
VRFLX Canandaigua View | Pool & Hot Tub

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.
The price is £138
includes taxes & fees
10 Nov - 11 Nov
The Geneva Getaway- remodeled apartment walking distance from downtown Geneva

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.
The price is £412
includes taxes & fees
17 Nov - 18 Nov
Spacious Keuka Lake Gem, BBQ, Firepit, Gameroom

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)
The price is £193
includes taxes & fees
10 Nov - 11 Nov
Cozy tiny home with Sunrise Views in the Heart of Finger Lakes

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

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.
The price is £503
includes taxes & fees
9 Nov - 10 Nov
Canandaigua Lake Overlook | Hot Tub, Gazebo & Lake Views

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.
The price is £198
includes taxes & fees
9 Nov - 10 Nov
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

Find out more about Middlesex

Everything you need to know about Middlesex holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlesex holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesex holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesex holiday rentals we have selected for you start as low as £48 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex holiday 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 holiday.

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 holiday rentals in Middlesex?

Yes, there are holiday rentals close to the most popular sights in Middlesex, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middlesex has to offer?

Romantic Cottage-Breathtakng View-Beach Fire Pit!-Aval Sep-Oct'26-Now Booking'27: This holiday home rental outside Middlesex is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Middlesex?

Choose from 11 Expedia holiday rentals in Middlesex for a memorable holiday.

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 wider area, you’ll find West River Marsh and Bristol Mountain Ski Resort.

What are holiday rentals like in Middlesex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlesex. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.