Middlesex Holiday Rentals from €101: Search Short-Term Rentals

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Our top choices for Middlesex holiday rentals

A lakeside setting with Adirondack chairs and a blue crate on a stone-paved area.

1. Peaceful lake front home with amazing views.

Middlesex

Julie Z.

includes taxes & fees

15 Nov - 16 Nov

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

Canandaigua

includes taxes & fees

7 Nov - 8 Nov

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

Rushville

Tamara B.

includes taxes & fees

15 Nov - 16 Nov

A living room with a sectional sofa, a fireplace, and a large window.

4. Ideal location for adventure all year round

Naples

Andrew A.

includes taxes & fees

11 Nov - 12 Nov

A cozy cabin interior with a sectional sofa, wooden ceiling, white cabinets, and a kitchenette.

5. Finger Lakes Cottage

Prattsburgh

Jessica W.

A kitchen with a wooden table, two chairs, a microwave, and a brick wall.

6. Sub Level Effiency

Geneva

Patrick

includes taxes & fees

3 Nov - 4 Nov

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

Rushville

"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...

Stephanie M.

includes taxes & fees

15 Nov - 16 Nov

A group of Adirondack chairs arranged around a fire pit in a forested area with a small cabin in the background.

8. Savannah Safari Tent & Breakfast-FLX Glamping

Rushville

Faithann B.

includes taxes & fees

3 Nov - 4 Nov

A spacious living area with a kitchen, a sofa, and a dining table.

9. Modern Studio - Main St Penn Yan

Penn Yan

Aki S.

includes taxes & fees

10 Nov - 11 Nov

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.

10. Finger Lakes Escape • FLX Chalet + Private Pond

Branchport

Catherine K.

A modern living room with a sliding barn door, a gray armchair, a wooden coffee table, and a gray sofa with patterned throw blankets.

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

Geneva

Melissa N.

includes taxes & fees

3 Nov - 4 Nov

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.

12. Escape to the Heart of the Finger Lakes

Naples

Anonymous traveller

includes taxes & fees

3 Nov - 4 Nov

A kitchen with wooden cabinets, a microwave, and a dining table with woven placemats.

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

Canandaigua

Adam R.

includes taxes & fees

3 Nov - 4 Nov

A spacious living room with a large wooden dining table, a blue sofa, and a fireplace.

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

Canandaigua

John

includes taxes & fees

3 Nov - 4 Nov

A yurt interior with a round ceiling, a mounted television, a wooden barrel, and a small kitchenette.

15. Pet Friendly Keuka Yurt

Penn Yan

Sharon

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with a large island, a sink, and a window overlooking a yard.

16. Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!

Penn Yan

alan

includes taxes & fees

8 Nov - 9 Nov

A spacious cabin with a large dining area, kitchen, and seating space with a view of a lake.

17. NEW! Hot-Tub, Sauna, Game Rm, Firepit, Wineries, Mins to Bristol MTN Ski Resort.

Naples

Graham B.

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.

18. Cozy 1BDR APT in Vibrant Downtown Geneva

Geneva

Stacey L.

includes taxes & fees

4 Nov - 5 Nov

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

Corey P.

includes taxes & fees

3 Nov - 4 Nov

A compact kitchen with a sink, stove, and wooden cabinets.

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

Penn Yan

includes taxes & fees

3 Nov - 4 Nov

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Top Middlesex Hotel Reviews

Americas Best Value Inn Farmington

10/10 Excellent

"LOVE STAYING THERE VERY CLEAN , QUIT, GREAT PLACE TO RELAX , STAFF ALWAYS NICE , VERY COMFORTABLE EVERYTIME LOVE IT"

Plum Point Lodge

8/10 Good

"The air conditioning HVAC system is very loud when it kicks on. It makes a loud noise. Also, the bathrooms could use a refreshment, not necessarily a total makeover, but some improvements to refresh. Also, no coffee maker in the room by coffee is available in the lobby. The dark plum comforter on the bed is a nice touch maybe , but would prefer a lighter color as these dark colors can hide stains and what not."

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 €101 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.

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.

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Check prices for these dates

Our top choices for Middlesex holiday rentals

1. Peaceful lake front home with amazing views.

2. Beautiful Tiny home Near The Lake

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

4. Ideal location for adventure all year round

5. Finger Lakes Cottage

6. Sub Level Effiency

7. Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

8. Savannah Safari Tent & Breakfast-FLX Glamping

9. Modern Studio - Main St Penn Yan

10. Finger Lakes Escape • FLX Chalet + Private Pond

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

12. Escape to the Heart of the Finger Lakes

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

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

15. Pet Friendly Keuka Yurt

16. Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!

17. NEW! Hot-Tub, Sauna, Game Rm, Firepit, Wineries, Mins to Bristol MTN Ski Resort.

18. Cozy 1BDR APT in Vibrant Downtown Geneva

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

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

Find holiday rentals that suit your style

Top Middlesex Hotel Reviews

Americas Best Value Inn Farmington

Best Western Plus The Hammondsport Hotel

Comfort Inn & Suites Farmington - Victor

The Lake House on Canandaigua

Hampton Inn Penn Yan

Holiday Inn Express & Suites Geneva Finger Lakes by IHG

Fairfield Inn & Suites by Marriott Geneva Finger Lakes

Plum Point Lodge

Find out more about Middlesex

Frequently asked questions

Go further with the Expedia app

Holiday Rentals in Middlesex

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlesex holiday rentals

1. Peaceful lake front home with amazing views.

2. Beautiful Tiny home Near The Lake

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

4. Ideal location for adventure all year round

5. Finger Lakes Cottage

6. Sub Level Effiency

7. Achsah Mongolian Round Tent & Breakfast in Finger Lakes Wine Country region

8. Savannah Safari Tent & Breakfast-FLX Glamping

9. Modern Studio - Main St Penn Yan

10. Finger Lakes Escape • FLX Chalet + Private Pond

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

12. Escape to the Heart of the Finger Lakes

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

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

15. Pet Friendly Keuka Yurt

16. Cozy 1 Bed, 1 Bath Smart Home Capsule on Scenic Keuka Wine Trail–Modern Comfort!

17. NEW! Hot-Tub, Sauna, Game Rm, Firepit, Wineries, Mins to Bristol MTN Ski Resort.

18. Cozy 1BDR APT in Vibrant Downtown Geneva

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

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

Find holiday rentals that suit your style

Top Middlesex Hotel Reviews

Americas Best Value Inn Farmington

Find out more about Middlesex

Frequently asked questions

Go further with the Expedia app