Middlesex Holiday Rentals from AU$148: 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

12 Nov - 13 Nov

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

2. Savannah Safari Tent & Breakfast-FLX Glamping

Rushville

Faithann B.

includes taxes & fees

12 Nov - 13 Nov

A yurt with a central skylight, a bed with a 'OFFLINE' sign, a woven chair, and a patterned rug.

3. 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

12 Nov - 13 Nov

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

Rushville

ERIC W.

includes taxes & fees

2 Nov - 3 Nov

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

5. Ideal location for adventure all year round

Naples

Andrew A.

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with two Adirondack chairs, a stone wall, and a view of a lake and distant mountains.

6. Lakefront Canandaigua Home w/ Grill, Fire Pit

Canandaigua

A.G.A. N.

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.

7. Beautiful Tiny home Near The Lake

Canandaigua

includes taxes & fees

10 Nov - 11 Nov

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

8. Finger Lakes Cottage

Prattsburgh

Jessica W.

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Top Middlesex Hotel Reviews

Hampton Inn Penn Yan

10/10 Excellent

"The hotel location is perfect, overlooking the lake. Best to reserve a lake view room."

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."

Showboat Hotel

10/10 Excellent

"If you want a clean room with a great view this is the place. The room is not luxurious but it is comfortable. There is no daily room service or food service but there is a restaurant on the property open for lunch and dinner most days. There are bins with some essentials like coffee, toilet paper, and extra towels outside of the front office. The maids are around during the day and are helpful if there is a problem or if you need anything. We've booked two stays there and plan to return."

The Lake House on Canandaigua

8/10 Good

"The property and rooms are absolutely stunning, think upscale, boutique Nantucket vibes with pockets of ‘old money’ feels. Everything was clean, the lobby and each ‘cabin’ smells phenomenal. The kind of trip you take and think, ‘wow I need to work harder so I can come to places like this more often’. Highly recommend renting their free bikes and biking down the street to their quaint ‘downtown area’, check out Patty’s place for an at home/diner style breakfast. Perfect quiet location just 30 minutes from the busier winery areas. 10/10 would come again, very romantic and breathtaking setting."

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, 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 favourite 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 depend 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 AU$148 per night. Entering your travel dates in the search wizard might find you 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. Savannah Safari Tent & Breakfast-FLX Glamping

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

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

5. Ideal location for adventure all year round

6. Lakefront Canandaigua Home w/ Grill, Fire Pit

7. Beautiful Tiny home Near The Lake

8. Finger Lakes Cottage

9. VRFLX Canandaigua View | Pool & Hot Tub

10. Finger Lakes Escape • FLX Chalet + Private Pond

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

12. Sub Level Effiency

13. Escape to the Heart of the Finger Lakes

14. Pet Friendly Keuka Yurt

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

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

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

18. Cozy, rustic cabin with beautiful views, privacy and 1 mile from Keuka Lake

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

Find holiday rentals that suit your style

Top Middlesex Hotel Reviews

Hampton Inn Penn Yan

Plum Point Lodge

Americas Best Value Inn Farmington

Holiday Inn Express & Suites Geneva Finger Lakes by IHG

Best Western Plus Vineyard Inn & Suites

Microtel by Wyndham Penn Yan Finger Lakes Region

Days Inn by Wyndham Geneva/Finger Lakes

Showboat Hotel

The Lake House on Canandaigua

Find out more about Middlesex

Frequently asked questions

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