Middlesex Holiday Rentals from NZ$159: 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

Jessica F.

includes taxes & fees

1 Dec - 2 Dec

A spacious wooden interior with large windows, a central dining table, and a chandelier.

2. VRFLX Canandaigua View | Pool & Hot Tub

Naples

"Our stay was absolutely wonderful! We loved the spectacular views, the pool, hot tub & the spacious inside. Our family was able to make wonderful dinners, because the kitchen was stocked with all items we needed. I can’t say enough about the hosts. They were wonderful & very accommodating. Communication was so easy! We were very sad to leave, so therefore, we are so looking forward to coming back."

Trudy Z.

includes taxes & fees

16 Nov - 17 Nov

A spacious living area with a fireplace, a large flat-screen TV, and a cozy seating arrangement.

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

Naples

includes taxes & fees

16 Nov - 17 Nov

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

4. Savannah Safari Tent & Breakfast-FLX Glamping

Rushville

Faithann B.

includes taxes & fees

15 Dec - 16 Dec

A covered outdoor patio with a table and chairs, a sofa, and a view of a garden.

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

Canandaigua

Corey P.

includes taxes & fees

15 Nov - 16 Nov

A modern cabin with a large deck, a covered outdoor seating area, and a staircase leading to the main entrance.

6. Finger Lakes Escape • FLX Chalet + Private Pond

Branchport

Catherine K.

includes taxes & fees

22 Nov - 23 Nov

A lakeside patio with outdoor seating and a fire pit.

7. The Vita and Vine: Lakefront, Outdoor Theater

Rushville

includes taxes & fees

17 Nov - 18 Nov

8. Ideal location for adventure all year round

Naples

Andrew A.

includes taxes & fees

18 Nov - 19 Nov

A wooden deck with a fire feature, a pergola, and a view of trees and hills.

9. Wine Country: Epic Game Room, Lake Views, Fire Pit

Naples

Maffettone Thiesmeyer T.

includes taxes & fees

16 Nov - 17 Nov

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

Rushville

Tamara B.

includes taxes & fees

19 Nov - 20 Nov

A wooden dock extending into a body of water, with a building and greenery in the background.

11. Nov 13-15 Christkindl/Murder Mystery wknd, Pets Same day bookings ok terms apply

Canandaigua

Charlie M.

includes taxes & fees

15 Nov - 16 Nov

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

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

Naples

Graham B.

includes taxes & fees

29 Nov - 30 Nov

A modern kitchen with a central island, wooden chairs, and green cabinetry.

13. Charming country ranch in the hills of the Finger Lakes

Naples

Brian K.

includes taxes & fees

26 Nov - 27 Nov

A waterfront property with a dock, a house with a deck, and a large tree.

14. Lakeside Home - We accept direct same day bookings w VRBO booking;2 pets welcome

Canandaigua

Christopher H.

includes taxes & fees

30 Nov - 1 Dec

A spacious room with a high ceiling, wooden beams, a large rug, exercise equipment, and a small kitchenette.

15. Private Backyard & Deck · Family-Friendly

Penn Yan

Emily W.

includes taxes & fees

16 Nov - 17 Nov

A kitchen with a stainless steel stove, oven, and a range hood above.

16. Entire Home - 4 Bedroom - Sleeps 10 Canandaigua - Steps Off Main St / Downtown

Canandaigua

Kelly D.

includes taxes & fees

16 Nov - 17 Nov

A fire pit surrounded by Adirondack chairs in a wooded area with a small pond and a covered structure in the background.

17. 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 Dec - 16 Dec

A modern kitchen with a wooden island, bar stools, a microwave, and a stove.

18. The Cozy Nest

Naples

Sean J.

includes taxes & fees

15 Dec - 16 Dec

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.

19. Escape to the Heart of the Finger Lakes

Naples

Anonymous traveller

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a balcony, large windows, and a stone pathway leading to outdoor seating.

20. Enjoy Cabin Vibes & Lake Views, Close to Town, Lake & FLX Activities; EV Charger

Canandaigua

"We had a wonderful stay at this beautiful home on Lake Canandaigua! The house was spotless, well-maintained, and had everything we needed for a relaxing and enjoyable vacation. We loved grilling out for BBQ dinners and spending the evenings around the fire pit making s’mores with the family. The lake views were absolutely stunning, and the location was perfect—close to everything while still feeling peaceful and private. We would definitely stay here again and highly recommend it!"

Wendy B.

includes taxes & fees

15 Nov - 16 Nov

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Find holiday rentals that suit your style

Top Middlesex Hotel Reviews

A grassy area with two Adirondack chairs, a picnic table, and a view of a lake with boats and a distant shoreline.

Hotel Canandaigua, Tapestry Collection by Hilton

Canandaigua

10/10 Excellent

Daryl

A multi-story hotel with a covered entrance, stone facade, and a parking area.

Microtel Inn & Suites by Wyndham Farmington

Farmington

10/10 Excellent

Timothy

A dining area with wooden tables and chairs, a bar area, and large windows providing natural light.

Comfort Inn & Suites Farmington - Victor

Farmington

10/10 Excellent

Ben

A hotel room with a fireplace, a round wooden table with a bottle of wine and glasses, a chair, and a bed with a black and white throw blanket.

Canandaigua Guesthouse

Canandaigua

10/10 Excellent

Loved it here! Valerie & Jason were wonderful hosts - so welcoming and relaxed. Breakfasts were delicious and winding down at the end of the day with a glass of wine was so nice in the comfy lounge/dining area. We really enjoyed meeting them and their home was beautiful inside and out. Modern amenities blended with classic features made it very comfortable for our three night stay. Thanks for having us!

Amelia

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 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 NZ$159 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.

Middlesex Holiday Rentals

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. VRFLX Canandaigua View | Pool & Hot Tub

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

4. Savannah Safari Tent & Breakfast-FLX Glamping

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

6. Finger Lakes Escape • FLX Chalet + Private Pond

7. The Vita and Vine: Lakefront, Outdoor Theater

8. Ideal location for adventure all year round

9. Wine Country: Epic Game Room, Lake Views, Fire Pit

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

11. Nov 13-15 Christkindl/Murder Mystery wknd, Pets Same day bookings ok terms apply

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

13. Charming country ranch in the hills of the Finger Lakes

14. Lakeside Home - We accept direct same day bookings w VRBO booking;2 pets welcome

15. Private Backyard & Deck · Family-Friendly

16. Entire Home - 4 Bedroom - Sleeps 10 Canandaigua - Steps Off Main St / Downtown

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

18. The Cozy Nest

19. Escape to the Heart of the Finger Lakes

20. Enjoy Cabin Vibes & Lake Views, Close to Town, Lake & FLX Activities; EV Charger

Find holiday rentals that suit your style

Top Middlesex Hotel Reviews

Hotel Canandaigua, Tapestry Collection by Hilton

10/10 Excellent

Find out more about Middlesex

Middlesex holiday rentals: An excellent choice for every season

How to find incredible deals on Middlesex rentals

Frequently Asked Questions

Are there holiday rentals in Middlesex?

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

How many holiday rentals will I find in Middlesex?

What can I see and do in Middlesex?

What are holiday rentals like in Middlesex?