Photo by Matthew Jay

Middlesex holiday rentals

We found 510 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Middlesex that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Middlesex

Showing deals for:13 Nov - 20 Nov

driveway to upper barn parking to left and 2 spaces opposite barn; 5 cars total
waterfront view; upper patio for owner
dining room detail
front porch lake view sunny
Exceptional
(40 reviews)

Canandaigua Lake Farmhouse

Canandaigua

7% off
AU$8,430
for 7 nights, 1 home
AU$1,204 per night
includes taxes & fees
Canandaigua Lake Farmhouse
coat hooks in garage entry
Spacious living room
View of kitchen from living room
Enjoy the campfire
Exceptional
(197 reviews)

Friends And Family Farmhouse

Penn Yan

8% off
AU$5,702
for 7 nights, 1 home
AU$815 per night
includes taxes & fees
Friends And Family Farmhouse
bathroom down
Southside porch
bedroom down east facing
1.9 acres with dock, house view to cottage
Exceptional
(5 reviews)

Charming 4-bedroom house with WiFi and AC in Branchport

Branchport

8% off
AU$9,773
for 7 nights, 1 home
AU$1,396 per night
includes taxes & fees
Charming 4-bedroom house with WiFi and AC in Branchport
Sunroom w/gas fireplace
View from Maids Quarters
Banquet hall
Koi Pond Sitting Area
Exceptional
(29 reviews)

Secluded European Style 1810 Mansion minutes to the lake, sleeps 15

Canandaigua

8% off
AU$12,012
for 7 nights, 1 home
AU$1,716 per night
includes taxes & fees
Secluded European Style 1810 Mansion minutes to the lake, sleeps 15
Primary suite (upstairs): King Bed, Smart TV, Closet, Ceiling Fan, Ensuite Bath
Our porch is a great spot to enjoy  morning coffee with views of Keuka Lake!
Enjoy the outdoors with pool, hot tub, grill, and outdoor dining area 💕
Take in views of Keuka Lake while enjoying our Solo Stove Fire Pit and seating
Exceptional
(28 reviews)

Lakeview w/Pool, Hot Tub, Firepit, Gameroom, Golf!

Penn Yan

8% off
AU$7,328
for 7 nights, 1 home
AU$1,047 per night
includes taxes & fees
Lakeview w/Pool, Hot Tub, Firepit, Gameroom, Golf!
Downstairs bedroom
View from the living room
Overhead view of the living room
3 seasons sun room
Exceptional
(167 reviews)

Chalet overlooking Keuka Lake in the heart of Wine Country

Penn Yan

15% off
AU$1,812
for 7 nights, 1 chalet
AU$259 per night
includes taxes & fees
Chalet overlooking Keuka Lake in the heart of Wine Country
Living area
Exterior
Private kitchen
Living area
Exceptional
(12 reviews)

Lake House Retreat on Beautiful Canandaigua Lake Sleeps 12

Middlesex

8% off
AU$12,680
for 7 nights, 1 cottage
AU$1,811 per night
includes taxes & fees
Lake House Retreat on Beautiful Canandaigua Lake Sleeps 12
Living area
Property grounds
Private kitchen
Several wineries nearby!
Exceptional
(47 reviews)

Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23

Penn Yan

8% off
AU$4,819
for 7 nights, 1 home
AU$688 per night
includes taxes & fees
Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23
Living area
Living area
Living area
Private kitchen
Exceptional
(458 reviews)

A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake

Penn Yan

8% off
AU$2,543
for 7 nights, 1 cabin
AU$363 per night
includes taxes & fees
A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake
Dining
Private kitchen
Exterior
Living area
Exceptional
(11 reviews)

Beautiful and Secluded getaway on 10 acres

Canandaigua

8% off
AU$5,172
for 7 nights, 1 home
AU$739 per night
includes taxes & fees
Beautiful and Secluded getaway on 10 acres
Information binder on island to help guest enjoy their stay.
Interior
Grill on back deck for outdoor cooking.
Fully stocked kitchen
Exceptional
(147 reviews)

Newly Renovated Rustic Cabin w/WiFi in the Heart of the Finger Lakes

Branchport

8% off
AU$1,072
for 7 nights, 1 cabin
AU$153 per night
includes taxes & fees
Newly Renovated Rustic Cabin w/WiFi in the Heart of the Finger Lakes
Private kitchen
Living area
Dining
Private kitchen
Exceptional
(39 reviews)

Beautifully Renovated Lodge with Lakeview

Canandaigua

12% off
AU$4,004
for 7 nights, 1 home
AU$572 per night
includes taxes & fees
Beautifully Renovated Lodge with Lakeview
Kitchen
Livingroom
Dining Room
Front Yard
Exceptional
(36 reviews)

Tranquil Lodge with A+ Amenities

Naples

8% off
AU$4,200
for 7 nights, 1 home
AU$600 per night
includes taxes & fees
Tranquil Lodge with A+ Amenities
Record room
Kitchen with lake views
Living room
Master bedroom
Exceptional
(22 reviews)

Renovated Spacious Canandaigua Lake House with Hot Tub and Sauna

Canandaigua

8% off
AU$9,093
for 7 nights, 1 home
AU$1,299 per night
includes taxes & fees
Renovated Spacious Canandaigua Lake House with Hot Tub and Sauna
Exterior
Exterior
Living area
Living area
Excellent
(13 reviews)

Spacious home with private lake front

Canandaigua

8% off
AU$4,286
for 7 nights, 1 home
AU$612 per night
includes taxes & fees
Spacious home with private lake front
Exterior
Dining Table converts to Pool Table
Living area
Interior
Exceptional
(100 reviews)

VRFLX Canandaigua View | Pool & Hot Tub

Naples

6% off
AU$5,139
for 7 nights, 1 home
AU$734 per night
includes taxes & fees
VRFLX Canandaigua View | Pool & Hot Tub
Bedroom 2 with Queen Bed
View from Covered Patio
Eat-In Kitchen
Eat-In Kitchen with Views of Lake
Exceptional
(66 reviews)

Remodeled Lake House

Honeoye

8% off
AU$1,954
for 7 nights, 1 cottage
AU$279 per night
includes taxes & fees
Remodeled Lake House
Property grounds
Outdoor dining
Living area
Living area
Exceptional
(10 reviews)

Robust vacation home near wineries, nature and ski mountains in the FLX region!

Naples

8% off
AU$4,534
for 7 nights, 1 home
AU$648 per night
includes taxes & fees
Robust vacation home near wineries, nature and ski mountains in the FLX region!
Private kitchen
Balcony off of living room
Entrance across the street to the road that takes you to the community center
Interior
Exceptional
(37 reviews)

Waterfront two story condo

Canandaigua

8% off
AU$3,897
for 7 nights, 1 apartment
AU$557 per night
includes taxes & fees
Waterfront two story condo
view of house near Canandaigua Lake
Kitchen Area with stainless appliances.
Eat-in Kitchen
Lower level.
Exceptional
(12 reviews)

"Come Sail Away" A charming place in Canandaigua designed with a sailing theme.

Canandaigua

10% off
AU$2,937
for 7 nights, 1 home
AU$420 per night
includes taxes & fees
"Come Sail Away" A charming place in Canandaigua designed with a sailing theme.
Front of House
A Short Walk to the Water and Dock
Eat-In Kitchen
Enclosed Porch Showing View of Lake at End of Street
Exceptional
(111 reviews)

Remodeled House...Steps away from Honeoye Lake

Honeoye

8% off
AU$1,954
for 7 nights, 1 home
AU$279 per night
includes taxes & fees
Remodeled House...Steps away from Honeoye Lake
Large spacious couch in living room.
Large living room with 18’ ceiling.
Open floor plan in living room and kitchen.
Room
Exceptional
(54 reviews)

Renovated Cabin, with custom craftwork, in Picturesque Finger Lakes Wine Country

Branchport

8% off
AU$1,276
for 7 nights, 1 cabin
AU$182 per night
includes taxes & fees
Renovated Cabin, with custom craftwork, in Picturesque Finger Lakes Wine Country
Room
Outdoor dining
Aerial view
Exterior
Exceptional
(34 reviews)

Lakeside Studio Apartment steps from lake. Private Beach and Park

Honeoye

8% off
AU$1,125
for 7 nights, 1 apartment
AU$161 per night
includes taxes & fees
Lakeside Studio Apartment steps from lake. Private Beach and Park
Private kitchen
Property grounds
Exterior detail
Room
Exceptional
(23 reviews)

Tranquil creek side retreat

Canandaigua

8% off
AU$1,320
for 7 nights, 1 apartment
AU$189 per night
includes taxes & fees
Tranquil creek side retreat
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Explore the natural setting in Middlesex

Learn about the unique charm of Middlesex with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Middlesex

Are you hoping to discover attractions to see while you're in town? Venture out of your cosy holiday rental and check out everything that Middlesex has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bristol Mountain Ski Resort (7.5 mi / 12 km)
  • Roseland Waterpark (12.2 mi / 19.6 km)
  • Fox Run Vineyards (15.5 mi / 25 km)
  • Ravines Wine Cellars on Seneca Lake (16.9 mi / 27.3 km)
  • Keuka Lake Vineyards (19.3 mi / 31.1 km)
  • Bully Hill Vineyards (19.4 mi / 31.2 km)

Exploring the natural features in Middlesex

Whether you're an active traveller or just want to appreciate the scenery, Middlesex is a great place to spend some time outside. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Canandaigua Lake (5.4 mi / 8.7 km)
  • Keuka Lake State Park (11 mi / 17.8 km)
  • Honeoye Lake (12.8 mi / 20.7 km)
  • Sonnenberg Gardens and Mansion State Historic Park (13.3 mi / 21.4 km)
  • Keuka Lake Outlet Trail (14.2 mi / 22.8 km)
  • Keuka Lake (16.2 mi / 26 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Middlesex?
According to our research, houses are the most desirable holiday property type in Middlesex. But having said that, everyone's idea of an awesome stay isn't going to be the same. Stayz has holiday homes in a variety of sizes and shapes, and we'll help you locate the perfect fit.
How much does it cost to rent a holiday home in Middlesex?
Length of stay, season and property type are among the factors that can determine the price of a holiday home. Simply add your travel dates to find your ideal escape. From cosy country cottages to expansive villas, all Stayz holiday homes provide incredible value.
How much does it cost to rent a beach house in Middlesex?
Prices for beach houses in Middlesex differ depending on the size and type of the property and when you're travelling. All you have to do is enter your travel dates into Stayz and the number of guests to view holiday home options and prices. From there you can use the filters to tailor your search results by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday homes in Middlesex?
Pack a travel bag and a bone for the pooch in your life because Middlesex has 14 stays that open their doors to pets. Let your four-legged buddy join in on the family trip at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.
What are popular home amenities in Middlesex?
The most popular home amenities people are searching for in Middlesex are a water view, a firepit and a fireplace. Whether you're hitting the road with family, friends or even pets, Stayz holiday properties include the best amenities for starting a new adventure with the people who matter most.
Are there large group holiday homes in Middlesex?
Choose from seven holiday properties in Middlesex that can accommodate 10 or more guests. Whether you're organising a trip with the family or a special event, there's plenty of space to get your loved ones together under one roof.
Are there holiday homes in Middlesex that welcome kids?
With 14 family-friendly holiday homes to choose from in Middlesex, now is an awesome time to introduce the kids to the thrills of travel. Just check our "Properties good for families" filter to search for stays loaded with amenities ideal for holidaying families, like dining rooms, backyards, hot tubs and bunk beds.
What are the top attractions for families in Middlesex?
Keeping the kiddos entertained during your Middlesex holiday is a breeze with these top family-friendly attractions:
  • Conklin Gully
  • Clarks Gully
  • Bristol Mountain Ski Resort
Are there one-bedroom holiday homes in Middlesex?
You can choose from two one-bedroom homes in Middlesex. Whether you're on the lookout for a cosy chalet or a cabin, our one-bedroom properties are great if you don't need a lot of space. One of the best parts about having your own digs? You won't ever have to share your holiday with strangers.
Can I find two-bedroom holiday homes in Middlesex?
Middlesex has three two-bedroom properties that you can choose from. Experience a holiday home with all the comfort and privacy you want at a price that won't break the bank on Stayz.
Are there holiday homes with WiFi in Middlesex?
Whether you want to stay in touch with the news, make a video call or surf social media, there are six holiday homes with WiFi in Middlesex. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in Middlesex?
Middlesex has 14 holiday homes where you'll be able to relax and recharge in air-conditioned comfort. To locate a property on Stayz that provides this amenity, enter your travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Middlesex?
The minimum age permitted can differ between properties on Stayz, so look at the rules of the holiday home in Middlesex you're considering. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Middlesex for?
It all depends on the Middlesex property. To browse a list of options offering extended stays, just type your dates and guest number into the Stayz search page. You can enjoy having the entire place to yourself, along with home comforts like a fully-equipped kitchen, air conditioning and a backyard where the kids can burn off energy. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.