Photo by Matthew Jay

Middlesex holiday lettings

We found 494 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:3 Oct - 10 Oct

Image gallery for Finger Lakes Chalets – Pool is Open! Up the hill from Canandaigua Lake!

Pool is Open May 1st!
10 out of 10 rating
Exceptional
(5 reviews)

Finger Lakes Chalets – Pool is Open! Up the hill from Canandaigua Lake!

Canandaigua, NY

8% off
Price is £1,495
£214 per night
includes taxes & fees
Finger Lakes Chalets – Pool is Open! Up the hill from Canandaigua Lake!

Find spaces that suit your style

  • 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, 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)
  • Keuka Lake Vineyards (19.3 mi / 31.1 km)
  • Bully Hill Vineyards (19.4 mi / 31.2 km)
  • Three Brothers Wineries and Estates (19.6 mi / 31.5 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 rental 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. Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo and the number of guests to view holiday rental 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 rentals 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 rentals on Vrbo. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.
What are popular rental amenities in Middlesex?
The most popular rental 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, Vrbo holiday properties include the best amenities for starting a new adventure with the people who matter most.
Are there large group holiday rentals 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 rentals 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 rentals in Middlesex?
You can choose from two one-bedroom rentals 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 rentals 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 Vrbo.
Are there holiday rentals 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 Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Middlesex?
Middlesex has 14 holiday rentals where you'll be able to relax and recharge in air-conditioned comfort. To locate a property on Vrbo 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 rental in Middlesex?
The minimum age permitted can differ between properties on Vrbo, 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 rental 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 Vrbo 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.

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