Middlesex holiday lettings

We found 906 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Middlesex to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Middlesex

Showing deals for:14 Nov - 21 Nov
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Find out more about Middlesex

Find out more about Middlesex

Why visit Middlesex

  • Stunning outdoor activities: Middlesex is perfect for skiing and hiking, set amid picturesque landscapes ideal for nature lovers.
  • Historic charm: Explore the village's historic bridges and sites that showcase the area's rich heritage and culture.
  • Artistic exploration: Enjoy local galleries that highlight the vibrant art scene and creativity of the region.
  • Welcoming community: Experience the friendliness of locals who enhance your stay with their hospitality.
  • Varied accommodation options: Choose from charming cabins, stylish condos, or private holiday homes to suit your needs.

Popular types of accommodation in Middlesex

If you're looking for the perfect getaway in Middlesex, you're in the right place. Our most popular types of accommodation include houses, stylish condos, and cosy cabins. Whether you're interested in apartments, holiday rentals, or rented accommodation, we have a variety of options to suit your needs. For extended stays, check out our monthly rentals to make your time in Middlesex even more enjoyable.

  • Houses: The top choice for visitors in Middlesex, ideal for families or groups seeking a home-like atmosphere.
  • Condos: A popular option for those wanting a modern living space with hotel-like amenities.
  • Cabins: Perfect for nature lovers, offering a rustic retreat in a picturesque setting.
  • Apartments: A convenient choice for couples or solo travellers wanting easy access to local attractions.
  • Cottages: Charming and cosy, these are great for a more quaint and tranquil getaway.**

Top attractions near Middlesex

Middlesex, Vermont, offers a delightful mix of adventure and culture for visitors. Ideal for outdoor and ski holidays, it features captivating attractions such as national parks, historic bridges, and local galleries. Whether you're seeking thrilling outdoor experiences or a taste of local heritage, Middlesex caters to all types of travellers, making it a perfect destination for a memorable getaway.

  • Vermont State House: A stunning example of Greek Revival architecture, the Vermont State House is a historic government building that exudes cultural significance. Visitors can explore its beautiful grounds and learn about the state's political history, all while enjoying the vibrant atmosphere just 3.1km from Middlesex.
  • Norwich University: As the oldest private military college in the United States, Norwich University offers a unique glimpse into the history of military education. Its picturesque campus, located 6.8km away, features remarkable architecture and a rich cultural heritage.
  • Waterbury Center State Park: A haven for outdoor enthusiasts, Waterbury Center State Park is perfect for hiking, picnicking, and enjoying scenic views of the water. Located 4.3km from Middlesex, it provides a refreshing escape into nature.

Things to do recommended for couples

For a romantic getaway in Middlesex, explore Fresh Tracks Farm Vineyard and Winery for a delightful wine-tasting experience. Enjoy skiing together at Bolton Valley Ski Area or indulge in luxury at the Country Club of Vermont, creating unforgettable memories in a beautiful setting.

Things to do recommended for families

Families can indulge in sweet treats at the Ben and Jerry's Factory, a delightful spot just 3.1km from Middlesex. For a splash of fun, the Swimming Hole, located 8.1km away, offers a fantastic aquatic centre perfect for family enjoyment.

Things to do recommended for groups

Groups visiting Middlesex can enjoy local delights at Cold Hollow Cider Mill, just 3.7km away, savour performances at Lost Nation Theater, also 3.7km away, or experience the thrill of motor racing at Thunder Road International Speedbowl, located 7.5km from the town.

What do I need to keep in mind when booking a vacation in 'Middlesex

If you're travelling with a group, family, or pets, or if you're seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Middlesex with a group: Think about how many bedrooms you require, along with amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Middlesex with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Middlesex: For many families, a holiday wouldn’t feel complete without their beloved furry companion. If you can relate to this, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Middlesex: If you're seeking holiday rentals that offer great deals for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Middlesex

Middlesex, Vermont, offers a delightful blend of adventure and relaxation, ideal for outdoor enthusiasts and families alike. Explore the charming village and its scenic surroundings, perfect for skiing and hiking. Nearby, you can discover historical sites and enjoy excursions that reveal the area's rich heritage. With friendly locals and picturesque landscapes, your visit to Middlesex promises memorable experiences. Don't miss the chance to unwind in this lovely corner of New England.

  • Stowe: Nestled 7.5km from Middlesex, Stowe is renowned for its stunning natural beauty and outdoor adventures. This charming town is famous for its ski resorts, attracting winter sports enthusiasts from far and wide. Visitors can indulge in skiing, snowboarding, and cross-country skiing amidst the picturesque mountains. In the warmer months, Stowe transforms into a hub for hiking, mountain biking, and exploring the scenic valleys and lakes. Notable attractions include the iconic Stowe Mountain Resort and the tranquil Waterbury Reservoir, perfect for a day of relaxation and exploration.
  • Montpelier: Located a mere 3.7km from Middlesex, Montpelier is the capital of Vermont and offers a unique blend of outdoor adventures and cultural experiences. Known for its ski fields, the area draws thrill-seekers eager to hit the slopes during winter. Montpelier's vibrant downtown features charming shops, local eateries, and historic sites. Highlights include the stunning State House and various parks that showcase the beauty of the surrounding landscape, including the nearby mountains and lakes, making it an ideal spot for both adventure and relaxation.
  • Waterbury: Just 3.1km away from Middlesex, Waterbury is a delightful town that offers a wealth of outdoor activities and scenic vistas. Known for its adventure sports, Waterbury is a favourite among ski enthusiasts, with easy access to ski fields and resorts. The town is also home to the famous Ben & Jerry's Ice Cream Factory, where visitors can take guided tours and indulge in delicious treats. The nearby valley and mountain landscapes provide ample opportunities for hiking, biking, and enjoying the great outdoors, making Waterbury a perfect getaway for nature lovers.

Best time to go to Middlesex

If you're planning a trip to Middlesex, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January17.6°F (-8.0°C)Light RainMostly CloudyModerately LowSlightly High
February19.9°F (-6.7°C)Light RainMostly CloudyAverageSlightly High
March28.6°F (-1.9°C)Light RainMostly CloudyAverageAverage
April41.4°F (5.2°C)Light RainMostly CloudyAverageAverage
May55.4°F (13.0°C)Light RainMostly SunnyAverageSlightly Low
June62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly Low
July68.5°F (20.3°C)Light RainMostly SunnyModerately HighAverage
August66.6°F (19.2°C)Light RainMostly SunnyModerately HighAverage
September59.4°F (15.2°C)Light RainMostly SunnyModerately HighSlightly Low
October47.5°F (8.6°C)Light RainMostly CloudyAverageAverage
November34.7°F (1.5°C)Light RainMostly CloudyModerately LowAverage
December24.8°F (-4.0°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is simple

Are you keen to save on your next getaway? It’s worth considering some flexibility with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated area to plan new getaways, pick up from where you last stopped, or manage your travel arrangements. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Middlesex getaway

Learn about the unique charm of Middlesex with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Middlesex

Are you hoping to discover attractions to visit in the area? Venture out of your holiday home and check out everything that makes Middlesex a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Stowe Mountain Resort (17.3 mi / 27.8 km)
  • Ceres (5.3 mi / 8.6 km)
  • Cold Hollow Cider Mill (6.5 mi / 10.4 km)
  • Bolton Valley Ski Area (11.9 mi / 19.2 km)
  • Swimming Hole (12.5 mi / 20.2 km)
  • Mad River Glen Cooperative (13.8 mi / 22.3 km)

Exploring the natural landscape of Middlesex

Whether you're an adventurous traveller or just want to appreciate the scenery, Middlesex is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Little River State Park (8 mi / 12.9 km)
  • Mad River (13.8 mi / 22.2 km)
  • Mad River Valley (15.4 mi / 24.7 km)
  • Mount Mansfield Peak (18.6 mi / 29.9 km)
  • Osmore Pond (19.2 mi / 30.9 km)
  • Smugglers Notch (21.1 mi / 34 km)

Transport options to and around Middlesex

The nearest airport is in Montpelier, VT (MPV-Edward F. Knapp State), located 8.5 mi (13.6 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Stowe, VT (MVL-Morrisville-Stowe State), which is 17.2 mi (27.7 km) away.

Frequently asked questions

How much does it cost to rent a holiday rental in Middlesex?
Several things affect how much you'll pay for a holiday rental in Middlesex, like the type of property, length of stay and season. Still, all of our holiday homes have one thing in common — amazing value. Just enter your travel dates to find your dream escape.
How much does it cost to rent a beach house in Middlesex?
When you travel and the size and style of the property will influence the cost of your beachside holiday rental. Type in your Middlesex travel dates to see your options on Vrbo. Did someone just say "hot tub"? Use our filters to select the amenities and features you want.
What are the top attractions for families in Middlesex?
You'll find lots of wonderful things to do and see with the family in Middlesex, including:

  • Vermont Historical Society Museum
  • T.W. Wood Art Gallery
  • T.W. Wood Gallery

How old do you have to be to rent a holiday rental in Middlesex?
We recommend checking with the Middlesex holiday property you'd like on Vrbo as age restrictions vary. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental in Middlesex for?
The length of time you can book a holiday rental in Middlesex differs according to the property. Just enter your selected travel dates to display a list of options offering extended stays. With lots of creature comforts such as air conditioning and full kitchens, as well as some offering discounted weekly or monthly prices, you're sure to find the perfect place to call your home away from home in Middlesex.

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