Middlebury holiday lettings

We found 94 holiday rentals — enter your dates for availability

Discover a selection of 12 homes and other holiday rentals in Middlebury that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the amenities that you need and want, such as Wi-Fi and cable TV. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Why people love visiting historical Middlebury

Come and experience Middlebury and its architecture, cathedral and history. This scenic city is known for its university setting, riverfront and waterfalls. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Middlebury

Are you searching for attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes Middlebury a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Sugarbush Ski Resort (16 mi / 25.8 km)
  • Rikert Nordic Center (9.7 mi / 15.6 km)
  • Gunnison Lakeshore Orchards (14 mi / 22.6 km)
  • Mad River Glen Cooperative (17.5 mi / 28.2 km)
  • Blueberry Lake Cross Country and Snowshoeing Center (17.9 mi / 28.8 km)
  • Lincoln Peak Vineyard (2.9 mi / 4.7 km)

Exploring the natural features in Middlebury

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Middlebury. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Dunmore (9 mi / 14.5 km)
  • Chimney Point State Historic Site (12.7 mi / 20.4 km)
  • Otter Creek (15.5 mi / 24.9 km)
  • Moss Glen Falls (15.8 mi / 25.4 km)
  • Warren Falls (16 mi / 25.8 km)
  • Mad River Valley (16.4 mi / 26.4 km)

Travelling to and around Middlebury

The nearest airport is in Burlington, VT (BTV-Burlington Intl.), located 31.4 mi (50.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Montpelier, VT (MPV-Edward F. Knapp State), which is 32.7 mi (52.7 km) away.

Frequently asked questions

What is the best area to stay in Middlebury when booking a holiday rental?
When considering a holiday rental in Middlebury, Vermont, a popular area to stay is the charming downtown district. This vibrant neighbourhood boasts a delightful mix of historic architecture, boutique shops, and a variety of eateries, making it great for those who enjoy a lively atmosphere. You'll find yourself within walking distance of top attractions such as the Middlebury College campus, which not only offers beautiful grounds to explore but also hosts numerous cultural events throughout the year. Additionally, the nearby Otter Creek is a lovely spot for leisurely strolls or picnics, providing a serene backdrop to your holiday experience.

Another excellent option is the area surrounding the Middlebury Natural Foods Co-op. This region is particularly appealing for those who appreciate local produce and organic offerings. With several properties available, you can easily find a comfortable place to unwind after a day of exploring. Nearby, the Henry Sheldon Museum of Vermont History offers an engaging glimpse into the region's past, making it a worthwhile visit for history enthusiasts.
How much does it cost to rent a holiday home in Middlebury?
Prices for holiday rentals in Middlebury vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Middlebury to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Middlebury holiday house rentals?
You can find great discounts on house rentals in Middlebury on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Middlebury ski resort rentals?
For the best ski resort rentals near Middlebury, Vermont, travellers should focus on the areas surrounding the Middlebury Snow Bowl, which is just a short drive away. In the town of Middlebury itself, you can find a range of rental properties, including cosy cabins and modern apartments that cater to various group sizes. Many of these accommodations come with amenities such as fully equipped kitchens, comfortable living areas, and some even feature fireplaces, great for unwinding after a day on the slopes.

Additionally, the nearby towns of Bristol and Weybridge offer further options, with charming country homes and lodges set against a picturesque backdrop of the Green Mountains. These properties often provide easy access to local eateries and shops, enhancing the overall experience for visitors. Many rentals in these areas also include outdoor spaces, ideal for enjoying the fresh mountain air, and some may even have hot tubs for a relaxing soak.
What is the most popular type of holiday rental accomodation in Middlebury?
In Middlebury, holiday houses are the most popular choice, with approximately 13 available throughout the area. These properties often come with multiple bedrooms, fully equipped kitchens, and spacious living areas, making them suitable for families or groups. Many holiday houses feature outdoor spaces, such as gardens or patios, where guests can relax and enjoy the scenic views of Vermont's countryside. Additionally, there are several apartments available, which provide a more compact and convenient option for travellers looking to explore the charming downtown area and its local attractions, including the Middlebury College campus and the beautiful Otter Creek.
Are there any family house rentals in Middlebury?
In Middlebury, Vermont, there are about 15 family-friendly house rentals available, making it an excellent choice for travellers seeking a home away from home. This charming town offers a variety of properties, often featuring spacious living areas, full kitchens for family meals, and outdoor spaces where children can play. Many homes also provide amenities like Wi-Fi and heating, ensuring a comfortable stay throughout the year.
Can I find long-stay holiday rentals in Middlebury?
A long-stay holiday rental in Middlebury is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Middlebury?
In Middlebury, there are several pet-friendly house rentals available, offering a variety of amenities suited for travellers with furry companions. Many of these properties feature spacious yards, allowing pets to roam freely, as well as modern kitchens and comfortable living areas for relaxation after a day of exploration.
Are there any remote work holiday rentals in Middlebury?
In Middlebury, Vermont, there are numerous remote work holiday rentals available, with around 18 properties catering specifically to the needs of remote workers. These rentals often feature dedicated workspaces, which include desks, desk chairs, and even office setups, making it convenient for those who need to focus on their tasks. Many properties also provide Wi-Fi, ensuring a reliable internet connection for video calls and online work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middlebury holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Middlebury with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Middlebury?
In Middlebury, popular rental amenities include essential features such as kitchens equipped with dishwashers and microwaves, allowing guests to prepare their own meals. Many rooms also provide cookware, dishware, and utensils, making it convenient for travellers to dine in. Additionally, free Wi-Fi is commonly available in rooms, ensuring that guests stay connected during their stay.
How early should I book a Middlebury holiday rental?
Book your Middlebury holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middlebury?
In Middlebury, visitors can explore a charming blend of historical and natural attractions. The Middlebury College campus is a significant point of interest, featuring beautiful architecture and the renowned Middlebury College Museum of Art, which showcases a diverse collection of artwork.

The Otter Creek, which runs through the town, offers picturesque views and opportunities for outdoor activities such as kayaking and fishing. Nearby, the picturesque Bread Loaf area is famous for its scenic landscapes and hiking trails, making it a great spot for nature lovers.
Can I change or cancel my Middlebury home rental booking on Vrbo?
To find Middlebury holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Middlebury holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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