Middlebury holiday lettings

We found 101 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.

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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)
  • Mad River Glen Cooperative (17.5 mi / 28.2 km)
  • Blueberry Lake Cross Country and Snowshoeing Center (17.9 mi / 28.8 km)
  • Ole's Cross Country Center (18.4 mi / 29.5 km)
  • Ticondroga Country Club (19.2 mi / 30.9 km)
  • Charlotte Village Winery (19.9 mi / 32 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)
  • Vergennes Falls Park (11.5 mi / 18.5 km)
  • Chimney Point State Historic Site (12.7 mi / 20.4 km)
  • Texas Falls Recreation Area (14.5 mi / 23.3 km)
  • Moss Glen Falls (15.8 mi / 25.4 km)
  • Warren Falls (16 mi / 25.8 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, the downtown area is an excellent choice. This vibrant neighbourhood not only offers a charming small-town atmosphere but also provides easy access to a variety of attractions. The picturesque Middlebury College is located here, giving visitors the opportunity to explore beautiful campus grounds and attend cultural events throughout the year. Additionally, the nearby Otter Creek offers lovely spots for a leisurely stroll or a picnic alongside the water.Another appealing area is the surrounding countryside, which showcases the stunning natural beauty of Vermont. Renting a property here allows you to immerse yourself in the scenic landscapes, with opportunities for hiking, biking, and enjoying the famous autumn foliage. The proximity to attractions like the Henry Sheldon Museum of Vermont History adds an enriching cultural experience to your stay.While the downtown area features a selection of properties that cater to various preferences, the countryside offers a more tranquil setting, great for those looking to unwind.
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, travellers should focus on the charming town of Middlebury itself and the nearby areas of Bristol and Weybridge. Middlebury offers a variety of accommodations, including cosy chalets and rustic cabins that are superb for families or groups looking to enjoy the slopes. Many of these properties come equipped with amenities such as fully equipped kitchens, wood-burning stoves, and spacious living areas, ideal for relaxing after a day on the mountain.In Bristol, which is just a short drive from Middlebury, visitors can find a selection of delightful cottages and homes that often feature scenic views of the surrounding mountains. Some properties include outdoor decks, hot tubs, and access to hiking trails, providing a superb blend of winter sports and outdoor adventure. Weybridge also offers a more rural setting, with lovely farmhouses and cabins that have been updated for comfort while retaining their charming character. These accommodations frequently have amenities like fireplaces, large dining areas, and proximity to local attractions.Additionally, the nearby Middlebury College Snow Bowl offers excellent skiing opportunities, with rentals conveniently located for easy access to the slopes. After a day of skiing, guests can explore the delightful local restaurants and shops in Middlebury, making it a vibrant base for a winter getaway.
What is the most popular type of holiday rental accomodation in Middlebury?
In Middlebury, holiday houses are the most popular type of holiday rental, with about 44 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or groups. Additionally, there are around 16 apartments scattered throughout the town, offering a more compact option for those looking for a cosy stay. Most apartments come with essential amenities such as kitchen facilities and comfortable living areas, providing a convenient base for exploring the charming downtown or visiting local attractions like the Middlebury College campus and the beautiful Otter Creek.
Are there any family house rentals in Middlebury?
In Middlebury, Vermont, there are numerous family-friendly holiday rentals available, with around 14 options to choose from. This charming town offers a delightful blend of outdoor activities and cultural experiences, making it an excellent choice for families. Many properties feature spacious living areas, fully equipped kitchens great for family meals, and outdoor spaces where children can play or relax.Visitors will find accommodations close to local attractions such as the Middlebury College campus, where families can enjoy cultural events and concerts, as well as the beautiful Otter Creek, ideal for picnicking and nature walks. The surrounding landscape offers opportunities for hiking and exploring, ensuring that there's something for everyone in the family to enjoy.
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 that cater to families and groups looking for a comfortable stay. Many of these properties come equipped with modern amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces, great for enjoying the beautiful Vermont scenery.The town itself offers a charming atmosphere, with easy access to local shops, cafes, and cultural sites such as the Middlebury College Museum of Art. For those who enjoy the outdoors, the surrounding area is rich with opportunities for hiking, biking, and exploring the picturesque landscapes that Vermont is renowned for. The nearby Otter Creek offers lovely spots for leisurely walks, making it a great option for guests with pets.
Are there any remote work holiday rentals in Middlebury?
In Middlebury, Vermont, there are numerous holiday rentals suitable for remote work, with around 56 options available. This charming town, known for its picturesque landscapes and vibrant college atmosphere, offers a variety of properties that cater to those needing a conducive work environment. Many rentals feature high-speed Wi-Fi, dedicated workspaces with desks and comfortable chairs, ensuring that guests can maintain productivity during their stay.Additionally, properties often come with amenities such as fully equipped kitchens, allowing for convenient meal preparation, and spacious living areas to relax after a day of work. The proximity to local coffee shops and the scenic beauty of the surrounding area provide excellent opportunities for breaks and inspiration. 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 well-equipped kitchens, which allow guests to prepare their own meals, and spacious decks or patios where they can relax and enjoy the fresh air. Onsite parking is another common feature, making it convenient for those travelling by car. Many rentals also offer inviting porches or lanais, superb for enjoying the scenic surroundings. Additionally, some properties come equipped with blenders, ideal for guests who enjoy making smoothies or other blended drinks during their stay.
When is the best time to visit Middlebury for a holiday rental?
September is the best time to visit Middlebury for a holiday rental, as it captures the tail end of the vibrant summer season and welcomes the colourful onset of autumn. This month typically features mild temperatures, ranging from around 10 to 20 degrees Celsius, creating a friendly space for outdoor activities and sightseeing.During the peak season from July to September, Middlebury thrives with tourists eager to explore its charming downtown, local festivals, and the stunning landscapes of the surrounding Green Mountains. September, in particular, offers the great blend of pleasant weather and fewer crowds, allowing you to fully appreciate the beauty of the fall foliage as it begins to transform the landscape.For those seeking a more budget-friendly option, November presents an excellent opportunity to experience Middlebury in a quieter setting. While the leaves may have fallen, the crisp air and serene surroundings make it ideal for peaceful walks along the trails or exploring the local arts scene.Ultimately, whether you are drawn to the lively summer atmosphere or the tranquil beauty of late autumn, Middlebury has something to offer every type of traveller.
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 enjoy a variety of attractions that showcase the charm of this picturesque New England town. The Middlebury College campus is a highlight, featuring beautiful architecture and the renowned Middlebury College Museum of Art, which houses a diverse collection of artworks. The town's historic downtown area offers quaint shops, local cafes, and a vibrant arts scene, making it ideal for leisurely strolls.Outdoor enthusiasts can explore the nearby Bread Loaf Wilderness Area, which offers hiking trails with stunning views, particularly in the autumn when the foliage is at its most spectacular. Additionally, the Otter Creek, which runs through the town, provides opportunities for fishing and kayaking, making it a great spot for those who enjoy water activities.For a slice of local history, the Henry Sheldon Museum of Vermont History offers insights into the region's past, while the nearby Middlebury Falls presents a scenic spot for photography and relaxation.
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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