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Middlebury vacation rentals

We found 100 vacation rentals — enter your dates for availability

Discover a selection of 13 homes and other vacation rentals in Middlebury that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Middlebury

Why visit Middlebury

  • Outdoor Adventures: Middlebury is perfect for outdoor enthusiasts with activities like skiing and hiking in its stunning landscapes.
  • Historic Charm: Explore the vibrant downtown area filled with quaint shops, cafes, and rich history.
  • Middlebury College: Visit this prestigious college known for its beautiful campus and cultural events.
  • Scenic Lakes: Enjoy peaceful retreats at nearby lakes, ideal for relaxation and family-friendly activities.
  • Diverse Accommodations: Choose from cozy condos, charming cabins, or private vacation homes for a perfect stay.

Popular types of accommodation in Middlebury

If you're looking for the perfect getaway in Middlebury, you'll find a variety of accommodation options to suit your needs. Our most popular types of vacation rentals include houses, cozy condos, and charming cabins. Whether you're interested in monthly rentals, a downtown apartment, or a home in the heart of Vermont, we have the ideal place for you to relax and enjoy your stay.

  • Houses: The top choice for visitors, these homes offer spacious accommodations perfect for families or groups looking to enjoy a home-like atmosphere during their stay in Middlebury.
  • Condos: A popular option for those seeking a blend of comfort and amenities, condos provide convenient access to local attractions and activities.
  • Cabins: Rustic and charming, cabins offer a cozy retreat in nature, ideal for those wanting a peaceful getaway.
  • Cottages: Quaint and inviting, cottages are perfect for couples or small families wanting a charming escape.
  • Apartments: Offering a convenient and flexible option, apartments are well-suited for solo travelers or those on shorter stays.**

Top attractions in Middlebury

Middlebury, Vermont, is perfect for outdoor and adventure vacations, offering a variety of attractions such as parks, historic sites, and scenic lakes. Visitors can explore Middlebury College, enjoy alpine skiing, and find family-friendly experiences. The area also boasts excellent hotels and a service marina for those seeking additional activities. With its rich culture and stunning landscapes, Middlebury promises unforgettable adventures for all types of travelers.

  • Kevin P. Mahaney '84 Center for the Arts: This vibrant arts center showcases a diverse range of performances and exhibitions, fostering a deep appreciation for the arts within the community. Visitors can enjoy music, theater, and visual arts in a welcoming atmosphere.
  • National Museum of the Morgan Horse: Dedicated to the beloved Morgan horse breed, this museum features engaging exhibits that highlight the history and significance of these remarkable animals. It's a must-visit for equine enthusiasts and history buffs alike.
  • Henry Sheldon Museum of Vermont History: This museum offers a fascinating glimpse into Vermont's past through its extensive collections and exhibits. Visitors can explore local artifacts and stories that bring the region's history to life.

Things to do recommended for couples

Middlebury offers charming experiences for couples. Explore the scenic trails along Lake Dunmore or enjoy a wine tasting at a local vineyard. Don’t miss a leisurely stroll through the picturesque downtown, filled with quaint shops and cozy cafes, perfect for a romantic afternoon together.

Things to do recommended for families

Families can explore the scenic trails at the Middlebury College Snow Bowl, enjoy hands-on exhibits at the Middlebury Science Center, or take a stroll along the picturesque Otter Creek. Don’t miss the interactive activities at the Vermont Folklife Center for a unique cultural experience.

Things to do recommended for groups

In Middlebury, groups can enjoy a scenic hike at the beautiful Bread Loaf Mountain, visit the historic Middlebury College campus, and explore the charming downtown shops and eateries. Don't miss the chance to tour the local cheese factory for a delicious tasting experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, with family, bringing pets, or planning an extended stay, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Middlebury with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Middlebury with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to attractions that are enjoyable for the whole family.
  • Taking your pets with you to Middlebury: For many families, a vacation wouldn't be the same without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Middlebury: If you're searching for vacation rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a spacious kitchen, or a private pool in your search.

Where to stay in and around Middlebury

Middlebury, Vermont, offers a charming blend of historical and scenic experiences perfect for outdoor enthusiasts. Explore the vibrant downtown area, where friendly locals greet you amidst quaint shops and cafes. Venture into the nearby rural landscapes for peaceful retreats and adventure-filled activities, from skiing to hiking. Discover the unique vibe of Middlebury and its surrounding regions, where relaxation and adventure go hand in hand, making your vacation an unforgettable experience.

  • Cornwall: Nestled near the picturesque town of Middlebury, Cornwall is a charming village that captivates visitors with its stunning outdoor scenery and romantic ambiance. Travelers flock to Cornwall for its abundant opportunities to explore nature, from serene lakes to majestic mountains. Popular activities include skiing at nearby resorts, making it an ideal destination for winter sports enthusiasts. Visitors can also immerse themselves in the local history with a trip to the historic college university. Cornwall is perfect for those seeking a tranquil escape while enjoying the beauty of Vermont's landscape.
  • Weybridge: A quaint village close to Middlebury, Weybridge is known for its inviting outdoor spaces and romantic settings. This charming locale offers a delightful mix of activities, including access to scenic lakes and urban parks, making it ideal for leisurely strolls and picnics. Cultural enthusiasts will appreciate the local theater and shopping center, providing a taste of Vermont's vibrant community. With its stunning views and intimate atmosphere, Weybridge is a must-visit for travelers looking to unwind and experience the essence of small-town Vermont.
  • Middlebury - Warren: Located a mere 0.7 miles from Middlebury, Middlebury - Warren is a thrilling destination for adventure seekers and outdoor enthusiasts. Renowned for its exceptional skiing opportunities, this area boasts several ski resorts and fields that attract winter sports lovers year-round. Beyond skiing, visitors can explore the captivating landscapes featuring lakes and mountains. Event conference venues also add to the area's appeal, making it a versatile spot for both recreation and gatherings. With its stunning backdrop and adventure-filled activities, Middlebury - Warren offers an unforgettable experience for all.

Best time to go to Middlebury

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.2°F (-7.1°C)Light RainMostly CloudyAverageSlightly High
February21.4°F (-5.9°C)Light RainMostly CloudyModerately HighSlightly High
March29.8°F (-1.2°C)Light RainMostly CloudyAverageAverage
April42.4°F (5.8°C)Light RainMostly CloudyModerately LowSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyModerately LowAverage
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnyModerately HighAverage
August67.8°F (19.9°C)Light RainMostly SunnyModerately HighAverage
September60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly Low
October48.4°F (9.1°C)Light RainMostly CloudyAverageAverage
November35.6°F (2.0°C)Light RainMostly CloudyModerately LowSlightly Low
December26.8°F (-2.9°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Also, extending your stay can lead to substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your travel needs.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for you to plan new trips, manage your existing plans, and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting historic 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 vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Middlebury

Do you want to discover things to do in the area? Venture out of your vacation home and experience everything that makes Middlebury a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Neshobe Golf Club (14.5 mi / 23.3 km)
  • Sugarbush Ski Resort (16 mi / 25.8 km)
  • Otter Valley Winery (16.5 mi / 26.5 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 an adventurous traveler or just want to take in the scenery, Middlebury is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Cornwall Swamp Wildlife Management Area (6.3 mi / 10.1 km)
  • Lake Dunmore (9 mi / 14.5 km)
  • Chimney Point State Historic Site (12.7 mi / 20.4 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)

Traveling to and around Middlebury

The nearest airport is in Burlington Intl. Airport (BTV), located 31.4 mi (50.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly 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, Vermont, United States of America when booking a vacation rental?
When considering a vacation rental in Middlebury, Vermont, the downtown area is an excellent choice. This vibrant neighborhood not only offers a charming small-town atmosphere but also provides easy access to a variety of shops, restaurants, and local cafes. Staying downtown places you near the picturesque Otter Creek, superb for leisurely strolls or picnics, and the Middlebury College campus, which features beautiful architecture and lovely green spaces.

Another appealing area is the neighborhoods surrounding the Middlebury River, where you can find a mix of cozy homes and quaint rentals. This area is close to the Middlebury Natural Foods Co-op, a great spot to explore local produce and products. Additionally, the nearby Middlebury College Museum of Art is a fantastic attraction that showcases a diverse collection of artwork and hosts various events throughout the year.
How much does it cost to rent a vacation home in Middlebury?
Prices for vacation 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 vacation 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, travelers should consider accommodations in the charming town of Middlebury itself as well as the nearby area of Bristol. Middlebury offers a variety of rental options, including cozy cabins and spacious homes, many of which feature amenities such as fully equipped kitchens, fireplaces, and outdoor spaces for enjoying the picturesque Vermont landscapes.

In Bristol, which is just a short drive from the Middlebury Snow Bowl ski area, visitors can find rustic chalets and modern condos. These properties often come with conveniences like hot tubs, ski storage, and proximity to local dining and shopping options. The community atmosphere in Bristol enhances the experience, with local events and a friendly vibe.

Additionally, the ski areas around Middlebury, including the Middlebury Snow Bowl, provide great access to winter sports, while the surrounding Green Mountains offer stunning views and outdoor activities year-round.
What is the most popular type of vacation rental accomodation in Middlebury?
In Middlebury, vacation houses are the most popular type of rental, with about 11 available throughout the area. These homes typically offer multiple bedrooms, fully equipped kitchens, and spacious living areas, ideal for families or groups looking to enjoy the charm of this Vermont town. Many of these houses are situated near local attractions such as the Middlebury College campus and the picturesque Otter Creek, providing a superb base for exploring the area. Additionally, there are several apartments available, which also cater to travelers seeking a homely atmosphere, often featuring convenient amenities for a comfortable stay.
Are there any family house rentals in Middlebury?
In Middlebury, Vermont, there are some family-friendly house rentals available, with around 14 options to choose from. This charming town offers a great mix of outdoor activities and cultural experiences, making it an ideal destination for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play freely.

Visitors will appreciate amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay. The town is home to beautiful parks and recreational areas, providing opportunities for hiking, biking, and enjoying nature. Additionally, the vibrant downtown area boasts local shops, cafes, and the renowned Middlebury College, adding to the cultural richness of the locale.
Can I find long-stay vacation rentals in Middlebury?
A long-stay vacation rental in Middlebury is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Middlebury?
In Middlebury, Vermont, there are several pet-friendly house rentals available for travelers looking to enjoy the picturesque surroundings of this charming town. Many vacation homes in the area come equipped with amenities such as fully stocked kitchens, cozy living spaces, and outdoor decks or patios, making them ideal for families and groups traveling with pets.

The town's location offers easy access to beautiful parks and outdoor spaces, great for pet walks and exploration. For example, the nearby Otter Creek State Forest provides trails and scenic spots where pets are welcome, allowing for enjoyable outdoor adventures. Additionally, the vibrant downtown area features pet-friendly cafes and shops, enhancing the overall experience for those traveling with their furry companions. See all pet-friendly rentals in Middlebury.
Are there any remote work vacation rentals in Middlebury?
In Middlebury, Vermont, there are several remote work vacation rentals available, with around 14 options to choose from. This charming town, known for its picturesque landscapes and vibrant cultural scene, offers accommodations that cater to remote workers. Many properties come equipped with essential amenities such as reliable Wi-Fi, comfortable workspaces, and often a peaceful environment conducive to productivity.

Travelers can find rentals featuring cozy living areas, fully equipped kitchens for meal preparation, and sometimes outdoor spaces for relaxation during breaks. The proximity to local attractions, including the beautiful Middlebury College campus and the scenic surrounding areas, adds to the appeal of working remotely in this delightful setting. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middlebury vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middlebury with parking available—perfect for families or travelers 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 vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals and enjoy the convenience of home cooking. Many rentals also feature decks or patios, providing outdoor spaces to relax and take in the fresh Vermont air. Onsite parking is commonly available, making it easy for guests to arrive and explore the surrounding area without hassle. Additionally, some units offer porches or lanais, great for enjoying morning coffee or evening sunsets. Blenders are also a common amenity, suiting those who enjoy making smoothies or other blended drinks during their stay.
When is the best time to visit Middlebury for a vacation rental?
The best time to visit Middlebury for a vacation rental is during the enchanting month of September. This period marks the peak season, running from July to September, when visitors flock to experience the gorgeous landscapes and vibrant culture of Vermont. September offers a delightful climate with temperatures typically ranging from the mid-50s to mid-70s Fahrenheit, creating superb conditions for outdoor activities and sightseeing.

As the summer crowds begin to wane, September provides an ideal balance of pleasant weather and fewer tourists. You can enjoy the stunning fall foliage that starts to emerge, making it a picturesque time for hiking or leisurely strolls along the scenic trails. Middlebury's charming downtown area, with its boutique shops and cafes, is also a wonderful place to explore without the hustle and bustle of peak tourist traffic.

If you're looking for a more budget-friendly option, consider visiting in November. While it's a quieter month, it offers a unique chance to experience the tranquility of the area before winter sets in. The early winter landscape can be quite beautiful, and there are often local events and festivals to enjoy.

Ultimately, your ideal time to visit Middlebury will depend on whether you prefer the lively option of late summer or the peaceful charm of the shoulder months.
How early should I book a Middlebury vacation rental?
Book your Middlebury vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middlebury, Vermont, United States of America?
In Middlebury, visitors can explore a charming blend of history and natural beauty. The Middlebury College campus is a significant draw, featuring beautiful architecture and the Henry Sheldon Museum, which showcases local history and culture. The vibrant downtown area offers a variety of shops and restaurants, making it a great spot for leisurely strolls and dining experiences.

Just a short drive away, the scenic Otter Creek provides opportunities for kayaking and fishing, while nearby hiking trails in the Green Mountains offer stunning views of the fall foliage. The Middlebury River is also popular for its picturesque landscapes and is ideal for nature lovers.
Can I change or cancel my Middlebury home rental booking on Vrbo?
To find Middlebury vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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