Middlebury Accommodations

House

Mountain-view House ~ Mins To Middlebury, Flex Cancellation Policy

10.0

Exceptional

(32 Reviews)

2 Bedrooms 2 Baths 5 Guests

R7,584/Night 7 Nights - R53,084

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Bed & Breakfast

Swift House Inn

9.4

Exceptional

(48 Reviews)

8 Bedrooms 8 Baths 18 Guests 243.53 ft²

R4,334/Night 7 Nights - R30,343

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House

Purple Door Cottage in the heart of Middlebury!

2 Bedrooms 2 Baths 6 Guests 1500 ft²

R6,880/Night 7 Nights - R48,157

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Apartment

Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury

10.0

Exceptional

(21 Reviews)

2 Bedrooms 1 Bath 6 Guests

R12,406/Night 7 Nights - R86,836

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Bed & Breakfast

Cornwall Orchards Bed & Breakfast

8.0

Excellent

(18 Reviews)

4 Bedrooms 4 Baths 8 Guests 180.3 ft²

R2,855/Night 7 Nights - R19,984

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Apartment

Yurt in Middlebury, Vermont

10.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 2 Guests 314 ft²

R1,658/Night 7 Nights - R11,599

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Beautiful, well-appointed, 1-bedroom apt with gorgeous views

Highly Rated

Apartment

Beautiful, well-appointed, 1-bedroom apt with gorgeous views

9.8

Exceptional

(63 Reviews)

1 Bedroom 1 Bath 3 Guests

R3,157/Night 7 Nights - R22,105

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Apartment

*Downtown Middlebury Waterfall Studio Apartment*

9.8

Exceptional

(8 Reviews)

1 Bedroom 1 Bath 2 Guests

R5,819/Night 7 Nights - R40,734

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New

House

Purple Door Cottage in the heart of Middlebury!

2 Bedrooms 3 Baths 6 Guests 1500 ft²

R6,178/Night 7 Nights - R43,247

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House

Cozy Pleasant St Apartment in Downtown Middlebury!

3 Bedrooms 1 Bath 6 Guests

R3,817/Night 7 Nights - R26,721

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Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably

Highly Rated

House

Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably

10.0

Exceptional

(77 Reviews)

3 Bedrooms 2 Baths 8 Guests 2300 ft²

R8,589/Night 7 Nights - R60,131

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Custom Home just minutes from Middlebury

Highly Rated

House

Custom Home just minutes from Middlebury

10.0

Exceptional

(72 Reviews)

4 Bedrooms 2 Baths 6 Guests 3000 ft²

R7,994/Night 7 Nights - R55,955

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More Top-Rated Accommodations in Middlebury Area

Why Choose Rent By Owner for your Middlebury Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Middlebury

When should you plan your Accommodations stay?

Choosing the optimal time to visit this destination allows you to enjoy its unique seasonal charm and ensure a comfortable stay in Middlebury, Vermont, USA, making it easier to find the perfect accommodations through RentByOwner.com that suit your preferences and travel plans.

Peak Season Highlights

Late Summer to Early Fall (August to October)

During this period, you can experience the region at its most vibrant with colorful foliage and pleasant weather, making it an ideal time to enjoy the scenic beauty while exploring the local area.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 50°F to 55°F

Winter Holidays (December to February)

The winter season transforms the area into a winter wonderland, offering snowy landscapes perfect for cozy getaways and winter sports enthusiasts seeking a memorable stay.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 10°F to 15°F

Off-Season Highlights

Spring (April to May)

As the region awakens from winter, spring offers milder temperatures and blooming scenery, providing a peaceful ambiance for your visit without the peak crowds.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 35°F to 45°F

Early Summer (June)

Early summer welcomes fewer visitors before the midsummer rush, allowing you to enjoy the area's natural tranquility and lush landscapes comfortably.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 50°F to 55°F

Weekly Weather Forecast for Middlebury

How to Book Your Middlebury Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Middlebury

More Top-Rated Accommodations in Middlebury Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy access to spacious outdoor areas perfect for relaxing or family gatherings
Take advantage of private gardens or landscaped yards suited for outdoor dining and leisure
Benefit from nearby scenic hiking trails that showcase the region's natural beauty
Make use of outdoor fire pits or fireplaces for cozy evenings under the stars
Utilize outdoor seating and patio furniture to unwind after a day of exploring
Discover the convenience of outdoor recreational facilities like tennis courts or playgrounds
Experience the tranquility of scenic views and open spaces typical of the area's countryside

Top Attractions Around Middlebury

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities, including hiking, biking, and exploring local parks, all just moments from your stay in Middlebury.

Family Activities

Otter Creek Animal Land Engage your family with an interactive visit to this local farm where children can meet various farm animals in a safe and friendly environment.
Middlesex Community Center Enjoy a variety of family-friendly activities and indoor recreation options designed to keep everyone entertained regardless of the weather outside.
The Powers House Museum Explore the history of the area through engaging exhibits that offer educational fun for all ages, making it a great cultural outing for your family trip.
Middlebury Falls Discover the natural beauty of the region while taking a scenic walk along the falls, perfect for family photos and enjoying the outdoors together.

Adult Activities

Visit the Middlebury College Museum of Art: Explore this cultural hub that showcases impressive collections and offers a enriching experience for art enthusiasts in the region.
Hike the Robert Frost Trail: Take a scenic walk along this popular trail that features beautiful natural landscapes and peaceful surroundings, ideal for outdoor enthusiasts staying nearby.
Enjoy local wines and craft beers: Discover the area's vibrant brewing scene at local breweries and wineries, perfect for an adults-only tasting experience.
Explore downtown Middlebury: Wander through charming shops, dine at cozy restaurants, and soak up the welcoming atmosphere in the heart of this destination.

Other Places to Stay in Middlebury, VT

Middlebury - Warren

Explore 454 Properties

Addison County

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Halpin Covered Bridge

Explore 56 Properties

Cornwall

Explore 51 Properties

Middlebury College

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Kevin P. Mahaney '84 Center for the Arts

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Porter Medical Center

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UVM Health Network - Porter Medical Center

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Porter Hospital

Explore 33 Properties

Holy Cow Inc.

Explore 32 Properties

National Museum of the Morgan Horse

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Town Hall Theater

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More Places to Stay Near Middlebury

Middlebury Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead for Local Events: Check the area’s events calendar to align your stay with local festivals or seasons, enhancing your experience in Middlebury, Vermont.
Explore Scenic Routes: Take advantage of the region’s picturesque drives and outdoor trails to truly immerse yourself in the natural beauty surrounding your accommodations.
Sample Regional Cuisine: Discover local eateries and farm-to-table restaurants to enjoy authentic flavors that highlight the essence of Vermont.
Choose a Prime Location: Select an accommodation situated near key attractions or outdoor activities to maximize your time and convenience during your visit.

Transportation Options

Vermont Transit This regional bus service offers convenient routes connecting you to nearby cities and towns in the area, ideal for exploring without the need for a car.
Middlebury College Transit The local shuttle system provides free transportation around the college campus and surrounding neighborhoods, making short commutes easy during your stay.
Rental Cars Numerous rental car agencies are available nearby, giving you the flexibility to explore this picturesque region at your own pace.
Taxi and Ride-Sharing Services Reliable taxi services and ride-sharing options like Uber and Lyft operate here, providing quick and comfortable transportation within the local community.

Local Customs Options

Town Meeting Day: Participating in the annual town meeting reflects the strong sense of community and local governance that is cherished here.
Maple Syrup Traditions: Celebrating sugar-on-snow and other maple syrup customs highlights the region's rich maple sugaring heritage during the spring season.
Artisan Craftsmanship: Supporting local artisans through craft fairs and markets showcases the area's appreciation for handcrafted goods and regional artistry.
Seasonal Festivals: Engaging in seasonal festivals, whether for fall foliage or winter celebrations, embodies the festive spirit rooted in this destination’s cultural customs.

Frequently Asked Questions about Middlebury Accommodations

1. What are the top Accommodations in Middlebury?

There are a lot of options in Middlebury. If you plan on staying in the Middlebury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Middlebury:

2. How many Accommodations are available in Middlebury?

Currently, the total number of properties listed by RBO in 2026 is over 35 in the Middlebury area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Middlebury. 

3. What is the cancellation policy for accommodations in this area?

Cancellation policies vary depending on the property listing. You should review the specific terms listed for each accommodation or contact the host directly to understand their cancellation and refund policies.

4. Are there any special requirements or amenities I should know about before booking?

Many accommodations offer unique amenities; details are provided in each property listing. It’s best to read the description carefully or reach out to the host if you have specific needs or questions.

5. How do I ensure my reservation is confirmed for my travel dates?

Reservations are typically confirmed once you complete the booking process and receive a confirmation email. Be sure to check your inbox and contact the host if you have any concerns about your booking status.

6. What is the check-in and check-out process for accommodations in this region?

Check-in and check-out procedures vary by property. Details are usually included in your reservation confirmation, but you can also contact the host beforehand to clarify any specific instructions.

7. Is parking available at the accommodations near Middlebury?

Parking availability depends on the property you choose. Each listing provides details about parking facilities, so be sure to review this information or ask the host directly.