Middlebury, VT Cottage Rentals

Middlebury Cottage Rentals

Cottage

Charming Cottage within walking distance of Middlebury College/canoe available

2 Bedrooms 1 Bath 4 Guests

US $210/Night 7 Nights - US $1,470

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House

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

10.0

Exceptional

(30 Reviews)

2 Bedrooms 2 Baths 5 Guests

US $465/Night 7 Nights - US $3,254

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Bed & Breakfast

Swift House Inn

9.4

Exceptional

(48 Reviews)

8 Bedrooms 8 Baths 18 Guests 243.53 ft²

US $266/Night 7 Nights - US $1,860

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Highly Rated

Hotel

Swift House Inn

9.6

Exceptional

(339 Reviews)

1 Bath

US $285/Night 7 Nights - US $1,994

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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

US $760/Night 7 Nights - US $5,323

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Bed & Breakfast

Cornwall Orchards Bed & Breakfast

8.0

Excellent

(18 Reviews)

4 Bedrooms 4 Baths 8 Guests 180.3 ft²

US $175/Night 7 Nights - US $1,225

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Apartment

Yurt in Middlebury, Vermont

10.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 2 Guests 314 ft²

US $102/Night 7 Nights - US $711

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Hotel

Waybury Inn

8.8

Fabulous

(145 Reviews)

4 Baths 243.09 ft²

US $519/Night 7 Nights - US $3,633

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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

US $194/Night 7 Nights - US $1,355

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Hotel

Middlebury Sweets Motel

8.5

Fabulous

(125 Reviews)

2 Baths 220.66 ft²

US $172/Night 7 Nights - US $1,206

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Apartment

*Downtown Middlebury Waterfall Studio Apartment*

9.8

Exceptional

(8 Reviews)

1 Bedroom 1 Bath 2 Guests

US $357/Night 7 Nights - US $2,497

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Hotel

Middlebury Inn

8.4

Excellent

(484 Reviews)

23 Baths 394.52 ft²

US $173/Night 7 Nights - US $1,212

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More Top-Rated Cottage Rentals in Middlebury Area

Why Choose Rent By Owner for your Middlebury Cottage Rentals?

What makes our Cottage Rentals 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 Cottage Rentals stay?

Choosing the ideal time to visit here ensures you can enjoy the region's natural beauty and tranquility when the weather is most favorable, making your stay in this destination truly memorable.

Peak Season Highlights

Summer (June to August)

During the warmest months, this destination becomes lively with outdoor activities and scenic beauty, making it an ideal time for your stay in cottages.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Fall (September to October)

Experience the region's stunning fall foliage, attracting visitors seeking picturesque landscapes and vibrant colors-perfect for enjoying the serene environment of cottages.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

Winter (December to February)

The quiet winter months offer a peaceful retreat, with snowy views setting a cozy scene for your cottage stay here.

Average Temperature Daytime: 20°F to 35°F - Nighttime: 10°F to 20°F

Spring (March to May)

As nature awakens, you can enjoy fewer crowds and a tranquil atmosphere, ideal for a relaxing getaway in this scenic region.

Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Middlebury

How to Book Your Middlebury Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. 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 Cottage Rentals in Middlebury Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage Rentals 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 a spacious outdoor patio or deck for relaxing and entertaining amidst scenic views.
Take advantage of private gardens or landscaped yards perfect for outdoor gatherings.
Make the most of picnic areas equipped with tables and grills to dine alfresco during your stay.
Benefit from access to outdoor fire pits ideal for cozy evenings under the stars.
Utilize well-maintained walking trails or paths that weave through the surrounding natural beauty.
Relax by a private pond or water feature, common in many properties here, to enhance your outdoor experience.
Use designated parking areas that keep your vehicle conveniently close to your cottage’s outdoor amenities.

Top Attractions Around Middlebury

What attractions are nearby?

In this charming part of Vermont, you can explore a variety of outdoor activities such as hiking, cycling, and fishing in the scenic countryside, or enjoy local cultural experiences and quaint shops just a short drive away from your cozy cottages.

Family Activities

Middlebury College Museum of Art Engage with captivating artworks and exhibitions that inspire creativity for visitors of all ages in the heart of the region.
Snowbowl Recreation Area Enjoy outdoor adventures such as hiking, mountain biking, or picnicking amidst scenic natural beauty perfect for family outings.
The Vermont Maple Experience Discover the fascinating process of maple sugaring through interactive tours that are both educational and fun for kids and adults alike.
Otter Creek Falls Explore this picturesque waterfall with easy trails suitable for families seeking a relaxing nature stroll and stunning views.

Adult Activities

Visit the Middlebury College Museum of Art: Immerse yourself in a diverse collection of artworks and exhibitions at this cultural hub, enriching your stay in the area.
Explore the Otter Creek Falls: Enjoy a scenic walk along the creek and marvel at the natural beauty of the waterfalls nestled within the region's outdoor landscapes.
Tour local vineyards and wineries: Discover Vermont’s wine scene with guided tastings and tours that highlight the area's unique agricultural heritage.
Indulge in outdoor recreation at the Robert Frost Trail: Experience hiking or trail running on this popular route, offering stunning views and a peaceful environment for outdoor enthusiasts.

Other Places to Stay in Middlebury, VT

Middlebury - Warren

Explore 425 Properties

Addison County

Explore 132 Properties

Halpin Covered Bridge

Explore 56 Properties

Cornwall

Explore 51 Properties

Middlebury College

Explore 34 Properties

Kevin P. Mahaney '84 Center for the Arts

Explore 34 Properties

Porter Medical Center

Explore 33 Properties

UVM Health Network - Porter Medical Center

Explore 33 Properties

Porter Hospital

Explore 33 Properties

Holy Cow Inc.

Explore 32 Properties

National Museum of the Morgan Horse

Explore 32 Properties

Town Hall Theater

Explore 32 Properties

More Places to Stay Near Middlebury

Middlebury Travel Tips

How Can You Make the Most of Your Stay?

Explore Local Markets Visiting nearby markets allows you to enjoy fresh regional produce and handcrafted goods, enriching your stay in this charming destination.
Plan Outdoor Activities Take advantage of the area's natural beauty by engaging in outdoor pursuits such as hiking or cycling, which can be conveniently accessed from your cottages.
Sample Regional Cuisine Make time to indulge in the local flavors at nearby eateries to fully immerse yourself in the culinary culture of this region.
Visit Cultural Events Check out seasonal festivals and community events happening during your visit, offering authentic experiences close to your rental cottages.

Transportation Options

Middlebury Transportation Services This local transportation option offers reliable shuttle and bus services within the area, making it easy to explore without a car.
Rental Cars Several rental agencies operate nearby, giving you the flexibility to visit surrounding attractions at your own pace.
Taxi and Rideshare Taxis and rideshare options like Uber and Lyft are readily available for convenient door-to-door service around this charming destination.
Biking and Pedestrian Pathways The region features scenic bike routes and pedestrian-friendly streets, perfect for exploring the area's natural beauty and local sites on foot or bicycle.

Local Customs Options

Downhill Skiing Etiquette: Visitors often participate in skiing and snowboarding with respect for others’ space and adherence to trail rules, especially at popular winter resorts in the region.
Local Farming Traditions: The area values its agricultural roots through seasonal farmers markets and farm tours, emphasizing sustainable and community-focused practices.
Celebration of Art and Craftsmanship: Art festivals and craft fairs showcase the region’s artistic heritage, encouraging visitors to support local artisans and craftsmen during their stay.
Respect for Outdoor Preservation: Nature conservation practices are prominent, with hikers and outdoor enthusiasts encouraged to leave no trace while exploring the scenic trails around this destination.

Middlebury Cottage Rentals Frequently Asked Questions

1. What are the top Cottages 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 Cottages in Middlebury:

2. How many Cottages are available in Middlebury?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Middlebury area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Middlebury. 

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

Cancellation policies vary by listing, so it's important to review the specific property's terms before booking. Some cottages offer flexible options, while others may have stricter rules. For detailed information, consult the individual listing or contact the owner directly.

4. Are there any additional fees associated with booking a cottage here?

Additional fees such as cleaning, service charges, or security deposits are common and will be outlined in each listing. Be sure to read the full description and fee breakdown to understand all costs involved before confirming your reservation.

5. How do I find available dates for cottages in this region?

Availability calendars are typically provided on each listing. To determine when your preferred dates are open, simply check the calendar or reach out to the property owner for confirmation and further assistance.

6. Is there a minimum stay requirement when booking cottages here?

Minimum stay policies vary depending on the property and season. Some cottages may require longer stays during peak times, so always review the listing details or contact the owner to clarify any minimum night requirements.

7. What amenities can I expect in cottages in this destination?

Amenities differ across listings but often include essentials like Wi-Fi, kitchen facilities, heating, and outdoor space. For specific features, refer to the property description or message the owner to ensure the cottage meets your needs.