103+ Rental Villas and Private Getaways in Middlebury |
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Middlebury Vacation Rentals & One Degree Stays Homes

About Middlebury Vacation Rentals

There are more than 103 vacation rentals that are available in Middlebury. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Middlebury.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Middlebury, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Middlebury. Places to stay near Middlebury are 583.9 ft² on average, with prices averaging US $320 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Middlebury with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Middlebury

Type Count
Vacation Homes 42
Holiday Apartments 40
Cottages 4

Use these Quick Filters to Find a Vacation Rental in Middlebury

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Middlebury.

Weather in Middlebury, CT

View the weather forecast for Middlebury before booking your Middlebury Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Middlebury, CT

OneDegreeStays offers a large selection of top attractions around Middlebury. Research things to do on your vacation before you visit Middlebury.


Quassy Amusement Park
Middlebury Center Historic District
Lake Quassapaug
Yale University
Yale-New Haven Hospital
Toyota Presents Oakdale Theatre
Quinnipiac University
Shubert Theater
Palace Theatre
Lake Compounce
New Haven Green
University of New Haven
Choate Rosemary Hall
Warner Theater
CoCo Key Water Resort Hotel & Convention Center - Waterbury
New Haven City Hall
Southern Connecticut State University
Candlewood Lake
Elephant's Trunk Flea Market
Yale University Art Gallery

Other Places to Stay in Middlebury, CT


Middlebury Center Historic District 91 Properties
Lake Quassapaug 77 Properties
Quassy Amusement Park 67 Properties

Frequently Asked Questions About Middlebury?

What are the top vacation rentals 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 Vacation Rentals in Middlebury:

How many vacation rentals have private pools in Middlebury?

There are 2 vacation rentals with private pools near Middlebury. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Middlebury are best for families?

If you are looking for a family-friendly vacation home in Middlebury, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middlebury:

How many onedegreestays vacation rentals are available in Middlebury?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 103 in the Middlebury area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Middlebury. 


People Also Ask

There are 103 Middlebury, CT Vacation Rentals

Recently Booked Vacation Rentals in Middlebury