99+ Private Villas and Holiday Rentals in Middlebury |
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Middlebury Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Middlebury

Discover more than 99 vacation rentals available in Middlebury. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Middlebury.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middlebury, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Middlebury. On average, places to stay near Middlebury offer 571.99 ft², with nightly prices averaging US $321.

With Casai, finding and comparing holiday rentals in Middlebury is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Middlebury

Type Count
Vacation Homes 41
Holiday Apartments 37
Cottages 4

Use these Quick Filters to Find a Holiday Rental in Middlebury

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal 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

Casai 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 holiday rentals in Middlebury?

With numerous options available in Middlebury, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middlebury:

How many holiday rentals have private pools in Middlebury?

Discover a selection of holiday rentals with private pools near Middlebury with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Middlebury are best for families?

If you're searching for a family-friendly holiday home in Middlebury, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Middlebury:

How many Casai.nz holiday rentals are available in Middlebury?

As of 2025, Casai boasts over 99 properties listed in the Middlebury area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middlebury.


People Also Ask

There are 99 Middlebury, CT Holiday Rentals

Recently Booked Holiday Rentals in Middlebury