Middlebury vacation rentals

Why visit Middlebury

1. Outdoor Adventures: Middlebury is perfect for hiking, picnicking, and exploring beautiful parks and lakes.
2. Charming Atmosphere: Enjoy a welcoming community filled with friendly locals and a rich history.
3. Local Shopping and Cafés: Discover delightful shops and quaint cafés in the historic neighbourhoods.
4. Diverse Accommodation Options: Choose from cozy vacation homes, stylish apartments, or charming cottages for your stay.
5. New England Charm: Experience the unique blend of relaxation and excitement that Middlebury has to offer.

Popular types of accommodation in Middlebury

Discover the charm of Middlebury with our diverse selection of vacation rentals. Whether you prefer a cozy private vacation home, a stylish apartment, or a quaint cottage, we have the perfect option for you. Explore our array of Middlebury vacation rentals, ideal for families or solo travellers. For extended stays, consider our monthly rentals to truly immerse yourself in this beautiful community. Your unforgettable Middlebury getaway awaits!

• Houses: This is the top choice among visitors to Middlebury, offering spacious and comfortable accommodations ideal for families or groups.
• Apartments: A close second, apartments provide a convenient and home-like atmosphere for those seeking a more urban vibe.
• Cottages: These quaint and charming options are perfect for a peaceful getaway, blending comfort with nature.
• Condos: Offering modern amenities, condos are a popular option for those wanting a blend of luxury and convenience.
• Cabins: For those who crave a rustic experience, cabins provide a cozy retreat amidst the natural beauty of Middlebury.**

Top attractions in Middlebury

Middlebury, Connecticut, offers a delightful vacation for outdoor enthusiasts and families alike. Explore the beautiful national and urban parks, as well as nearby lakes, which provide a perfect backdrop for adventure and cultural experiences. Whether you're hiking, picnicking, or simply soaking in the scenery, Middlebury invites you to uncover its local charm and outdoor activities, making it an ideal destination for a memorable getaway.

1. Quassy Amusement Park: A delightful family-friendly destination featuring thrilling rides, water attractions, and games. Its outdoor vibe ensures a fun-filled day for visitors of all ages, making it perfect for creating lasting memories.
2. Quinnipiac University: A historic institution renowned for its beautiful campus and vibrant culture. Explore its art galleries and attend engaging events that reflect the university's commitment to education and community.
3. Lake Quassapaug: A picturesque lake offering stunning scenery, romantic spots, and beach access. Ideal for relaxing, picnicking, or enjoying outdoor activities, it’s a serene escape just a short distance away.

Things to do recommended for couples

For a romantic getaway in Middlebury, consider skiing at Mount Southington Ski Area, enjoying thrilling water sports at Waterski Connecticut, or sipping fine wines at Haight-Brown Vineyard. Each experience offers a unique blend of adventure and intimacy, perfect for couples seeking memorable moments together.

Things to do recommended for families

In Middlebury, families can unwind at Kettletown State Park, enjoy thrilling games at Crystal Bees, and catch exciting matches at the Connecticut Tennis Center. Each location offers unique experiences, perfect for creating memorable moments together. Your family will love exploring these fun-filled spots!

Things to do recommended for groups

Groups visiting Middlebury can enjoy a show at the Palace Theatre, shop at Pilgrim Mall Shopping Center, and explore the eclectic finds at Elephant's Trunk Flea Market. These activities offer a perfect blend of culture, entertainment, and local charm for a memorable experience.

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

When planning your travel, whether it’s with a group, family, pets, or for extended stays, be sure to prioritize your preferences in the filtering process. Here are some helpful Vrbo booking tips for you.

• Traveling to Middlebury with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily refine your search for these options and more on Vrbo.
• Traveling to Middlebury with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a wise choice.
• Taking your pets with you to Middlebury: For many, a family vacation wouldn’t feel complete without their furry companions by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Middlebury: If you're seeking vacation rentals with special offers for stays of a month or longer, 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Middlebury

Middlebury, Connecticut, is a charming destination perfect for outdoor and family adventures. Explore the picturesque town, which boasts a welcoming atmosphere filled with friendly locals and rich history. Venture into nearby areas, such as historic Middlebury and its popular neighbourhoods, to uncover delightful shops and cafes. With its blend of relaxation and excitement, Middlebury offers an unforgettable experience for every traveller seeking a taste of New England charm.

• Waterbury: Located a mere 8.0km from Middlebury, Waterbury offers a vibrant blend of family-friendly outdoor adventures and entertainment. Known for its accessible casinos and educational venues, visitors can easily explore the area’s attractions like theme parks and waterparks, making it a great spot for all ages. Don’t miss the local event conference venues that frequently host exciting activities, providing an engaging travel experience for both families and adventure seekers.
• Shelton: Situated 18.0km from Middlebury, Shelton is a charming city that combines outdoor activities with urban amenities. With its historic and modern college universities, the city caters to visitors seeking both educational experiences and leisure. Enjoy the local resorts and casinos that offer a variety of entertainment options. Shelton’s event conference venues also serve as a hub for community gatherings, making it an inviting place to explore and connect with local culture.
• Southbury: Just 9.7km from Middlebury, Southbury is perfect for those looking to enjoy the great outdoors and spend quality time with family. This picturesque city is home to scenic lakes and amusement parks, providing plenty of opportunities for romance and relaxation. With options like casinos and resorts, Southbury ensures a well-rounded travel experience. Don’t miss the local event conference venues and theme parks, which add to the city’s charm and appeal.

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 April to May and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	28.0°F (-2.2°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	29.7°F (-1.3°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	47.8°F (8.8°C)	Light Rain	Mostly Sunny	Moderately High	Average
May	58.5°F (14.7°C)	Light Rain	Mostly Sunny	Moderately High	Average
June	66.6°F (19.2°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	73.2°F (22.9°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	71.6°F (22.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	64.6°F (18.1°C)	Light Rain	Mostly Sunny	Average	Average
October	54.0°F (12.2°C)	Light Rain	Mostly Sunny	Moderately Low	Average
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	34.3°F (1.3°C)	Light Rain	Mostly Sunny	Moderately Low	Average

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, booking an extended stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's groundbreaking Trip Board offers you a dedicated space to plan new journeys, pick up from where you last left off, and effortlessly manage your travel arrangements. You can easily access properties you’ve saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.