TOP 30 Vacation house rentals in Middlebury, Vermont

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Pitkin Rental Cottage is a charming real estate agency located at 556 Weybridge Street in Middlebury, Vermont. We offer a selection of beautiful cottages available for short-term and long-term rentals. Our cozy, well-maintained properties are perfect for individuals, couples, and families looking for a peaceful retreat in the picturesque Vermont countryside. With our personalized service and attention to detail, we strive to make your stay with us a memorable and enjoyable experience. Contact us today to book your stay at Pitkin Rental Cottage and discover the beauty of Vermont living.

Champlain Valley Properties is a reputable real estate agency located at 70 Court Street in Middlebury, Vermont, United States. Our dedicated team of experienced agents is committed to helping clients buy, sell, and rent properties in the beautiful Champlain Valley region. With a focus on personalized service and attention to detail, we strive to make the real estate process as smooth and stress-free as possible for our clients. Contact us today to see how we can assist you with all of your real estate needs.

The Rooms at The Stone Mill is a charming lodging establishment located at 3 Mill Street in the picturesque town of Middlebury, Vermont. Nestled in a historic stone building, this cozy retreat offers a unique and inviting atmosphere for guests to relax and unwind. Each room is beautifully appointed with modern amenities and thoughtful touches, ensuring a comfortable stay for every visitor. The convenient location allows guests to easily explore the charming streets of Middlebury, as well as nearby attractions such as the Middlebury College campus and the scenic Vermont countryside. Whether you are visiting for business or pleasure, The Rooms at The Stone Mill provide a peaceful and welcoming sanctuary for your stay in Vermont.

Waterhouses: Lodging, Campground & Marina is a picturesque institution located at 937 West Shore Road in Salisbury, Vermont, United States. Offering a unique combination of amenities including a bar, campground, lodging, park, and store, Waterhouses is the perfect destination for those looking to enjoy the beauty of Lake Dunmore. Situated just South of Middlebury and North of Rutland, Waterhouses is nestled at the foot of Sunset Hill with stunning views of Mt. Moosalamoo. The 160-acre property features a variety of campsites ranging from grassy to wooded to riverfront, all equipped with water and electricity. Guests can choose from tent sites, pop-up sites, trailer sites, and even sites for Class A RVs and 5th wheels. For those looking for a more secluded experience, the Hideaway cabin on Sunset Hill offers a private retreat surrounded by nature.

On the Creek Bed and Breakfast is a charming lodging located at 284 Pulp Mill Bridge Road in Weybridge, Vermont, United States. This beautiful 1827 Federal home has been fully updated and is now a licensed bed and breakfast. Guests can enjoy a pleasant walk to Middlebury town and college from this historic property. The bed and breakfast offers a private suite in a separate wing of the house with its own entrance. The suite features two bedrooms with queen beds, comfortable mattresses, and sun-dried cotton sheets. Due to Covid-19 restrictions, breakfast is no longer served, but guests have access to a refrigerator, microwave, and electric kettle for light food preparation.

Pink House Farm is a charming institution located at 299 Ridge Road in Cornwall, Vermont, United States. Owned by Middlebury College graduates Janet Halstead Franklin ’72 and Churchill Franklin ’71, this picturesque farm offers a serene and peaceful retreat for visitors looking to escape the hustle and bustle of everyday life. The farm features beautifully designed interior spaces that are perfect for relaxation and unwinding. Whether you're looking to host a special event or simply enjoy a weekend getaway, Pink House Farm has everything you need to make your stay memorable.

Whittaker Real Estate Inc. is a long-standing family business located at 14 Mount Pleasant Drive in Brandon, Vermont, United States. Since 1958, we have been serving northern Rutland County and southern Addison County, helping clients with their real estate needs in areas such as Brandon, Pittsford, Middlebury, and more. As a general contractor and real estate agency, we have a deep knowledge of the local community and can provide valuable insights to those looking to buy or sell property in the area. Our team, consisting of Tom and Carolyn, is dedicated to providing expert guidance and personalized service to our clients.