Photo by Ann Sair

Find Romantic Hotels in Middlebury, IN

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Middlebury Romantic Hotels

Top Middlebury Romantic Hotels

The Wellington Cottage
Family Cottage, 3 Bedrooms, Non Smoking, Lake View | Lake view

The Wellington Cottage

3.0 star property
10.0 out of 10, Exceptional, (3)
"It had everything we needed was off the beaten path, we swam in the water and used the paddle boat, nice and relaxing"
The Wellington Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for romantic hotels in Middlebury?
Are you and your partner looking for a romantic getaway? Our guests also enjoy Middlebury for its restaurants. If you want to explore the area, you might head to Stone Lake, Meadow Valley Golf Club, or Deutsch Kase Haus. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Middlebury?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Middlebury: The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Middlebury is 45 inches.
What is there to do in Middlebury?
There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Middlebury has to offer. If you and your partner are interested in sampling the area's cuisine, you'll enjoy Middlebury for its restaurants. A visit to Stone Lake, Meadow Valley Golf Club, or Deutsch Kase Haus might be just the ticket when you're checking out the sights.
What's the best way to get to Middlebury and around town during my romantic getaway?
This information about transportation options in Middlebury might help your romantic getaway go off without a hitch: To get to Middlebury, book a flight to Goshen, IN (GSH-Goshen Municipal), which is the closest major airport, located 11.5 mi (18.5 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.