Photo by Ann Sair

Search Resorts in Middlebury

    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 prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Resorts in Middlebury

Oakwood Resort
Exterior

Oakwood Resort

3.0 star property
9.2 out of 10, Wonderful, (362)
"Beautiful property, friendly staff, and clean rooms! "
Oakwood Resort
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

What is Middlebury like for a resort vacation?
You deserve a vacation, and a resort is the perfect place to pamper yourself with the amenities and services you need for a relaxing time in Middlebury. One of the comfortable resorts in the surrounding area could be just what you're looking for, whether you want an amazing pool, blissful spa treatments, or fun activities to try.
What's a favorite resort in Middlebury?
Here's our top-rated resort near Middlebury: Oakwood Resort - Beach resort. 18.5 mi (29.7 km) from Middlebury. Features 2 restaurants, 2 bars, and a fitness center.
What can I do in Middlebury?
Grab your golf clubs for a game at Meadow Valley Golf Club, or bring the kids to Deutsch Kase Haus for some family fun. For more to see in the area, you can spend time at Trout Lake or Stone Lake.
What's the weather like 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's the best way to get to and around Middlebury?
Fly into Goshen, IN (GSH-Goshen Municipal), which is located 11.5 mi (18.5 km) from the heart of the city. Otherwise, you can search for flights to South Bend Intl. Airport (SBN), which is 31.3 mi (50.4 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.