Find Romantic Hotels in Middlebury, IN

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Our top choices for Middlebury romantic hotels

Oakwood Resort

Oakwood Resort
3.0 star property
Syracuse
9.2 out of 10, Wonderful, (411 reviews)
"Wonderful breakfast."
United States
Sue
Oakwood Resort

Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife

Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife
Vandalia
10.0 out of 10, Exceptional, (74 reviews)
"Very nice, and very clean, we enjoyed our stay "
United States
Steve
The price is AED 529
AED 877 total
includes taxes & fees
24 Feb - 25 Feb
Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife

Amish Inn

Amish Inn
2.0 star property
Nappanee
8.6 out of 10, Excellent, (413 reviews)
"Excellent stay for the weekend"
United States
Meghan
The price is AED 294
AED 330 total
includes taxes & fees
22 Feb - 23 Feb
Amish Inn

Brook Pointe Inn

Brook Pointe Inn
2.0 star property
Syracuse
8.4 out of 10, Very Good, (404 reviews)
"Hot tub was nice to have in the room, it was so relaxing "
United States
Elizabeth
Brook Pointe Inn

Inn Between the Lakes

Inn Between the Lakes
2.0 star property
Three Rivers
10.0 out of 10, Exceptional, (5 reviews)
"It was a lovely stay and we got a warm welcome when we got there. The room was clean, modern and had everything one can need - including a kitchenette. Will stay there again"
United States
Peteris
The price is AED 587
AED 915 total
includes taxes & fees
1 Mar - 2 Mar
Inn Between the Lakes

Riverhaven! Gorgeous A-Frame On St Joe River!!

Riverhaven! Gorgeous A-Frame On St Joe River!!
Bristol
9.8 out of 10, Exceptional, (25 reviews)
"Convenient, pet friendly, responsive host, great location on the river"
United States
Nicole S.
The price is AED 883
AED 1,903 total
includes taxes & fees
22 Feb - 23 Feb
Riverhaven! Gorgeous A-Frame On St Joe River!!

Super 8 by Wyndham Goshen

Super 8 by Wyndham Goshen
2.0 star property
Goshen
7.4 out of 10, Good, (179 reviews)
"Great place to stay "
United States
Benito
The price is AED 264
AED 296 total
includes taxes & fees
27 Feb - 28 Feb
Super 8 by Wyndham Goshen

Beautiful Waterfront Home on Baugo Bay

Beautiful Waterfront Home on Baugo Bay
Osceola
9.4 out of 10, Exceptional, (38 reviews)
"Great stay and great host!"
United States
jennifer
The price is AED 2,204
AED 2,898 total
includes taxes & fees
28 Feb - 1 Mar
Beautiful Waterfront Home on Baugo Bay
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.

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Top Middlebury Hotel Reviews

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 Meadow Valley Golf Club, Stone Lake, 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 Meadow Valley Golf Club, Stone Lake, 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.