Holiday rentals in Middlebury

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middlebury

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Goshen

4.98 out of 5 average rating, 493 reviews

The Villa Goshen (Exclusive Use/All Guest Spaces)

An unforgettable stay awaits! Spectacular waterfront views from the home and guest deck, with outstanding amenities and accommodations, this is The Villa Goshen. Booking allows exclusive use of all guest bedrooms, common spaces on the main & upper floors, and the wooden guest deck area off the kitchen. No parties unless pre-approved. Hosts live on site in a separate basement apartment. Easy access to Notre Dame (45 min), Middlebury (20 min), Nappanee (20 min), and 25 to Shipshewana (25 min).

Guest favourite

Home in Three Rivers

5 out of 5 average rating, 15 reviews

Peninsula Paradise

Make some memories at this unique family-friendly home! Beautiful setting to accomodate a large gathering of friends and family. Water on three sides, two docks, lots of fish to catch, and kayaking. Enjoy the firepit on the water and watch the sun rise and set. Within 30 minutes of Kalamazoo and 10 minutes to Three Rivers for all the conveniences and entertainment options. Less than an hour from Notre Dame. A truly peaceful setting designed to help you relax and enjoy quality time!

Guest favourite

Guest house in North Webster

4.9 out of 5 average rating, 165 reviews

Come relax near beautiful Lake Webster

Our place is close to Webster Lake beach & boat ramps w/boat rentals. Whether you are looking for a relaxing getaway or to gather with friends & family you’ll love our place because of the location. We are centrally located between South Bend (Notre Dame) and Fort Wayne (Tincaps stadium/ Coliseum), close to many small towns w/ lakes, great eateries, & antique shops. With so much to offer you can find something for everyone or sit back & relax in our relaxed environment.

Superhost

Home in Elkhart

4.88 out of 5 average rating, 111 reviews

Lakeshore Cottage🎣 🚣‍♂️Waterfront/Great Wi-fi

Book your family getaway at this charming Lakefront home on Heaton lake! Enjoy swimming, fishing and a 4 person paddle boat. 3 minutes from Ideal Beach Family Water Park. Peaceful setting with a large back yard for games. Only 7 minutes from great food and shopping in Elkhart. Close to the toll road and 30 Minutes from Notre Dame Stadium. Excellent Xfinity wifi and TV. This is a very quiet neighborhood. No parties and there is a zero noise policy after 9 PM.

Superhost

Home in Three Rivers

5 out of 5 average rating, 7 reviews

Beautiful Family Friendly Beachfront Retreat

This three-bedroom, two-bathroom home sleeps up to 10 people and features a beautiful beachfront with a dock, hammock, and campfire area. Enjoy stunning sunsets from the deck, and dine in the screened-in porch or cook on the gas grill. The fully renovated interior includes all new appliances, a washer/dryer, TV, and Wi-Fi. Just a short drive to town for grocery stores and dining, this tranquil retreat is ideal for escaping the hustle and bustle of city life.

Guest favourite

Cottage in Wolcottville

4.91 out of 5 average rating, 65 reviews

Lakefront Getaway on Atwood Lake

Relax with the family at this peaceful Atwood Lake home. Close to Shipshewana, Indiana, heart of Amish Country. Visit the many parks in Lagrange County. After a small road trip, resign back at Atwood Lake to this beautiful shallow, white sandy beach. Enjoy kayaking, fishing, campfire and yard games with your family. Ready to use with full kitchen. We updated the patio furniture this year, it’s now blue! Start making your family memories now.

Guest favourite

Cottage in Sturgis

4.93 out of 5 average rating, 101 reviews

Charming Cottage on Beautiful Fish Lake

Newly renovated charming cottage on Fish Lake. Located in the heart of Amish county, featuring 2 bedrooms plus an enclosed porch which makes a great dining area or the perfect place to read a book or play games. Beautiful lake view and large deck for enjoying sunsets and sunrises. Fish Lake is an all sports lake with great fishing and shallow sandy bottom out more than 30 feet from shore. Enjoy a relaxing getaway at this peaceful lake.

Guest favourite

Cottage in Three Rivers

4.97 out of 5 average rating, 88 reviews

A hideaway retreat on a private lake for relaxing.

An extremely comfortable retreat experience for recharging yourself with water, sun, nature and quiet. This new cottage is on seven secluded acres, ideal for remote working and small reunions. The spring fed lake is wonderful for swimming, kayaking , fishing, pontooning or simply relaxing on the large decks. Kayaks, row boat, paddle boards, and pontoon INCLUDED. Ideal for introducing children to tent camping, wildlife and fishing.

Guest favourite

Home in Syracuse

5 out of 5 average rating, 17 reviews

Adorable Wawasee Cottage in Oakwood Park

History and memories ready to be made, get ready for beautiful sunsets at Lake Wawasee in Oakwood Park. A perfect location for dining out and grilling at home, The Oakwood Resort, The Frog Tavern, Louie's Bar and Grill, The Channel Marker, and more are within walking distance of this waterfront cottage. Park your boat on a 25-foot dock in a protected channel, or kayak out to Conklin Bay for the best birdwatching and fishing on the lake.

Guest favourite

Cabin in Three Rivers

4.96 out of 5 average rating, 23 reviews

Lake Front Getaway With a Hot Tub

Welcome to Long Lake, a 211-acre all-sports lake. This 850sf cottage features an open floor layout for the kitchen/dining/living areas. With large windows looking out onto the lake. On the front deck there is a large hot tub overlooking the lake, great for a quiet mornings or nights. There are three bedrooms one with a queen bed, a second with a double bed, and the third has two bunks (4 beds) There are 24 steps up to the entrance

Guest favourite

Home in Shipshewana

4.97 out of 5 average rating, 213 reviews

Ole Tin Rooster Sleeps 12+, Downtown NEW 4 Groups!

NEW! This curated Shipshewana staycation that awaits you! Fabulous farmhouse style including the largest live edge dining room table you’ve ever seen! You’ll be able to see many wonderful curated goods from our little town right here in a industrial farmhouse setting. Pack your bags, bring your family, gather your girlfriends and stay in the newest accommodations located right next to the famous Davis Mercantile.

Guest favourite

Home in Syracuse

4.94 out of 5 average rating, 88 reviews

Mt. Pleasant: Newly renovated with a hilltop view

Welcome to our cozy, modern home tucked away in a 100 year old neighborhood of friendly cottages on the edge of beautiful Dewart Lake. Our lake is touted for its cleanliness & excellent fishing. Discover a beautiful overlook of the water out the west facing french doors. This little cottage is a peaceful respite for our family, full of memories, & we hope it can be that for your family as well.