Holiday rentals in Middlebury

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Top-rated holiday rentals in Middlebury

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

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Guest favourite

Home in Goshen

4.98 out of 5 average rating, 504 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 Niles

4.97 out of 5 average rating, 173 reviews

Riverwalk Retreat on Main, fully updated Victorian

Beautiful 5 bedroom, 2 bath Victorian home in the heart of Niles, MI Recently remodeled with queen bedroom on main floor! 2 blocks from Riverwalk park All bedrooms and living room/game room have mounted flat screen smart tvs Private back yard with fire pit and corn hole, front and back porch 3-min. walking distance over the river to charming restaurants and shops on Main Street 10 miles from University of Notre Dame, and nearby wineries and breweries 30 min. to St. Joseph and New Buffalo, MI

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

Home in Warsaw

4.96 out of 5 average rating, 114 reviews

Relax 15 guests can enjoy Holidays & Everyday

Beautiful home in a quiet neighborhood on Barbee Chain of 7 Lakes ,Irish Lake Channel.Can be used for reunion corporate event birthday, bachelor bachelorette parties,fire pit Corn hole boards along with a fully stocked kitchen. Oklahoma Joe’s Gas &charcoal grill with a smoker box, 4 bedrooms 2 bath fenced in back yard for pets &kids.Pet fees apply. Parking for trailers trucks 2 Beautiful decks with gorgeous sunsets.Nice beach close by.Pontoons available to rent separately at the home.

Guest favourite

Cottage in Three Rivers

4.97 out of 5 average rating, 88 reviews

A hideaway retreat on a private lake for relaxing.

INQUIRE FOR WINTER RATES FOR WEEKEND GETAWAYS!!! 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 Bremen

4.95 out of 5 average rating, 146 reviews

"SERENITY COTTAGE" Picturesque lake front w/3 bdr!

"SERENITY COTTAGE" A private lake front home on the north shore of Lake of the Woods. 35 min. to Notre Dame and 19 min. to Amish country, Nappanee, IN. This charming three bedroom home in a quiet setting is the perfect place to catch some much needed R & R with family & friends. Park you boat at our private pier or just enjoy observing the wildlife, sunsets, etc. Observe the grace of great blue herons, mama ducks with their ducklings, and you may catch a glimpse of a bald eagle!

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, 113 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 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

Home in Shipshewana

4.97 out of 5 average rating, 216 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.

Superhost

Home in Vandalia

4.88 out of 5 average rating, 57 reviews

Beautiful Large Lake Home in Southwest MI

Our place is great for couples, families (with kids), and large non-rowdy groups, In addition to summer and fall rentals, the house can be rented for ND football weekends. It is a 40-minute drive to the stadium. If you want to be closer to ND (within a mile) check out our other listing here on AirBNB. NOTE: Fireworks are NOT to be used on our properties at anytime. Violation could result in immediate eviction.