Best Vacation Homes in Middlebury
House
10.0(100 Reviews)
2 Bedrooms
2 Baths
8 Guests
1150 ft²
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $273/Night
7 Nights - US $1,911
House
9.3(14 Reviews)
3 Bedrooms
1 Bath
7 Guests
1302.43 ft²
- Parking
Child Friendly
Wellness Facilities
Security/Safety
US $234/Night
7 Nights - US $1,638
Cottage
10.0(9 Reviews)
1 Bedroom
1 Bath
- Parking
Ocean View- Balcony/Terrace
View
US $213/Night
7 Nights - US $1,490
Cottage
10.0(53 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $166/Night
7 Nights - US $1,161
House
9.1(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
635.07 ft²
- Parking
- Balcony/Terrace
Air Conditioner
Internet
US $171/Night
7 Nights - US $1,194
New
Apartment
10.0(30 Reviews)
1 Bedroom
1 Bath
6 Guests
750 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $112/Night
7 Nights - US $786
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
768 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,330
Bed & Breakfast
9.8(19 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Child Friendly
US $155/Night
7 Nights - US $1,086
Middlebury Luxury Rentals
House
10.0(34 Reviews)
4 Bedrooms
3 Baths
14 Guests
4000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $595/Night
7 Nights - US $4,164
Cabin
10.0(36 Reviews)
3 Bedrooms
3 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $550/Night
7 Nights - US $3,850
House
1 Bedroom
1 Bath
- Internet
- Child Friendly
Barbecue/Outdoor Cooking
Sports/Activities
US $527/Night
7 Nights - US $3,687
House
1 Bedroom
1 Bath
- Internet
- Child Friendly
- Barbecue/Outdoor Cooking
- Sports/Activities
US $507/Night
7 Nights - US $3,552
Cottage
10.0(19 Reviews)
4 Bedrooms
2 Baths
8 Guests
2207 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $459/Night
7 Nights - US $3,212
Cottage
8.6(11 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $405/Night
7 Nights - US $2,838
House
3 Bedrooms
3 Baths
8 Guests
1765.28 ft²
- Parking
- Balcony/Terrace
- Internet
- Child Friendly
US $404/Night
7 Nights - US $2,828
House
10.0(29 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $401/Night
7 Nights - US $2,810
Middlebury Pet Friendly Vacation Rentals
Boat Rental
8.8(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $202/Night
7 Nights - US $1,411
Hotel
7.6(286 Reviews)
1 Bath
301.39 ft²
Breakfast- Parking
- Balcony/Terrace
- Air Conditioner
US $145/Night
7 Nights - US $1,018
House
9.8(43 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $206/Night
7 Nights - US $1,441
Middlebury Large Vacation Homes
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
11 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $385/Night
7 Nights - US $2,697
House
9.8(44 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $303/Night
7 Nights - US $2,120
Cabin
10.0(1 Review)
2 Bedrooms
2 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $439/Night
7 Nights - US $3,073
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $250/Night
7 Nights - US $1,747
House
9.4(12 Reviews)
4 Bedrooms
2 Baths
13 Guests
2533 ft²
- Parking
- Kitchen
- Air Conditioner
- Child Friendly
US $278/Night
7 Nights - US $1,943
Apartment
5.0(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
1600 ft²
- Kitchen
- Air Conditioner
- Child Friendly
Laundry
US $145/Night
7 Nights - US $1,015
Other
10.0(33 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Kitchen
- Child Friendly
- Laundry
Bedding/Linens
US $250/Night
7 Nights - US $1,750
Why Choose Rent By Owner for your Middlebury Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Middlebury
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit this destination can enhance your experience, as different seasons in the region offer unique opportunities for enjoying your stay and making the most of your vacation rental experience.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination experiences its peak tourist season, making it ideal for those looking to enjoy outdoor activities and festivals.
Average Temperature Daytime: 85°F - Nighttime: 65°F
Fall (September to November)
The vibrant fall foliage attracts many visitors seeking a scenic escape and festive events, creating a lively atmosphere in this region.
Average Temperature Daytime: 70°F - Nighttime: 50°F
Off-Season Highlights
Winter (December to February)
With colder temperatures and fewer tourists, winter offers a quieter experience perfect for relaxing and enjoying the serene landscape.
Average Temperature Daytime: 40°F - Nighttime: 25°F
Spring (March to May)
As the area awakens from winter, early spring provides a peaceful setting before the busy summer crowds arrive.
Average Temperature Daytime: 60°F - Nighttime: 40°F
Weekly Weather Forecast for Middlebury
How to Book Your Middlebury Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middlebury
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for picnics and gatherings amid the natural scenery.
- Take advantage of spacious yard spaces ideal for outdoor games and activities with family or friends.
- Relax on private patios or decks that offer scenic views of the surrounding countryside.
- Make use of barbecue grills available for outdoor cooking and flavorful meals.
- Access well-maintained gardens or landscaped areas to enjoy peaceful walks or nature observation.
- Benefit from outdoor seating options designed for watching sunsets or unwinding after a day of exploring.
- Utilize nearby outdoor recreational facilities such as hiking trails or parks for active adventures.
Top Attractions Around Middlebury
What attractions are nearby?
During your stay, you'll find a variety of outdoor activities and local attractions nearby, offering a perfect blend of relaxation and exploration in this charming region.
Family Activities
- Elkhart County Fairgrounds: Experience family-friendly events and seasonal festivals that showcase the local culture and community spirit in the area.
- Kids Connection Playground: Enjoy a fun-filled day at this popular playground, perfect for letting children burn off some energy in a safe environment.
- Rural Heritage Center: Discover local history through interactive exhibits and guided tours that appeal to both kids and adults alike in this destination.
- Goshen Skate Park: Spend an active afternoon at the skate park, offering a great spot for skaters of all skill levels to practice and have fun with family members.
Adult Activities
- Exploring the Middlebury Historical Museum: Dive into local history and culture through engaging exhibits that showcase the area's rich heritage.
- Enjoying outdoor activities at Middlebury Community Park: Relax or get active in this popular park, offering walking trails, picnic areas, and recreational facilities for adults seeking leisure and exercise.
- Savoring regional flavors at local eateries: Indulge in authentic Indiana cuisine and craft beverages at nearby restaurants known for their welcoming atmosphere and regional specialties.
- Visiting specialty shops and galleries: Discover unique handcrafted goods and artwork, perfect for finding memorable souvenirs during your stay here.
Other Places to Stay in Middlebury, IN
Deutsch Kase Haus
Middlebury Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit During Local Events: Align your stay with regional festivals or events to experience the area's culture and community celebrations firsthand.
- Explore Nearby Dining Options: Taste authentic local cuisine by discovering popular eateries and hidden gems around this destination's vicinity.
- Utilize Central Location for Day Trips: Use your vacation rental as a convenient base to explore surrounding attractions and scenic spots in the area.
- Book Accommodation Close to Major Transportation: Select a property near key transit routes to maximize your sightseeing time and ease travel logistics.
Transportation Options
- Indiana Toll Road (Interstate 80/90): This major highway provides convenient access for road travelers exploring the region from Middlebury, Indiana.
- Plymouth Municipal Airport: A regional airport offering charter and private flight options, ideal for quick arrivals and departures here in the area.
- Greyhound Bus Service: Reliable bus routes connect to nearby cities, making ground transportation accessible for visitors staying in this destination.
- Local Taxi and Rideshare Services: Flexible transportation options such as taxis and rideshare apps are available to easily navigate around the region.
Local Customs Options
- Local Harvest Festivals: Participating in seasonal harvest festivals is a cherished tradition that reflects the region's rich agricultural heritage when you visit here.
- Farmhouse Hospitality: Expect warm welcomes and home-cooked meals that showcase the area's emphasis on farming customs and community bonding.
- Religious Celebrations: Traditional religious observances and parades are an integral part of the local culture, offering insight into the area's spiritual life.
- Historical Preservation Events: Engaging in events that celebrate the region's history allows you to connect more deeply with its past and cultural identity.
Middlebury Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Middlebury?
There are a lot of options in Middlebury. If you plan on staying in the Middlebury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middlebury:
- Charming, spacious home near towncenter amenities, resturants, trails and parks.
- | Hot Tub | Amish Farm Country | Pergola | Deck |
- HOT TUB | Beautiful Backyard Oasis|Newly Renovated
- Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
- Charming 1912 Bungalow in Middlebury Indiana
- Rustic Roots Cabin 3bd/3ba Cozy/Shipshewana/ND
- `Burning Pine Inn' Farm House in Amish country.
- The Back Porch Haven Stay in Amish Country yet close to Notre Dame
- Spacious, rural apt w/outdoor amenities - close to Shipshewana and Toll Road
- Beautiful Private Setting !
2. Which vacation homes in Middlebury are best for families?
If you are looking for a family-friendly vacation home in Middlebury, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middlebury:
3. How many Rentbyowner vacation rentals are available in Middlebury?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 60 in the Middlebury area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Middlebury.
4. What is the cancellation policy for vacation rentals in this area?
Each rental listing has its own cancellation policy. You should review the specific policy on the property’s page before booking, or contact the owner directly if you have any questions.
5. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or security deposits are typically listed in the property details. It's important to read these carefully during the booking process or ask the owner for clarification.
6. How do I ensure the vacation rental I choose is suitable for my needs?
You can find detailed descriptions, photos, and amenities listed on each property page. If you need further information, reach out to the owner to confirm that the property meets your requirements.
7. What steps should I take if I need to change or cancel my reservation?
Changes or cancellations depend on the individual property's policies. Review the cancellation terms on the listing and contact the owner promptly to discuss your request or to initiate a cancellation.
8. Is it safe to book through this platform in the region, and how is my personal information protected?
The platform employs secure booking processes and privacy protections to keep your personal information safe. For peace of mind, always verify the listing details and communicate through official channels provided on the site.
Middlebury Top Rated Vacation Rentals
US $133/Night
7 Nights - US $933
Hotel
9.3(737 Reviews)
4 Baths
441.32 ft²
Private Pool
Oceanfront- Hot Tub
- Parking
US $169/Night
7 Nights - US $1,183
US $145/Night
7 Nights - US $1,015
