Owner Direct Vacation
Rentals in Middlebury
The Best Owner Direct Vacation Rentals in Middlebury. Explore thousands of vacation home rentals, large cabins, and villas near Middlebury
GUESTS
Explore the Best Middlebury Vacation Homes
Looking for the perfect place to stay in Middlebury? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Middlebury character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
Why Travelers Love Using
Owner Direct to
Find Middlebury Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Middlebury
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
Popular Neighborhoods for Middlebury Vacation Rentals
What are the best areas to stay in Middlebury
Discover the top neighborhoods in Middlebury and choose a place that suits your stay.
Monday Feb 2
Middlebury, Vermont
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Middlebury vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Middlebury
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
How to Reserve Your Middlebury Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Middlebury Vacation Rental FAQs
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:
- Middlebury Gem open concept and 5 minutes from town
- Custom Home just minutes from Middlebury
- Beautiful, well-appointed, 1-bedroom apt with gorgeous views
- Experience Vermont charm! Up to 5 bedrooms available Please inquire for rates
- Mountain-view House ~ Mins To Middlebury, Flex Cancellation Policy
- Large And Luxurious Farmhouse - Close To Town And College!
- Middlebury Home with Sunset views!
- Upscale 4BR Cottage Walk to Middlebury College & Town Hot Tub Pet-Friendly
- Downtown Middlebury River House
- Sun-filled, quiet country home on 27 acres with mountain views
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 vacation rentals are available in Middlebury?
Currently, the total number of properties listed in 2026 is over 45 in the Middlebury area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Middlebury.