Top 9 Airbnb Vacation Rentals In Middlebury, Vermont - Updated 2023


Spread over 39.2 square miles (101.5 square kilometers), Middlebury has been featured in several films. The prominent Middlebury College that brought in international students was briefly mentioned in The Simpsons and American Graffiti. The city’s impressive Middlebury Falls, an 18-feet (5.49-meter) urban waterfall along Otter Creek, was featured in Me, Myself, and Irene. Addison County’s seat has, indeed, captured the hearts of visitors and cinema viewers alike. This town has produced some of America’s prominent personalities, including the award-winning author Julia Alvarez, the inventor and manufacturer John Deere, and several other senators and athletes. Discover the beauty and wonder of this shire town by staying at one of the town’s many vacation rentals. Not sure where to start? We’ve rounded up a list of the top Airbnb vacation rentals in Middlebury, Vermont, that will allow you to enjoy everything this shire town has to offer.

1. Stylish cottage near Middlebury College (from USD 425)

Accommodating six people, the stylish white-walled cottage features a bath, lounge, free private parking and kitchenette that includes microwave, refrigerator, coffee maker. Guests can’t help but admire the beautiful French doors that open up to the balcony. Guests also love the convenience of the property’s location. Middlebury College and the village center are within walking distance from this three-bedroom Airbnb vacation rental. If you don’t want to skip appointments with the college, stay at this stylish cottage.

The Barn at Middlebury
Middlebury, Vermont, United States
157 reviews Superhost  Wifi Available
Entire rental unit 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
it was wonderful the flowers wine and cheese delicious breakfasts gorgeous linens
if you thought you knew what a savory or sweet breakfast bun tasted like you are wrong
cozy gas stoves comfortable furnishings amazingly comfortable beds with linens that rivaled any luxury hotel
don't turn down that breakfast invite :)after three wonderful nights it was tough to leave
all the beds were incredibly comfortable with soft sheets pillows and blankets
great beds and linens super clean and newly updated
the space is beautiful sparkling clean and so peaceful
so clean and with high end amenities
this place is not only spotlessly clean but also stylish and includes such thoughtful touches
the home is just as described- clean tidy beautifully decorated and amazing attention to details
the hosts were gracious & welcoming
they were wonderful kind hosts and their home is gorgeous
can’t thank our hosts enough or recommend more highly
they are generous and kind people who took great care of our family
they are incredibly gracious hosts
great location for a family gathering
the location is easy walking distance to town and the college
the location was an easy walk to dinner in town or a walk in the woods (tam)
it was like going to spend time with close relatives
walkable to everything and very enjoyable space
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2. Holiday rental in a scenic location (from USD 110)

Do you want to stay close to town but crave for a peaceful environment? Your best option is this one-bedroom accommodation that fits four guests comfortably. It has a fully equipped kitchen that allows long-term guests to cook and save on meals. The house is located along Otter Creek, a scenic location that’s perfect for night strolling or early morning jog. The ground level is a law office. What this means for you is a restful sleep at night.

In the Hollow
Middlebury, Vermont, United States
179 reviews  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
when not sleeping the living room was a nice spacious and comfortable gathering spot
there is a comfortable double bed and also a pull-out queen sofa bed
the apt is very comfortable and spacious with a lot of middlebury memorabilia
bed was comfortable kitchen well appointed with muffin coffee teas fruit
jane's place on mill's street was excellent the accommodation was comfortable and perfectly fit for a 1-2 person stay
it was clean and comfortable
it's clean and well appointed
the space was cozy clean and comfortable
also clean and comfortable with an easy check in
bed is super comfy and place was very clean
accommodating and friendly host
she was very welcoming and helpful throughout our visit
jane was a wonderful host
she is so welcoming and kind
jane is a great host
great downtown location easy access to stores and restaurants
the location of the apartment is ideal in the middle of middlebury
fabulous location in the heart of middlebury
froghollow is in an ideal beautiful location
beautiful place in a great location you can literally almost walk everywhere
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3. Private guest house near US Route 7 (from USD 159)

Stay in a private guest house and enjoy the freedom of living in a cozy space without having to share with strangers. Here, you’ll find a kitchenette for your quick brekky. This top Airbnb vacation rental fits three and is near US Route 7. You can visit Middlebury College briefly, then head on to other destinations - New Hampshire or Massachusetts perhaps?

Private Apartment in Middlebury
Middlebury, Vermont, United States
118 reviews  Wifi Available
Entire guest suite 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the space was spacious and comfortable with all the necessary amenities
the ac unit is in the living room not the bedroom but it was cool temperature-wise regardless
the kitchen amenities are great -- fridge microwave sink -- and the bedroom is cozy and very comfortable
the couch in the living room is really comfortable and it was stocked with books and games
appreciated the ceiling fans and a/c
very clean and comfortable place
apartment clean cozy and comfortable
it was super clean and the beds were comfortable
the apartment was neat and clean well stocked with hand soap paper towels and other cleaning supplies
very clean and comfortable place to stay
really accommodating & friendly host
miles was a good host checking in with us to make sure we had what we needed
miles was a great host gracious and considerate
miles was an excellent host for great recommendations
the bed and pullout were very comfortable and miles was very responsive to our questions
the location is terrific
the location is perfect - just a few miles or a 5 minute drive to everything
great place to stay conveniently located near town
super convenient to downtown middlebury but in a very quiet and peaceful location
great easy location for getting arouns
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4. Riverside house with easy access to ski resorts (from USD 76)

A good location can bring your Middlebury holiday to greater heights. Choose this fully equipped riverside house on East Middlebury for your next six-person trip. Predominantly and stylishly white, this air-conditioned Airbnb vacation rental provides a relaxing environment for guests. You can cook meals, wash clothes, lounge over coffee, work on projects, and conveniently visit ski resorts. This three-bedroom property is accessible from Middlebury College, too. Now you know where to stay during winter.

Beautiful Location - East Middlebury River House
Middlebury, Vermont, United States
224 reviews Superhost  Wifi Available
Entire rental unit 3 Beds 7 Guests 3 Bedrooms 1 Bathroom

Accommodates: 7

Top guest reviews
Amenities & Room:
cast iron skillet stainless pans etc) all of which were in great condition
the apartment is better than see in photos
the apartment was incredibly clean with very nice amenities and comfortable beds
abbott's place is fantastic loved the white decor comfortable bed and lavender bathroom products so warm and inviting
the bed was quite comfortable with nice linens throughout
very clean and great communication
very clean and stylish home
incredibly clean modern minimalist yet technologically advanced space
very clean and safe place
it is spotlessly clean
abbot is a wonderful host
abbott is a wonderful host
abbott was also helpful throughout and supplied us with great recommendations for the area
abbot was a perfect host — responsive helpful and gracious
abbott is a great host responds quickly to emails
charming apartment in great location
great place in a great location
abbott's place is in a fabulous location just a few minutes from middlebury
the location was perfect fir going anywhere especially downtown middlebury
delightful apartment in a great location
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5. Fully equipped house with an entertainment room (from USD 395)

Newly renovated, this large house features amenities to make your stay comfortable and fun. Stay cozy in air-conditioned spaces (yes, all floors have AC). Cook your favorite dishes in the gourmet kitchen. Enjoy nights of fun games and exciting movies in the family room. Discover Middlebury on foot as this top Airbnb vacation rental sits right in the middle of the town. Plus, it fits eight. Big families will do well staying at this homey holiday rental.

Walk Everywhere in Middlebury - 5 Beds and A/C
Middlebury, Vermont, United States
65 reviews Superhost  Wifi Available
Entire home 5 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the bedrooms were large and comfortable with multiple sleeping options and plenty of space
comfortable with spacious main space/kitchen and bedrooms
the kitchen and living room space is perfect for gathering together friends - and for just chilling out
space was ample clean and well decorated
super clean and very very convenient location
the house was so clean and spacious great for a large group
this was a clean comfortable lovely property with nice back porch and comfy beds
ashley’s place is convenient spacious and sparkling clean
ashley was very responsive and friendly
great location to explore the area
great stay in a convenient location
beautiful house in a great location we loved it
this is a beautiful home and a wonderful location
adventures of all sorts are just a walk or car ride away
Read more reviews

6. Four-bedroom house with Victorian charm (from USD 314)

The expansive indoor space of this Victorian-inspired, two-level house fits large groups of eight. Cozy beds, pastel-colored cushions, warm lights, and dainty decor here and there, this Airbnb vacation rental is nothing but charming. You’ll find cooking in the fully equipped kitchen surprisingly enjoyable. The property sits in the middle of Middlebury, where there are shops, restaurants, and art galleries. You can take a stroll for a munch or simply stay indoors for Netflix series.

Entire House in Middlebury - Walk Everywhere
Middlebury, Vermont, United States
121 reviews  Wifi Available
Entire home 4 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
air conditioner kept things cool
the house is modern comfortable and has all the amenities
the beds were very comfortable
the rooms are all upstairs with very comfortable beds and a bathroom
also good table to allow us all to have dinner play board games etc
very clean and very comfortable
clean and plenty of space
very clean comfortable and convenient
the place was spotless comfortable and full of charm
space was clean and well equipped
they were great hosts
host was very responsive and answered questions quickly
the hosts were responsive and very helpful
meghan was very responsive to our questions
outstanding hosts meghan and gregory are super quick to respond and provided local tips upon request
the location is excellent~ it is walking distance to all the main attractions
great house close to everything with really cute and cozy touches
a wonderful airbnb walking distance to everything
well appointed great location pristine
it's in a great location
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7. Studio within 5-minute walk to Middlebury College (from USD 124)

Conveniently located within walking distance to Middlebury College, this Airbnb vacation rental is ideal for guests attending college functions and appointments. You can shower for five minutes and be on campus in the next five minutes. The studio is set above a two-car garage, with its private deck, dining, kitchen, and bath. You can eat meals in the patio overlooking the campus grounds or take your pick from the many dine-in restaurants in the nearby area.

Cozy Studio Apt. Walk to College and Town!
Middlebury, Vermont, United States
45 reviews Superhost  Wifi Available
Entire loft 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
no ac but multiple fans and good ventilation
the treehouse is cozy—everything you need plus a private deck terrace overlooking a nice garden
the place was clean and overlooked a beautiful backyard
mike and barbara were wonderful thoughtful hosts the apartment space was lovely clean private and well-located
mike and barbara were great hosts
the owners are very kind and attentive
we highly recommend this airbnb and these wonderful hosts
michael is a fantastic host and made sure we had a comfortable and enjoyable stay
window curtains could be a little tricky to adjust but the hosts were super responsive welcoming and helpful
great location and very private
place is immaculate very easy check in and the location is super close
it was an excellent location good value and very pleasant place to stay
this place was awesome michael was super kind and courtesy
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8. Three-level townhouse with great balcony views

Delight yourself with gorgeous views of the Snake Mountain when you stay at this fully furnished townhouse. Boasting three levels, this Airbnb vacation rental features not just one but two balconies, one being hooded. It has sleeping provisions for six guests, plus cooking and washing facilities. Glass sliding doors break the boundary between the great outdoors and the indoor space. You’ll feel at one with nature, even while lounging in the living room or sleeping in your bedroom.

Middlebury Townhouse
Middlebury, Vermont, United States
94 reviews Superhost  Wifi Available
Entire townhouse 4 Beds 7 Guests 3 Bedrooms 1 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
there is no ac but it’s well ventilated & there are floor fans to keep you cool
the nights were very comfortable and quiet with beautiful views from the back porch
1st floor has the full bathroom n washer dryer and a nice big bedroom
we loved this place especially the beautiful views and the stylish rooms
comfortable nice view - a good stay when in middlebury
everything was very clean
ted’s place was very clean and very easy to find
the property was clean and as described
the unit was perfectly cleaned and exactly as described
the house was spacious and clean
ted was a great host
the host was very responsive and helpfull
ted is a great host and was very responsive when we had questions
ted was very responsive and all worked out smoothly
ted was a very communicative and kind host and the whole experience was seamless
comfortable place close to town
location minutes from middlebury college was ideal
and a great location close to but not in the middle of downtown
great location just outside of middlebury
awesome place in a great location
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9. Apartment with nice mountain views

What can be more relaxing than waking up to gorgeous mountain views? You can very well have your dreamy Middlebury stay in this two-person apartment located in a park-like neighborhood, complete with a private garden. Your kitchenette includes a fridge that your kind host fills with breakfast food like bread, milk, jam, and sometimes organic eggs. You’ll need a good breakfast, especially when you decide to try the Trail Around Middlebury, which boasts of multiple scenic trails for hiking and biking. The area is only five minutes away.

Park-like Neighborhood in Middlebury
Middlebury, Vermont, United States
30 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
there was fresh juice local milk granola bread and coffee stocked in the kitchen
the shower was very hot with excellent water pressure which we appreciated
during the stay our unit was well stocked with breakfast food juice tea and yummy lake champlain chocolates
the place was clean and inviting
very clean cute and cozy
theresa's place was very clean cozy and welcoming
the space is clean quiet and very convenient to town
the apartment is clean and thoughtfully appointed and theresa is very responsive and helpful
the host (theresa) was very responsive and helpful via text/airbnb messenging
the area is quiet with peaceful and beautiful walks nearby and a very friendly host
it is located in a beautiful country setting close to town
this is a wonderful location and a very comfortable apartment
the location is excellent being a stones throw from the center of middlebury
neighborhood was quiet and the park like setting was scenic and a nice place for a walk
wonderful location near middlebury college in a quiet neighborhood with very friendly neighbors and plenty of great walks
Read more reviews

Stay close to your destination in Middlebury

Location is key for having a comfortable stay in Middlebury. Choose whether to stay close to Middlebury College, scenic hiking trails, or ski resorts. Your choice of accommodation depends on your purpose of travel. When traveling during the busy college season or summer from June to August, it is wise to browse accommodations in advance. Start planning your trip with our list of top Airbnb vacation rentals in Middlebury, Vermont.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Jahz is a Philippine-based writer who enjoys solo travels as much as group adventures. She believes that life is too short to be spent living in one place, so she makes it a point to experience a...Read more

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