Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

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Top guest favorite
Apartment in Middlebury
4.95 out of 5 average rating, 73 reviews

*Downtown Middlebury Waterfall Studio Apartment*

Downtown Middlebury furnished studio apartment with a picturesque view of Otter Creek waterfalls! This historic 1700s building has retail shops on the first floor and the apartment is upstairs. Conveniently walkable to restaurants, shops, and Middlebury College. Nearby favorites: Otter Creek Bakery, Two Brothers Tavern, Mad Taco, and Yogurt City. Please note: We use hotspots for internet; service during your stay is not guaranteed! No onsite parking provided but there is public parking nearby.

Top guest favorite
The exterior of the cottage displays a modern design with light gray siding and a vibrant purple door. A small porch offers space to relax, while surrounding trees enhance the peaceful environment. A pathway is visible, leading to the entrance of the home.
Home in Middlebury
4.98 out of 5 average rating, 207 reviews

Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage is located in the heart of Middlebury on a peaceful side street. Completely renovated, AC & heat everywhere, lots of comfy beds, great deck with grill and fire ring, fast WiFi, king bedroom for the parents, fun guest room with 1 queen, 1 full & 1 twin, full bath & 1/2 bath. Walk to restaurants, shops, grocery stores, and even the College! Incredibly well designed home can comfortably accommodate a couple or a crowd! Brand new 55" Smart TV, new beds, linens, sofas, etc.

Top guest favorite
A bright living area features tall windows allowing natural light to fill the space. A comfortable white sofa, accent chairs, and a wooden coffee table are positioned on warm wooden flooring. A bookshelf with numerous books adds character, while a desk provides a workspace.
Apartment in Middlebury
5 out of 5 average rating, 213 reviews

The Barn at Middlebury

The Barn at Middlebury is within a 10 min. walk of the village center and 15 min to Middlebury College. The renovated barn is attached to the owners' residence. The separate guest quarters have a private entrance and include 3 newly renovated bedrooms, with two baths. The 1st floor bedroom has a Livingroom, kitchenette (Nespresso, microwave, Ref/Freezer, dishwasher, sink). Washer/Dryer. The 2 other 2nd Fl bedrooms share a large private bath. A terrace and screened porch is available.

Top guest favorite
Cottage in New Haven
4.99 out of 5 average rating, 196 reviews

Hilltop Cottage With a View

Our newly built cozy and relaxing guest cottage is located in New Haven . It has stunning views and gorgeous sunsets!! Located just seven miles from Middlebury ,Vergennes and Bristol . All of which have great shops and restaurants! Close to many local attractions including ,Woodchuck Cider house, Lincoln Peak Vineyard, Ski areas, Hiking , rivers, lakes, restaurants and much more! Our goal was to provide guests with a home away from home! We feel our cottage offers that and much more.

Top guest favorite
A covered patio area features four green chairs arranged around a small step. Potted plants add a touch of color, while a spacious lawn extends in front of the home, framed by trees and a clear blue sky.
Home in Middlebury
5 out of 5 average rating, 106 reviews

The Little House

You will be close to everything the village of Middlebury has to offer when you stay at this centrally-located, light-filled home. A short walk to Middlebury's coffee shops, retail stores, and restaurants. Very close to Middlebury College and just minutes from hiking, biking, skiing, and many other outdoor activities in the mountains and on the shores of Lake Dunmore or Lake Champlain. Perfect for a quiet stay in town or as an adventure home base. Off-street parking for two cars.

Top guest favorite
A bright bedroom features a spacious bed adorned with white linens and subtle blue detailing. Natural light enters through two windows, accompanied by blinds. A potted plant adds a touch of greenery, while built-in shelving provides storage options.
Apartment in Middlebury
4.98 out of 5 average rating, 157 reviews

Mountain View Retreat

This clean, quiet, ground-level apartment enjoys an out-of-town feel and expansive mountain views while being conveniently located to the town of Middlebury, Middlebury College, the Green Mountain National Forest, the Middlebury College Snow Bowl and the Rikert Nordic Center, and more. This 1 bedroom/1 bath apartment features an open living concept and a fully equipped kitchen and is just 1.5 miles from restaurants and grocery stores and 2 miles from the college.

Top guest favorite
A charming wooden house is nestled among lush trees, with soft exterior lighting illuminating its entrance. A circular stone garden bed is featured prominently in the foreground, surrounded by a well-manicured lawn. A red vehicle is parked nearby along the road.
Apartment in Middlebury
4.93 out of 5 average rating, 68 reviews

Chipman Hill Apartment.

This elegant apartment in our home on Chipman Hill in Middlebury is a short walk to town and Middlebury College and steps away from the Chipman Hill forest, with its miles of hiking and biking trails and many scenic vistas. A private entrance leads to a screened porch, living room, kitchen, and bathroom on the second floor. Skylights in the large third-floor bedroom offer breathtaking views of the Champlain Valley and the Adirondack Mountains.

Top guest favorite
A historic two-story home with blue siding is showcased, featuring white trim and black shutters on its windows. A welcoming front porch is visible, surrounded by well-manicured lawns and garden plants, creating a serene outdoor atmosphere.
Home in Middlebury
4.96 out of 5 average rating, 105 reviews

Walk Everywhere and Enjoy a Historic Vermont Home

This historic 1860's home has been uniquely renovated to feature it's history combined with modern comfort. The kitchen is the focal place in the home which opens into the dining room. Watch the sunset from the back deck or while soaking in the hot tub! Original wood floors, tin ceilings, doors/door handles, etc. will take you back in time. This oasis in town provides back yard gardens and walking distance to downtown shops/restaurants.

Top guest favorite
Two Adirondack chairs are positioned on a well-manicured lawn, overlooking a serene landscape of grassy fields and scattered trees. A backdrop of rolling hills can be seen under a partly cloudy sky, evoking a sense of tranquility in a rural setting.
Guest suite in Cornwall
4.99 out of 5 average rating, 176 reviews

Home Suite Home in Cornwall, Minutes from Midd!

Looking for a home away from home on your travels in the Champlain Valley? Whether you're searching for a place to lay your head while visiting your Middlebury College student, a home base while exploring the gorgeous Green Mountain State, or a secluded, peaceful retreat in which to write the next chapter of your book, we've got just the spot! Our home, with the private guest suite and deck, is situated perfectly for your Vermont holiday.

Top guest favorite
Cabin in Ripton
5 out of 5 average rating, 86 reviews

Sauna @ Vermont Alpine Cabin

Unwind in your private sauna after skiing, hiking, or exploring Vermont’s Green Mountains. Vermont Alpine Cabin blends rustic charm with modern comfort for a deeply restorative stay. With a gentle peek-a-boo view of the mountains, this peaceful hideaway offers serenity, comfort, and a deep connection to nature. Discover calm, comfort, and Vermont charm — all tucked away in your very own private escape.

Top guest favorite
A newly renovated home showcases a green exterior with a metal roof. A welcoming front porch spans the width of the house, featuring multiple entry points and shaded by surrounding trees. A gravel driveway leads up to the home, offering ample outdoor space and a peaceful setting.
Home in Ripton
4.97 out of 5 average rating, 100 reviews

cozy home for a relaxing fall getaway

This newly Renovated Home has everything you will need to enjoy your stay with us. It’s a private home with 2 bedrooms, 2 bathrooms, full size washer and dryer, sitting area, cozy living room, spacious screen porch which is a great place to read or enjoy a meal, also a modern kitchen open to the dining room with a beautiful fireplace and sitting area.

Top guest favorite
A charming cottage is surrounded by a grassy area, featuring a red umbrella over a small outdoor table and chairs. Two white lounge chairs are positioned nearby, complemented by greenery and tall trees in the background.
Home in Middlebury
4.99 out of 5 average rating, 519 reviews

Nice one bedroom cottage

Located at the foot of the Green Mountains, a short walk to the Waybury Pub, nearby hiking, fishing and skiing. 4 miles to heart of Middlebury. Full kitchen, living room, bedroom(queen bed) and bathroom with stand up shower. High speed internet/hulu disney+ espn/washer-dryer/ac/ns

Popular amenities for Middlebury vacation rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Addison County
  5. Middlebury