Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

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Guest favorite
The interior of the yurt showcases a high, curved ceiling with wooden beams and a central dome allowing natural light. A cozy seating area with a sofa is positioned near a rocking chair, while a dining table for four is set against the wall. A staircase leads to the sleeping area.
Farm stay in Bristol
4.91 out of 5 average rating, 104 reviews

Private constructed yurt on organic farm

Take it easy at this unique and tranquil getaway. The entire constructed yurt is yours to enjoy privately. Nestled on an organic farm, it sits a bit above Bristol offering sweeping views of the valley and the beautiful Adirondack mountains. There are many farm animals on the property and farm tours are available upon request. PLEASE NOTE: The queen bed is only accessible by a ladder. The property is located up a steep driveway. During the winter months all wheel drive vehicles are required.

Top guest favorite
A spacious living area features a queen size bed with a blue quilt, adjacent to a cozy fireplace. Green armchairs and a small round table provide additional seating. Tall curtains frame windows, and a bookshelf adds a touch of color to the wall.
Apartment in Middlebury
4.99 out of 5 average rating, 166 reviews

Bluebird Studio- Light filled and airy

This studio apartment attached to the main house has a style all its own. Contemporary design with high ceilings, clerestory windows and a skylight. Spaces include a large Living Room/Bedroom, Kitchen/Dining area, bathroom with a step-in shower and an adjoining Dressing Room with vanity and sink. There is also an outdoor covered space to enjoy. Furniture includes a Queen size bed, 3 comfy chairs, small round table and 4 chairs. Location is a bit more than one mile from downtown Middlebury.

Guest favorite
The exterior of a charming cottage apartment is surrounded by vibrant orange flowers and lush greenery. Large windows reflect natural light, and a covered porch provides a shaded area. Mature trees add to the welcoming atmosphere of the property.
Apartment in Middlebury
4.91 out of 5 average rating, 125 reviews

The Cottage Apartment in downtown Middlebury.

This charming, 1st floor two-bdr. cottage apartment is steps from Main Street, downtown Middlebury, & walking distance to shops, restaurants, and the College. An historic college town, Middlebury is replete with great restaurants, shops and cultural events to enjoy, all within walking distance. The comforts of this home include private parking, gardens, separate entrance, full kitchen and bath, and sleeps four. It is only a half hour from The Middlebury College Snow Bowl, and Lake Champlain.

Top guest favorite
A spacious grassy yard is framed by trees, leading to distant views of mountains under a partly cloudy sky. A set of wooden chairs is positioned on the lawn, offering a peaceful spot to relax. The corner of a building with stairs is visible in the foreground.
Farm stay in Cornwall
4.95 out of 5 average rating, 139 reviews

Orchard Guesthouse - 1 mile to Middlebury

Orchard Guesthouse on our apple orchard is a delightfully unique place to stay. A former pickers cottage, we offer dorm style bedrooms and bathrooms with a rustic yet cozy interior. Includes full use of the house and adjacent yard. We are conveniently located 2 miles from Middlebury and 1 mile from Middlebury College campus. Come enjoy a full range of outdoor activities, adventure is on your doorstep! Perfect set up for groups - cycling, hiking, skiing (nordic/alpine) or college events.

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, 211 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
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
4.97 out of 5 average rating, 180 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
The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.
Farm stay in Salisbury
4.95 out of 5 average rating, 406 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Top guest favorite
A bright living area is highlighted by large glass doors and windows that allow abundant natural light. Comfortable seating arrangements include a gray sofa and a wooden coffee table. A dining area with a white table and chairs is positioned in the background, complemented by indoor plants.
Home in Middlebury
5 out of 5 average rating, 101 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, 152 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
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, 169 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
An updated kitchen space is presented with a central wooden island and three tall chairs. Exposed brick and wooden beams complement modern cabinetry. Natural light floods the area through a nearby window, revealing a view of the outside.
Home in Middlebury
5 out of 5 average rating, 162 reviews

In the heart of Middlebury, a modern farmhouse

This beautifully RENOVATED 3BR, 1.5 bath home merges its FARMHOUSE HERITAGE with MODERN décor and comforts. It is perfectly located on SOUTH STREET, perhaps the most sought-after address in Middlebury because it is nestled right between the heart of campus and this quintessential New England town. Both are just under a 5 min walk away.

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 East Middlebury
4.99 out of 5 average rating, 486 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. ethernet connection/cable tv/washer-dryer/ac/ns

Popular amenities for Middlebury vacation rentals

When is the best time to visit Middlebury?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$38,066 GYDG$43,504 GYDG$37,229 GYDG$36,602 GYDG$42,458 GYDG$43,922 GYDG$40,785 GYDG$42,458 GYDG$39,739 GYDG$42,249 GYDG$36,602 GYDG$34,092 GYD
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Quick stats about vacation rentals in Middlebury

  • Total vacation rentals

    Explore 70 vacation rentals in Middlebury

  • Nightly prices starting at

    Middlebury vacation rentals start at G$14,641 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,100 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Middlebury vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Middlebury rentals

  • 4.9 Average rating

    Middlebury stays are highly rated by guests—averaging 4.9 out of 5!

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