Middlebury vacation rentals

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Top-rated vacation rentals in Middlebury

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in New Haven

4.99 out of 5 average rating, 243 reviews

Small New Haven Cozy Cottage

This very small, compact cottage is in a rural setting, off the beaten path. It is about a 12 minute drive to Middlebury where you can find shops, restaurants and Middlebury College. Burlington is about 40 minutes north of where we are located. Hiking/skiing in the Green Mountains, fly fishing in the nearby New Haven River, boating/swimming on Lake Champlain, and enjoying the many local craft breweries and wineries are some of the many activities you have access to from this beautiful spot.

Jun 18 – 25

R1,561 ZAR per night

Guest favorite

Farm stay in Salisbury

4.95 out of 5 average rating, 271 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This adorable 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.

Sep 1 – 8

R2,462 ZAR per night

Guest favorite

Farm stay in Cornwall

4.93 out of 5 average rating, 203 reviews

Cozy country guest house

Our guesthouse is nestled in the Lemon Faire River Valley. This 1 bedroom with kitchen, bathroom, and extra sleeping loft gives you a quiet experience of the Vermont countryside. The outside entry deck overlooks over a 1000 acres of open field and farmland. Middlebury is only 3 miles away and offers museums, restaurants, and shopping. This is an active farm: horses, dogs, geese, a duck, and chickens. Please read the house manual as it has lots more information about the house and property.

Nov 12 – 19

R3,036 ZAR per night

Guest favorite

Apartment in Middlebury

5.0 out of 5 average rating, 169 reviews

Downtown 1 bedroom Apartment in Middlebury

Beautifully renovated upstairs apartment in the heart of downtown Middlebury, adjacent to Middlebury College, across from the Otter Creek Bakery and the new Middlebury town park. This charming space occupies 800 square feet above an optometry office in a Greek Revival home originally built circa 1856. It provides plenty of privacy and is within walking distance to all the restaurants and downtown shopping. A queen bed in the bedroom, and a pull out couch in the living room accommodates 4.

Jun 16 – 23

R4,070 ZAR per night

Guest favorite

Apartment in Middlebury

5.0 out of 5 average rating, 185 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.

Jun 27 – Jul 4

R9,977 ZAR per night

Guest favorite

Cottage in New Haven

4.99 out of 5 average rating, 148 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.

Feb 3 – 10

R2,968 ZAR per night

Guest favorite

Yurt in New Haven

4.91 out of 5 average rating, 254 reviews

Song Bird Sangha Yurt

Songbird Sangha was thoughtfully created to provide a peaceful retreat from the world. It is nestled into a beautiful forest with privacy in mind. You will fall in love with the sky dome over your queen sized bed for the most comfortable star gazing ever! Your stay would not be complete without a complimentary campfire & marshmallow and if you would like more magic sign up for our Airbnb Experience The Healing Nature of Horses, a life enhancing encounter . Certified Wildlife Habitat.

Aug 2 – 9

R2,355 ZAR per night

Guest favorite

Condo in Vergennes

4.96 out of 5 average rating, 178 reviews

Little Brick House Off Main (Apt. B)

Bright, clean and cozy second-floor apartment located just steps to restaurants, bars, cafes, and shopping in the heart of historic downtown Vergennes. This convenient location is a 35-minute drive to Burlington and just 20 mins to Middlebury. A 10-minute drive to nearby Button Bay Park and Basin Harbor Resort on the shores of Lake Champlain. 35-minute drive to Mad River Glen Ski Area, 50-minute drive to Sugarbush Resort, and just 35 minutes to the Middlebury Snow Bowl.

Sep 7 – 14

R2,076 ZAR per night

Guest favorite

Apartment in Vergennes

4.98 out of 5 average rating, 314 reviews

Downtown Vergennes Art House/Glass Studio

Located right in downtown Vergennes, this home of a local kilnforming glass artist houses her collection of artwork--her own, work of friends and favorite artists, and also her own glass studio. It is steps away from fantastic local eateries, a brew pub and cidery, the beauty and power of the Otter Creek River and Falls, the Vergennes Opera House. Middlebury is a 20 minute drive, Burlington, 40. Straight shots on Route 7. About the same on beautiful back roads.

Mar 29 – Apr 5

R2,220 ZAR per night

Guest favorite

Apartment in Middlebury

4.99 out of 5 average rating, 103 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.

Jun 15 – 22

R3,459 ZAR per night

Guest favorite

Guest suite in Cornwall

4.99 out of 5 average rating, 128 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.

Aug 27 – Sep 3

R2,798 ZAR per night

Guest favorite

Home in Middlebury

4.99 out of 5 average rating, 355 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

Nov 6 – 13

R2,472 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middlebury vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Middlebury's top sights

Fire & Ice53 locals recommend

Rosie's18 locals recommend

A&W6 locals recommend

Two Brothers Tavern64 locals recommend

Mister Up's Restaurant & Pub20 locals recommend

Middlebury College43 locals recommend

Other great vacation rentals in Middlebury

Guest favorite

Cabin in Bristol

4.86 out of 5 average rating, 173 reviews

Colonel's Camp in Buck Haven

Apr 3 – 10

R2,235 ZAR per night

Guest favorite

Apartment in Hancock

4.95 out of 5 average rating, 146 reviews

Suite in the Green Mountains

Apr 12 – 19

R1,733 ZAR per night

Guest favorite

Apartment in Bristol

4.91 out of 5 average rating, 119 reviews

Peaceful Getaway in Bristol Village.

Jul 26 – Aug 2

R1,945 ZAR per night

Guest favorite

Yurt in Bristol

4.93 out of 5 average rating, 237 reviews

Bristol Cozy Yurt near Hiking/Swimming|Maple Farm

Dec 21 – 28

R2,424 ZAR per night

Guest favorite

Home in Ripton

4.89 out of 5 average rating, 257 reviews

Cozy cottage near nature

Aug 25 – Sep 1

R2,536 ZAR per night

Guest favorite

Cabin in Bristol

4.95 out of 5 average rating, 109 reviews

Cozy Cabin on the River in Bristol

Sep 8 – 15

R3,175 ZAR per night

Guest favorite

Apartment in Middlebury

4.85 out of 5 average rating, 140 reviews

Cozy Apt. Near heart of Middlebury Fiber WIFI

Dec 31 – Jan 7

R2,986 ZAR per night

Guest favorite

Loft in New Haven

4.98 out of 5 average rating, 247 reviews

Sunrise over South Mountain

Jul 7 – 14

R3,505 ZAR per night

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Other great vacation rentals in Middlebury

Guest favorite

Home in Leicester

4.98 out of 5 average rating, 135 reviews

Luxurious Cottage Massage Therapy Studio On Site

Aug 14 – 21

R3,384 ZAR per night

Guest favorite

Guesthouse in Monkton

4.98 out of 5 average rating, 106 reviews

Beautiful, 1 BR guesthouse

Jan 8 – 15

R2,603 ZAR per night

Guest favorite

Apartment in New Haven

4.99 out of 5 average rating, 144 reviews

Gracious two bedroom just minutes to Middlebury!

Mar 27 – Apr 3

R4,163 ZAR per night

Guest favorite

Home in Middlebury

4.9 out of 5 average rating, 152 reviews

Entire House in Middlebury - Walk Everywhere

Oct 8 – 15

R7,261 ZAR per night

Superhost

Apartment in Bristol

4.86 out of 5 average rating, 118 reviews

Overlook at the Office

Nov 20 – 27

R1,335 ZAR per night

Guest favorite

Guest suite in Hinesburg

4.96 out of 5 average rating, 1117 reviews

Boston Magazine Pick! Barn Loft

Sep 5 – 12

R3,046 ZAR per night

Guest favorite

Cottage in Lincoln

4.87 out of 5 average rating, 858 reviews

The Barn at North Orchard, Near Middlebury

Mar 24 – 31

R2,376 ZAR per night

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 395 reviews

Black haus: a hip, cool house hidden in a forest.

Mar 17 – 24

R2,582 ZAR per night

Show all

Quick stats about vacation rentals in Middlebury

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
3.5K reviews
Nightly prices starting at
R1,296 ZAR before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Middlebury?
Yes! Work meets play with ease at over 30 vacation rentals in Middlebury featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Middlebury?
Four-legged friends are welcome in Middlebury. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Middlebury have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Middlebury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middlebury have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Middlebury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middlebury have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Middlebury. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Middlebury?
Middlebury has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Middlebury?
Experience the best of Middlebury with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Apartment Rentals in Middlebury?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Middlebury vacation rentals

Top-rated vacation rentals in Middlebury

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Middlebury vacation rentals

Stay near Middlebury's top sights

Other great vacation rentals in Middlebury

Cabin in Bristol

Apartment in Hancock

Apartment in Bristol

Yurt in Bristol

Home in Ripton

Cabin in Bristol

Apartment in Middlebury

Loft in New Haven

Other great vacation rentals in Middlebury

Home in Leicester

Guesthouse in Monkton

Apartment in New Haven

Home in Middlebury

Apartment in Bristol

Guest suite in Hinesburg

Cottage in Lincoln

Cabin in Rochester

Quick stats about vacation rentals in Middlebury

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Middlebury?

Are there pet-friendly vacation rentals in Middlebury?

Do house rentals in Middlebury have a bbq area?

Do house rentals in Middlebury have wireless internet?

Do house rentals in Middlebury have air conditioning?

Are there family-friendly house rentals in Middlebury?

How much does it cost to stay in apartment rentals in Middlebury?

What are the most popular amenities for Apartment Rentals in Middlebury?

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