Holiday rentals in Middlebury

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Top-rated holiday rentals in Middlebury

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Guest favourite

Cottage in New Haven

4.99 out of 5 average rating, 241 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.

18–25 Jun

₹7,375 per night

Guest favourite

Flat in Bristol

4.91 out of 5 average rating, 116 reviews

Peaceful Getaway in Bristol Village.

Simple beauty, generous space and peace, in a second floor one bedroom guest apartment with bathtub, shower and galley kitchen without stove. Double futon in living area for additional guests. A very sweet private getaway for a couple, or group of friends or small family. Bristol is a true New England find with an active arts community, good restaurants and shops, as well as several yoga and tai chi instructional groups. Settle your energy here and enjoy life. Skiing and hiking nearby.

9–16 Aug

₹9,211 per night

Guest favourite

Farm stay in Cornwall

4.93 out of 5 average rating, 201 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.

20–27 Dec

₹13,858 per night

Guest favourite

Flat 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.

4–11 Sep

₹18,360 per night

Guest favourite

Flat in Middlebury

5.0 out of 5 average rating, 183 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.

25 Mar – 1 Apr

₹45,009 per night

Guest favourite

Cottage in New Haven

4.99 out of 5 average rating, 147 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.

10–17 Feb

₹13,391 per night

Guest favourite

Yurt in Bristol

4.93 out of 5 average rating, 235 reviews

Bristol Cozy Yurt near Skiing/Hiking|Maple Farm

Our cozy yurt is located within minutes of amazing, hiking, biking, swimming, skiing, breweries and much more! Sit around the campfire while listening to our resident owls or stare up at the stars through the dome. We're centrally located to some of the best hiking, biking and swimming in North Central Vermont. We're also close to civilization with several small towns within 15 minutes to explore for food, drink, art, and shopping. Or travel a bit further to Burlington..

1–8 Dec

₹8,968 per night

Guest favourite

Apartment in Vergennes

4.97 out of 5 average rating, 174 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.

16–23 Aug

₹8,831 per night

Guest favourite

Flat in Middlebury

4.99 out of 5 average rating, 100 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.

4–11 Jul

₹15,604 per night

Guest favourite

Loft in New Haven

4.98 out of 5 average rating, 244 reviews

Sunrise over South Mountain

This is a spacious guesthouse/retreat where you can relax and unwind. There are great views and walking down the road is serene, with open fields bordered by woods and teaming with wildlife. In the winter you can Nordic ski or snowshoe right outside your door, through fields and woodland paths down by an active sugar-bush. We currently have chickens as well as my friendly dog Annie who loves to play. We also have a young kitty named LB who is a pip.

16–23 Apr

₹11,741 per night

Guest favourite

Guest suite in Cornwall

4.99 out of 5 average rating, 126 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.

27 Aug – 3 Sep

₹11,871 per night

Guest favourite

Home in Middlebury

4.99 out of 5 average rating, 351 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

7–14 May

₹10,966 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Middlebury holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

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 holiday rentals in Middlebury

Guest favourite

Farm stay in Salisbury

4.95 out of 5 average rating, 265 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

7–14 Dec

₹10,936 per night

Guest favourite

Yurt in New Haven

4.91 out of 5 average rating, 254 reviews

Song Bird Sangha Yurt

30 Aug – 6 Sep

₹10,623 per night

Guest favourite

Cabin in Bristol

4.86 out of 5 average rating, 172 reviews

Colonel's Camp in Buck Haven

15–22 Aug

₹10,536 per night

Guest favourite

Home in Ripton

4.89 out of 5 average rating, 255 reviews

Cozy cottage near nature

19–26 Sep

₹11,441 per night

Guest favourite

Flat in Bristol

4.88 out of 5 average rating, 285 reviews

"Dragonfly Apartment" Private Bristol Apartment

9–16 Nov

₹7,501 per night

Guest favourite

Barn in Ripton

4.93 out of 5 average rating, 141 reviews

Green Mountains Vermont Middlebury Bread Loaf Barn

21–28 Mar

₹13,245 per night

Guest favourite

Home in Leicester

4.98 out of 5 average rating, 132 reviews

Luxurious Cottage Massage Therapy Studio On Site

18–25 Nov

₹14,294 per night

Guest favourite

Cabin in Bristol

4.95 out of 5 average rating, 105 reviews

Cozy Cabin on the River in Bristol

3–10 Mar

₹14,580 per night

Show all

Quick stats about holiday 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	3.5T reviews
Nightly prices starting at	₹5,846 before taxes and fees

Holiday rentals in Middlebury

Top-rated holiday rentals in Middlebury

Cottage in New Haven

Flat in Bristol

Farm stay in Cornwall

Flat in Middlebury

Flat in Middlebury

Cottage in New Haven

Yurt in Bristol

Apartment in Vergennes

Flat in Middlebury

Loft in New Haven

Guest suite in Cornwall

Home in Middlebury

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Middlebury holiday rentals

Stay near Middlebury's top sights

Other great holiday rentals in Middlebury

Farm stay in Salisbury

Yurt in New Haven

Cabin in Bristol

Home in Ripton

Flat in Bristol

Barn in Ripton

Home in Leicester

Cabin in Bristol

Quick stats about holiday rentals in Middlebury

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore