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Our top choices for Middlebury holiday rentals

Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage in the heart of Middlebury!
Middlebury
The price is £265
includes taxes & fees
18 May - 19 May
Purple Door Cottage in the heart of Middlebury!

*Downtown Middlebury Waterfall Studio Apartment*

*Downtown Middlebury Waterfall Studio Apartment*
Middlebury
9.8 out of 10, Exceptional, (10 reviews)
"fantastic!"
United States
Diana L.
The price is £235
includes taxes & fees
20 May - 21 May
*Downtown Middlebury Waterfall Studio Apartment*

Downtown Middlebury 3 BR Home - Walk Everywhere!

Downtown Middlebury 3 BR Home - Walk Everywhere!
Middlebury
9.6 out of 10, Exceptional, (31 reviews)
"Great location, very clean"
United States
Karyn M.
The price is £271
includes taxes & fees
26 May - 27 May
Downtown Middlebury 3 BR Home - Walk Everywhere!

Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
10.0 out of 10, Exceptional, (4 reviews)
"All was so nice. The bed the coziness the cleanliness the location. "
United States
Sara B.
The price is £126
includes taxes & fees
19 May - 20 May
Glamping hut with WiFi in Ripton, biking, hiking, skiing

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (167 reviews)
"Perfect spot for our 3 day ski trip. Very nice and cozy cabin! Quiet area and the owners were great with making sure all was good. "
United States
Jeffrey C.
The price is £326
includes taxes & fees
17 May - 18 May
Stetson Hollow Cabin by Stetson Brook

Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village
East Warren
9.6 out of 10, Exceptional, (17 reviews)
"Loved the property. Clean, modern, great location."
United States
Richard
The price is £304
includes taxes & fees
15 May - 16 May
Dreamy Artist Chalet in Secluded Historic Village

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (41 reviews)
"Very nice place great owner"
United States
Joe
The price is £207
includes taxes & fees
18 May - 19 May
Robert Frost Mountain Cabins

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, nice amenities!"
United States
Aba E.
The price is £126
includes taxes & fees
25 May - 26 May
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio

Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
Warren
9.4 out of 10, Exceptional, (23 reviews)
"Enjoyable stay"
United States
Eric W.
The price is £188
includes taxes & fees
17 May - 18 May
Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (22 reviews)
"spotless room w an incredible view!"
United States
Joanne
The price is £141
includes taxes & fees
31 May - 1 Jun
Trout House Village Resort

Charming mountainside condo with fireplace, skiing, balcony, & washer/dryer

Charming mountainside condo with fireplace, skiing, balcony, & washer/dryer
Warren
8.0 out of 10, Very good, (13 reviews)
"The place was charming and very comfortable to live in for a few days. The balcony kind of makes the place special. At night you can sit outside and watch the snow cats grooming the trails in tranquil peace. The gas fireplace was also spot on. A perfect place to stay while at Sugarbush "
United States
James M.
The price is £216
includes taxes & fees
16 May - 17 May
Charming mountainside condo with fireplace, skiing, balcony, & washer/dryer

Ski condo with locker, shuttle, fast WiFi, fireplace, washer/dryer & AC

Ski condo with locker, shuttle, fast WiFi, fireplace, washer/dryer & AC
Warren
9.0 out of 10, Wonderful, (14 reviews)
"The condo was great, very clean and spacious, and well-stocked with blankets, towels, utensils etc. Having the gas fireplace was very nice, as it was extremely cold during our stay. The location was fantastic, it was a quick two-minute drive to the Sugarbush parking lot, and close to Warren's restaurants and other amenities. "
United States
Anonymous traveller
The price is £325
includes taxes & fees
15 May - 16 May
Ski condo with locker, shuttle, fast WiFi, fireplace, washer/dryer & AC

Go Skiing or Hiking from an Enchanting, Light-Filled Home

Go Skiing or Hiking from an Enchanting, Light-Filled Home
Waitsfield
9.8 out of 10, Exceptional, (46 reviews)
"Excellent Location ! "
United States
Luke A.
The price is £257
includes taxes & fees
15 May - 16 May
Go Skiing or Hiking from an Enchanting, Light-Filled Home

Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is £255
includes taxes & fees
17 May - 18 May
Adorable cabin with screened porch and private fire pit

Mountain-view condo with fireplace, 3 pools, tennis & gym - near skiing

Mountain-view condo with fireplace, 3 pools, tennis & gym - near skiing
Warren
8.8 out of 10, Excellent, (18 reviews)
"Great location near Sugarbush. Clean and quiet."
United States
Cynthia
The price is £234
includes taxes & fees
17 May - 18 May
Mountain-view condo with fireplace, 3 pools, tennis & gym - near skiing

Ski getaway near the slopes with private balcony & mountain views

Ski getaway near the slopes with private balcony & mountain views
Warren
9.0 out of 10, Wonderful, (29 reviews)
"Super easy access to ski, there is a shuttle but we walked because it’s so close. Nice room, plenty of linens, clean kitchen. "
United States
Stefani K.
The price is £219
includes taxes & fees
18 May - 19 May
Ski getaway near the slopes with private balcony & mountain views

Ski-in/ski-out condo with mountain view, seasonal pool

Ski-in/ski-out condo with mountain view, seasonal pool
Warren
8.4 out of 10, Very good, (34 reviews)
"Cozy and convenient. "
United States
Allie S.
The price is £223
includes taxes & fees
15 May - 16 May
Ski-in/ski-out condo with mountain view, seasonal pool

Unique family-friendly Vermont cabin!

Unique family-friendly Vermont cabin!
Fair Haven
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay at a new and clean cabin. It was very cozy!"
United States
Emily J.
The price is £218
includes taxes & fees
17 May - 18 May
Unique family-friendly Vermont cabin!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlebury Hotel Reviews

Find out more about Middlebury

Everything you need to know about Middlebury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebury holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlebury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebury. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlebury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Kevin P. Mahaney '84 Center for the Arts, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Middlebury has a good selection of restaurants. Make sure you have time to check out the architecture and university setting during your trip.

What are some of the best holiday rentals that Middlebury has to offer?

Water front home with large two tiered deck! 2 bathrooms 😂: This holiday home rental outside of Middlebury is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Middlebury?

Expedia has 13 holiday rentals for your stay in Middlebury.

What’s there to see and do in Middlebury?

Cultural attractions include Henry Sheldon Museum of Vermont History and Kevin P. Mahaney '84 Center for the Arts, whereas Green Mountain National Forest and Middlebury Falls are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include UVM Morgan Horse Farm and Halpin Covered Bridge.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.