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Middlebury Vacation Rentals

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Vacation Rentals in Middlebury

Microwave, oven, stovetop, dishwasher
Downtown Middlebury River House

Downtown Middlebury River House

Middlebury
10.0 out of 10, Exceptional, (8)
"Great place right near downtown "
United States
Chris H.
$1,123 nightly
The price is $1,269
Dec 28 - Dec 29
Total with taxes and fees
Downtown Middlebury River House
Property grounds
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, (2)
"Super cute and cozy! It was perfect."
United States
Sarah D.
$149 nightly
The price is $167
Dec 9 - Dec 10
Total with taxes and fees
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services
Trout House Village Resort

Trout House Village Resort

3.0 star property
Hague
9.8 out of 10, Exceptional, (18)
"Very friendly owner and beautiful views"
United States
Anthony
$189 nightly
The price is $210
Dec 8 - Dec 9
Total with taxes and fees
Trout House Village Resort
Property grounds
Cozy A-frame with loft, deck and easy ski access

Cozy A-frame with loft, deck and easy ski access

Waitsfield
7.6 out of 10, Good, (7)
"The property had plenty of space for our group. I would suggest some steps be put in and some more care be spent on snow removal but we had fun sliding downhill to the entrance."
United States
Jason F.
$423 nightly
The price is $474
Dec 8 - Dec 9
Total with taxes and fees
Cozy A-frame with loft, deck and easy ski access
Outdoor dining
Cozy Tiny Home in charming Bristol VT, close to major ski areas

Cozy Tiny Home in charming Bristol VT, close to major ski areas

Bristol
9.8 out of 10, Exceptional, (15)
"Great spot for 1-2 people and maybe a child. It was clean and affordable and had everything you need. "
United States
David G.
$147 nightly
The price is $164
Dec 8 - Dec 9
Total with taxes and fees
Cozy Tiny Home in charming Bristol VT, close to major ski areas
Fridge, microwave, oven, stovetop
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, (67)
"Superb lodging. Enjoyed the cosmopolitan vibe in a rural setting. "
United States
Jason R.
$150 nightly
The price is $168
Dec 8 - Dec 9
Total with taxes and fees
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Fridge, microwave, oven, stovetop
Mountain-view condo with fireplace, 3 pools, hot tub, tennis & gym - near skiing

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

Warren
8.8 out of 10, Excellent, (15)
"We travel to the area every year for the VT Gran Fondo and love staying at bridges. The amenities are wonderful for families."
United States
LILIA R.
$298 nightly
The price is $334
Dec 8 - Dec 9
Total with taxes and fees
Mountain-view condo with fireplace, 3 pools, hot tub, tennis & gym - near skiing
Exterior
Robert Frost Mountain Cabins

Robert Frost Mountain Cabins

3.5 star property
Ripton
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
$276 nightly
The price is $301
Jan 4 - Jan 5, 2026
Total with taxes and fees
Robert Frost Mountain Cabins
Smart TV
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, (38)
"Very nice updated home with charming amenities, close to Waitsfield central. Clean and spacious for our party of 3 adults. "
United States
Leann
$309 nightly
The price is $346
Dec 8 - Dec 9
Total with taxes and fees
Go Skiing or Hiking from an Enchanting, Light-Filled Home
Condo, 2 Bedrooms | Property grounds
16 Village Run... 2 Bedroom Condo by RedAwning

16 Village Run... 2 Bedroom Condo by RedAwning

3.0 star property
Warren
$551 nightly
The price is $610
Dec 27 - Dec 28
Total with taxes and fees
16 Village Run... 2 Bedroom Condo by RedAwning
Condo, 2 Bedrooms (Standard) | Private kitchen
Bridges Resort

Bridges Resort

3.5 star property
Warren
8.2 out of 10, Very Good, (16)
"Great condo and excellent proximity to sugarbush. 10/10 would rent again"
United States
Jesse
$192 nightly
The price is $209
Dec 14 - Dec 15
Total with taxes and fees
Bridges Resort
Exterior
Beautiful brand new cabin one minute from Sugarbush Resort

Beautiful brand new cabin one minute from Sugarbush Resort

Warren
10.0 out of 10, Exceptional, (15)
"We had a great time - pool and hot tub were a blast for the kids! "
United States
Sheila Dillon W.
Beautiful brand new cabin one minute from Sugarbush Resort
Fridge, microwave, oven, stovetop
The Bomoseen Bungalow: Vermont Lake House with Private Dock

The Bomoseen Bungalow: Vermont Lake House with Private Dock

2.0 star property
Bomoseen
9.6 out of 10, Exceptional, (4)
"Nice place to stay. Very well equipped and clean."
United States
Rich S.
$486 nightly
The price is $545
Dec 8 - Dec 9
Total with taxes and fees
The Bomoseen Bungalow: Vermont Lake House with Private Dock
Property grounds
Inviting condo near skiing and golf, with fireplace and deck

Inviting condo near skiing and golf, with fireplace and deck

Warren
8.8 out of 10, Excellent, (10)
"Location, close to everything"
United States
Dave D.
$220 nightly
The price is $246
Dec 8 - Dec 9
Total with taxes and fees
Inviting condo near skiing and golf, with fireplace and deck
Fireplace, books
Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook

Warren
9.8 out of 10, Exceptional, (159)
"Great location and a great price. Perfect for 2-4 people who just want to get away to the peace of Vermont."
United States
James N.
$390 nightly
The price is $437
Dec 8 - Dec 9
Total with taxes and fees
Stetson Hollow Cabin by Stetson Brook
Outdoor dining
Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony

Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony

Warren
8.4 out of 10, Very Good, (74)
"Perfect summer getaways! The condo was comfortable and in a great location. The pools and rec center were also so much fun. Looking forward to coming back next year."
United States
Christine P.
$180 nightly
The price is $202
Dec 14 - Dec 15
Total with taxes and fees
Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony
Fridge, microwave, oven, stovetop
Lovely cabin nestled in the woods one minute from Sugarbush Resort

Lovely cabin nestled in the woods one minute from Sugarbush Resort

Warren
9.8 out of 10, Exceptional, (21)
"Great dog freindly cabin. Love the hot tub! Just as good as the first time,"
United States
Jack G.
Lovely cabin nestled in the woods one minute from Sugarbush Resort
Property grounds
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Warren
10.0 out of 10, Exceptional, (22)
"Fantastic house in a beautiful setting. Just right for the area and the kind of trip we were hoping to have. Colin is a great host as well."
United States
kevin m.
Beautiful home located in the Mad River Valley
Private kitchen
The Hideaway

The Hideaway

Hinesburg
9.4 out of 10, Exceptional, (8)
"Very cute, clean and well-appointed place to stay. Its in a small town south of Burlington with a lot of charm, pastoral views and a great grocery store. It was just what we needed, and the hosts have put a lot of care into the apartement."
United States
Karen P.
$150 nightly
The price is $168
Dec 9 - Dec 10
Total with taxes and fees
The Hideaway
Property grounds
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Warren
9.2 out of 10, Wonderful, (7)
"Good area"
United States
Dakota N.
Beautiful home located in the Mad River Valley
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

Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"Very comfortable bed. Clean room"
Josephine 2-night trip
Posted 3 days ago
Courtyard Middlebury

Find out more about Middlebury

Everything you need to know about Middlebury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebury vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middlebury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $168 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Middlebury?

Yes, we offer vacation rentals in Middlebury close to Danforth Pewter, or you can select a more remote option if you want a relaxing stay. Our travelers 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 vacation home rentals that Middlebury has to offer?

Lake George Waterfront Paradise Dock Slip: Visitors like this Middlebury vacation home rental. It is located on the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family.

How many vacation rentals are there in Middlebury?

Expedia has 12 vacation rentals for your stay in Middlebury.

What’s there to see and do in Middlebury?

Cultural attractions include Town Hall Theater and Henry Sheldon Museum of Vermont History, 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 vacation rental in Middlebury like?

Vacation rentals are private properties you can stay in for a couple of days or more in Middlebury. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips.