Photo by David Alpert

Search Holiday Rentals in Middlebury

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Check prices for these dates

Tonight
17 Dec - 18 Dec
Tomorrow
18 Dec - 19 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Middlebury holiday rentals

Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services
Trout House Village Resort

Cabin in Hague

Trout House Village Resort
3.0 star property
9.8 out of 10, Exceptional, (19)
"Great updated cabin. "
United States
Diane
The price is 3.939.538 ₫
5.031.163 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Trout House Village Resort
Exterior
Robert Frost Mountain Cabins

Cabin in Ripton

Robert Frost Mountain Cabins
3.5 star property
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
The price is 7.348.581 ₫
8.009.953 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Robert Frost Mountain Cabins
Condo, 2 Bedrooms (Standard) | Private kitchen
Bridges Resort

Condo resort in Warren

Bridges Resort
3.5 star property
8.2 out of 10, Very good, (16)
"Great condo and excellent proximity to sugarbush. 10/10 would rent again"
United States
Jesse
The price is 5.004.410 ₫
6.652.136 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Bridges Resort
Condo, 2 Bedrooms | Property grounds
16 Village Run... 2 Bedroom Condo by RedAwning

Condo in Warren

16 Village Run... 2 Bedroom Condo by RedAwning
3.0 star property
The price is 4.484.478 ₫
17.501.759 ₫ total
includes taxes & fees
27 Dec - 28 Dec
16 Village Run... 2 Bedroom Condo by RedAwning
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

Brandon Inn

Brandon Inn

10/10 Excellent
"A beautiful gem in downtown Brandon. Hotel is old but clean and well maintained. Great fun in the ballroom with the weekend pianist."
Pamela 1-night trip
Posted 5 days ago
Brandon Inn

Frequently asked questions

Are there holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Danforth Pewter, 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.

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 Kevin P. Mahaney '84 Center for the Arts and National Museum of the Morgan Horse, 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.