Photo by David Alpert

Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Middlebury holiday rentals

Living area
Trout House Village Resort

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (19)
"Great updated cabin. "
United States
Diane
The price is S$247
includes taxes & fees
20 Dec - 21 Dec
Trout House Village Resort
Exterior
Robert Frost Mountain Cabins

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
The price is S$346
includes taxes & fees
5 Jan - 6 Jan, 2026
Robert Frost Mountain Cabins
Private kitchen
Bridges Resort

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
The price is S$318
includes taxes & fees
7 Jan - 8 Jan, 2026
Bridges Resort
Property grounds
16 Village Run... 2 Bedroom Condo by RedAwning

16 Village Run... 2 Bedroom Condo by RedAwning

16 Village Run... 2 Bedroom Condo by RedAwning
3.0 star property
Warren
The price is S$858
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

Middlebury Inn

Middlebury Inn

10/10 Excellent
" Clean room, nice amenities and staff and great restaurant"
Barbara 1-night trip
Posted 4 days ago
Middlebury 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.