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

Our top choices for Middlebury condo rentals

TV, fireplace, stereo
Inviting condo near skiing and golf, with fireplace and deck

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.
$253 nightly
The price is $283
Dec 22 - Dec 23
Total with taxes and fees
Inviting condo near skiing and golf, with fireplace and deck
Condo, 2 Bedrooms | Living area
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
$601 nightly
The price is $664
Dec 27 - Dec 28
Total with taxes and fees
16 Village Run... 2 Bedroom Condo by RedAwning
Fridge, oven, stovetop, dishwasher
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

Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
Warren
9.2 out of 10, Wonderful, (18)
"Great place"
United States
Jonathan M.
$282 nightly
The price is $316
Jan 12 - Jan 13, 2026
Total with taxes and fees
Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
Property grounds
Ski condo with locker, shuttle, fast WiFi, fireplace, washer/dryer & AC

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, (7)
"We enjoyed our stay at Paradise away very much. The apartment was spotless and well equipped and our whole family enjoyed the amenities nearby. The property is well maintained by caretakers who come by each morning to plow the parking lot after snowfalls and clear pathways. We would gladly stay here again."
United States
Paul F.
$442 nightly
The price is $495
Jan 14 - Jan 15, 2026
Total with taxes and fees
Ski condo with locker, shuttle, fast WiFi, fireplace, washer/dryer & AC
Fridge, microwave, oven, stovetop
Ski getaway near the slopes with private balcony & mountain views

Ski getaway near the slopes with private balcony & mountain views

Ski getaway near the slopes with private balcony & mountain views
Warren
8.8 out of 10, Excellent, (22)
"Ideally located for any season "
United States
Alison M.
$333 nightly
The price is $373
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ski getaway near the slopes with private balcony & mountain views
TV, video library
Ski-in/ski-out condo with mountain view, seasonal pool

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, (29)
"Easy to get in and parking."
United States
Richard H.
$334 nightly
The price is $374
Jan 12 - Jan 13, 2026
Total with taxes and fees
Ski-in/ski-out condo with mountain view, seasonal pool
TV, fireplace
Charming mountainside condo with fireplace, skiing, balcony, & washer/dryer

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

Charming mountainside condo with fireplace, skiing, balcony, & washer/dryer
Warren
7.6 out of 10, Good, (11)
"Super clean and comfortable home. Would definitely stay here again!"
United States
Stephanie P.
$296 nightly
The price is $332
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming mountainside condo with fireplace, skiing, balcony, & washer/dryer
Fireplace
Sugarbush Gem: Modern Ski Retreat near Slopes

Sugarbush Gem: Modern Ski Retreat near Slopes

Sugarbush Gem: Modern Ski Retreat near Slopes
Warren
9.0 out of 10, Wonderful, (40)
"Relaxing "
United States
Marianne
$439 nightly
The price is $491
Dec 27 - Dec 28
Total with taxes and fees
Sugarbush Gem: Modern Ski Retreat near Slopes
Exterior
Sugarbush Getaway – Comfortable Studio with Balcony & Value

Sugarbush Getaway – Comfortable Studio with Balcony & Value

Sugarbush Getaway – Comfortable Studio with Balcony & Value
2.0 star property
Warren
$395 nightly
The price is $442
Dec 22 - Dec 23
Total with taxes and fees
Sugarbush Getaway – Comfortable Studio with Balcony & Value
Terrace/patio
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

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.
$352 nightly
The price is $394
Jan 21 - Jan 22, 2026
Total with taxes and fees
Mountain-view condo with fireplace, 3 pools, hot tub, tennis & gym - near skiing
Exterior
Summer Haven Hideaway

Summer Haven Hideaway

Summer Haven Hideaway
Warren
8.8 out of 10, Excellent, (22)
"The condo was clean and stocked with convenience items. It was a close to the mountain and we were able to walk to the lifts. Overall great place!"
United States
Meghan L.
$487 nightly
The price is $546
Jan 5 - Jan 6, 2026
Total with taxes and fees
Summer Haven Hideaway
Condo, 1 Bedroom | Living area | Smart TV
Bridges 19 1 Bedroom Condo

Bridges 19 1 Bedroom Condo

Bridges 19 1 Bedroom Condo
3.0 star property
Warren
$584 nightly
The price is $636
Jan 13 - Jan 14, 2026
Total with taxes and fees
Bridges 19 1 Bedroom Condo
Smart TV, fireplace, books
Bridges Resort Condo with Pools, Hot Tub & Sugarbush Access

Bridges Resort Condo with Pools, Hot Tub & Sugarbush Access

Bridges Resort Condo with Pools, Hot Tub & Sugarbush Access
Warren
8.0 out of 10, Very Good, (1)
"There was lack of transparency about all the hot tubs being out of order and not available. Otherwise, the property was quiet and comfortable. "
United States
Melissa
$424 nightly
The price is $475
Jan 13 - Jan 14, 2026
Total with taxes and fees
Bridges Resort Condo with Pools, Hot Tub & Sugarbush Access
Smart TV, fireplace, books
Vermont Escape: Cozy Condo by Sugarbush Resort

Vermont Escape: Cozy Condo by Sugarbush Resort

Vermont Escape: Cozy Condo by Sugarbush Resort
Warren
$441 nightly
The price is $494
Jan 13 - Jan 14, 2026
Total with taxes and fees
Vermont Escape: Cozy Condo by Sugarbush Resort
Smart TV, books
Mountain condo w/ fireplace & covered porches

Mountain condo w/ fireplace & covered porches

Mountain condo w/ fireplace & covered porches
Warren
10.0 out of 10, Exceptional, (2)
"Great location in Sugarbush, all of the bedrooms had bathrooms and the place was great. I will look to staying there next time I go to Sugarbush. "
United States
William O.
$1,557 nightly
The price is $1,744
Dec 29 - Dec 30
Total with taxes and fees
Mountain condo w/ fireplace & covered porches
Property grounds
Ski-in/ski-out ground floor condo near slopes, balcony, fireplace, pool, wifi

Ski-in/ski-out ground floor condo near slopes, balcony, fireplace, pool, wifi

Ski-in/ski-out ground floor condo near slopes, balcony, fireplace, pool, wifi
Warren
$303 nightly
The price is $340
Jan 12 - Jan 13, 2026
Total with taxes and fees
Ski-in/ski-out ground floor condo near slopes, balcony, fireplace, pool, wifi
Interior
Charming 2BR/2BA Bridge-Level Condo at The Bridges Resort

Charming 2BR/2BA Bridge-Level Condo at The Bridges Resort

Charming 2BR/2BA Bridge-Level Condo at The Bridges Resort
2.0 star property
Warren
$665 nightly
The price is $745
Jan 8 - Jan 9, 2026
Total with taxes and fees
Charming 2BR/2BA Bridge-Level Condo at The Bridges Resort
Interior
Mountain condo w/ fireplace & winter ski access

Mountain condo w/ fireplace & winter ski access

Mountain condo w/ fireplace & winter ski access
Warren
9.8 out of 10, Exceptional, (10)
"Great and close to Sugarbush. Clean condo and ample space for family of 5"
United States
Doug M.
$655 nightly
The price is $734
Jan 7 - Jan 8, 2026
Total with taxes and fees
Mountain condo w/ fireplace & winter ski access
Condo, 3 Bedrooms | Living area | Smart TV
Club Sugarbush #8 3 Bedroom Condo

Club Sugarbush #8 3 Bedroom Condo

Club Sugarbush #8 3 Bedroom Condo
3.0 star property
Warren
$2,057 nightly
The price is $2,242
Dec 29 - Dec 30
Total with taxes and fees
Club Sugarbush #8 3 Bedroom Condo
Condo, 1 Bedroom | Living area | Smart TV
Glades 14 1 Bedroom Condo

Glades 14 1 Bedroom Condo

Glades 14 1 Bedroom Condo
3.0 star property
Warren
$624 nightly
The price is $680
Jan 13 - Jan 14, 2026
Total with taxes and fees
Glades 14 1 Bedroom Condo
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
"I didn’t have breakfast. The coolness of my room was fine."
Sam 1-night trip
Posted 3 days ago
Middlebury Inn

Find out more about Middlebury

Middlebury Condo Rentals information

Number of reviews
139
Accommodation
128 Condo Rentals
Lowest Price
$283
Highest Price
$2,242

Frequently asked questions

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How can I find cheap condos in Middlebury?
An excellent way to find cheap condos in Middlebury is with Expedia's user-friendly filter tool. Narrow down your search results by budget, star rating and amenities to grab awesome rates in just a few clicks.
What is there to do in Middlebury near my condo?
No matter your interests, Middlebury has tons of things to keep you going. National Museum of the Morgan Horse, UVM Morgan Horse Farm and Halpin Covered Bridge are on most travelers' sightseeing itineraries. You shouldn't miss Pulp Mill Covered Bridge, Otter Creek Brewing and Henry Sheldon Museum of Vermont History either. With Expedia's Middlebury condo deals, you can discover even more popular attractions like these with the money you save.

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