Middlebury, VT Condo Rentals from AED 893

A wooden pier extending into a lake, surrounded by lush greenery and a prominent lighthouse on a small island.

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Our top choices for Middlebury condo rentals

A living room with a fireplace, a television mounted on the wall, and a balcony with outdoor furniture.

1. Out to Lunch trail ski-in/ski-out condo with balcony and heated pool

Warren

AED 1,054 total

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, and a bar area with stools.

2. Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio

Warren

Eric W.

AED 893 total

includes taxes & fees

4 Nov - 5 Nov

A wooden deck with a view of a forested mountain range.

3. The Bridges condo with forested views, three pools and two saunas

Warren

Michael L.

AED 1,235 total

includes taxes & fees

4 Nov - 5 Nov

A building with a wooden deck leading to a door marked 'Paradise.'

4. Condo with secure ski locker, study and central A/C, a half mile from Sugarbush

Warren

Anonymous traveler

AED 1,536 total

includes taxes & fees

4 Nov - 5 Nov

A residential building with a stone retaining wall, a grassy yard, and a swimming pool.

5. Ground-floor ski-in/ski-out condo with balcony and heated in-ground pool

Warren

Penney C.

AED 1,101 total

includes taxes & fees

17 Nov - 18 Nov

A covered outdoor seating area with wicker furniture and a table, overlooking a residential street.

6. Sugarbush Townhouse — Shuttle to the Slopes - Near Biking and Hiking Trails

Warren

AED 2,794 total

includes taxes & fees

17 Nov - 18 Nov

A spacious living room with a stone fireplace, wooden beams, large windows, and a cozy seating area.

7. Breathtaking Mountain Views Surround New Lakefront Condo

Hague

Christine M.

AED 1,435 total

includes taxes & fees

9 Nov - 10 Nov

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Top Middlebury Hotel Reviews

Courtyard Middlebury

10/10 Excellent

"This an independently owned location. Easy to get to. Good looking location. Good area. Place is very clean inside and outside. As far as Northern Vermont is concerned there is a lot of stores & restaurants in the immediate area however keep in mind Northern Vermont so most stuff will be closed by 8pm. If I go to this area again I would stay here again."

Super 8 by Wyndham Ticonderoga

10/10 Excellent

"The man at the front desk was so helpful with restaurant suggestions. The breakfast was small but at least we had something to start our day. This is right next to Walmart if you need something. It worked well for our party as we ended up needing two rooms on short notice. They were very accommodating."

Emrose Luxury Cabins

8/10 Good

"The cabins are new and well maintained. There are pots and pans and spatulas but incredibly no coffee maker. I don’t believe I’ve ever stayed in a room at any price point without a coffee maker. Also, the bed is up against a wall so you have to choose who has to crawl in and out of the bed to go to the bathroom, get a glass of water, etc. Not fun. There was also no contact information for management, so when we couldn’t figure out how to get the heater or fireplace working, we had to chat with Hotels.com who claimed our room did not have heat. Really? Vermont in the fall? Are you kidding me? After I almost lost my mind, they had someone from hotel management call me and instruct me how to turn the heat on. He was very nice and solved the problem, but how about providing contact information of someone on premises if there is an issue? The place is fairly new, and I like the concept, but they have a few things to iron out before they are ready for prime time. Let’s start with an $25 coffee maker in every room. Is that too much to ask? And Hotels.com really needs to get their chat proficiency together…."

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10/10 Excellent

"Wow, what a stay! We spent our honeymoon at this beautiful, cozy cabin, and it was the perfect romantic retreat. We loved cooking together, and the kitchen had absolutely everything we needed and more! The hot tub was perfect in the crisp autumn air, followed by snuggling up by the fire and watching a DVD.Thank you so much for such an unforgettable stay. We’ll definitely be back. This place has officially become a core memory for us!"

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Check prices for these dates

Our top choices for Middlebury condo rentals

1. Out to Lunch trail ski-in/ski-out condo with balcony and heated pool

2. Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio

3. The Bridges condo with forested views, three pools and two saunas

4. Condo with secure ski locker, study and central A/C, a half mile from Sugarbush

5. Ground-floor ski-in/ski-out condo with balcony and heated in-ground pool

6. Sugarbush Townhouse — Shuttle to the Slopes - Near Biking and Hiking Trails

7. Breathtaking Mountain Views Surround New Lakefront Condo

Find vacation rentals that suit your style

Top Middlebury Hotel Reviews

Courtyard Middlebury

Super 8 by Wyndham Ticonderoga

Emrose Luxury Cabins

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

White Horse Lodge

Cozy Loft for two with Hot Tub & Mtn Views

Lake Bomoseen Lodge

Swift House Inn

Frequently asked questions

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Search Condo Rentals in Middlebury

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlebury condo rentals

1. Out to Lunch trail ski-in/ski-out condo with balcony and heated pool

2. Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio

3. The Bridges condo with forested views, three pools and two saunas

4. Condo with secure ski locker, study and central A/C, a half mile from Sugarbush

5. Ground-floor ski-in/ski-out condo with balcony and heated in-ground pool

6. Sugarbush Townhouse — Shuttle to the Slopes - Near Biking and Hiking Trails

7. Breathtaking Mountain Views Surround New Lakefront Condo

Find vacation rentals that suit your style

Top Middlebury Hotel Reviews

Courtyard Middlebury

Frequently asked questions

Explore a world of travel with Expedia