Middlebury Chalets from CA $546

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Middlebury chalets

A wooden deck with a view of a forested hillside.

1. Handcrafted Vermont Chalet • Walk to Lake • Fire Pit • Private Deck • AC

East Warren

Beth Y.

CA $546 total

includes taxes & fees

Nov 1 - Nov 2

A cabin with a sloped roof, large windows, and a snow-covered ground.

2. Magnificent any time of year

East Warren

Sheila

CA $583 total

includes taxes & fees

Nov 9 - Nov 10

A cabin surrounded by a forest with snow on the ground.

3. Dreamy Artist Chalet in Secluded Historic Village

East Warren

Jonathan B.

CA $669 total

includes taxes & fees

Nov 1 - Nov 2

A wooden deck with a view of a forest and a mountain.

4. Handcrafted Log Cabin • Walk to Lake • Private Backyard w/Fire Pit • Sleeps 8

East Warren

Greg E.

CA $1,061 total

includes taxes & fees

Oct 27 - Oct 28

View all properties

Find vacation rentals that suit your style

Cottages

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Top Middlebury Hotel Reviews

The Warren Lodge

10/10 Excellent

"Perfect little place with great backyard and walking paths. The staff was also super responsive and helpful."

Lake Bomoseen Lodge

10/10 Excellent

"We stayed in room 106 Room, Lake View (Lodge). It was perfect. Super easy checkin, exceptionally clean room, well maintained property, and we had an amazing view. The Lodge has a fantastic Tap Room with a fantastic menu that seems to be loved by both the locals and tourist which say a lot! The property offers everything you could want/need in any season. I would highly recommend and will return! Excellent stay!"