Search Middlebury Cottage Rentals from CA $179

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Middlebury cottages

A two-story brick house with a white garage door, surrounded by a well-maintained lawn and a tree.

1. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is CA $381
CA $753 total
includes taxes & fees
Nov 7 - Nov 8
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

2. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
The price is CA $179
CA $290 total
includes taxes & fees
Nov 17 - Nov 18
Serene Country Cottage
A two-story house with a dock extending into a lake, surrounded by trees with autumn foliage.

3. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is CA $342
CA $682 total
includes taxes & fees
Nov 18 - Nov 19
Escape to Bantam Lake- With Fireplace and Hot tub!
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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Learn more about Middlebury

Quassy Amusement Park offers thrilling rides and a refreshing lakeside beach where families cool off during summer months. History buffs can explore the 1800s buildings at Middlebury Historical Society Museum, while hikers enjoy scenic trails through Hop Brook Lake Park.

See all hotels in Middlebury
A multi-tiered waterfall cascading over dark rocks surrounded by lush greenery.

Top reviews in Middlebury

A multi-story hotel with a brick facade, large windows, and a parking lot.
Wyndham Southbury

Wyndham Southbury

Wyndham Southbury
Southbury

10/10 Excellent

We arrive late night and the process was easygoing. Well kept rooms, very comfy beds, plenty of towels and the sofa bed was a plus since we traveled 5 of us and my service dog. We all slept through the night! Will come back definitely if we are back in town.
Canada
Andrea
Reviewed July 20, 2026
Wyndham Southbury

Frequently Asked Questions

How much do cottages in Middlebury cost?

Prices for cottages in Middlebury range between CA $179 and CA $381 per night. Whatever your budget, you'll find a perfect place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your cottage in Middlebury with Expedia?

Expedia has some superb cottages in Middlebury, so start packing for an unforgettable stay on nature's doorstep. If you're sticking to a budget, choose how much you'd like to spend and the star rating of your property. Or, make the most of our filters to search for cottages with free WiFi or a pool. We'll help you find the perfect fit whatever your plans or bank balance.

How can I find cheap cottages in Middlebury?

Expedia can help you easily track down cheap cottages in Middlebury. To lock in your special stay in just a few keystrokes, simply use our handy filter tool to tailor your search results by star rating, amenities and budget.

What is there to do in Middlebury near my cottage?

After you've unpacked your bags, head out and explore the wonderful things Middlebury has on offer. Quassy Amusement Park is a top attraction to add to your must-do list.

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