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Check prices for these dates

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Nov 20 - Nov 22
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Dec 11 - Dec 13
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Jan 8 - Jan 10

Our top choices for Middlebury villas

A two-story house with a front porch, a small garden, and a brick driveway.

1. Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.

Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.
West New Haven
10.0 out of 10, Exceptional, (17 reviews)
"We had a wonderful stay! The house was spotlessly clean, thoughtfully furnished, and equipped with everything we needed. It truly felt like a home away from home, making our time in New Haven comfortable and relaxing.The location was also very convenient for exploring the city and visiting Yale University. We would highly recommend this place to anyone planning a trip to New Haven, and we would happily stay here again!"
United States
Li H.
The price is CA $1,060
CA $1,861 total
includes taxes & fees
Nov 19 - Nov 20
Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Minutes from Yale and downtown.
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.

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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

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What is there to do near my villa in Middlebury?

After you've unpacked your things and settled in, head out and explore the cool things Middlebury has for you to experience. Quassy Amusement Park is a top attraction to add to your travel itinerary.

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