Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Middlebury holiday rentals

A spacious living room with large windows, a fireplace, and a view of the outdoors.

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 S$689
includes taxes & fees
20 Nov - 21 Nov
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
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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Find holiday rentals that suit your style

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Top Middlebury Hotel Reviews

An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.
Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven
The Centre

8/10 Good

No bad
Singapore
Joo Wee
Reviewed June 10, 2025
Home2 Suites by Hilton East Haven New Haven

Frequently Asked Questions

Can I find holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Quassy Amusement Park, or you can select a more secluded option if you're looking for a relaxing stay. Middlebury is known for its parks.

What’s there to see and do in Middlebury?

Family-friendly attractions include Quassy Amusement Park, whereas Lake Quassapaug is a spot to enjoy the outdoors. In the wider area, you’ll find Palace Theatre and Beacon Falls Town Recreation Field.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.