Middlebury, CT

Travel Guide

Photo by Brandon Miller
Photo by Brandon Miller

Where to stay in Middlebury

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Middlebury Center Historic District

Visitors to Middlebury Center Historic District enjoy its historic sites, and if you want to do some exploring, Lake Quassapaug is worth a stop.

Middlebury Center Historic District
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
The price is AED 591 per night from Oct 8 to Oct 9
AED 591
AED 680 total
8 Oct - 9 Oct
includes taxes & fees
Stay at this hotel in Trumbull. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,011 reviews)
"The room was spacious and the bed was comfortable. I needed to be near St. Vincent’s Hospital and the hotel location was convenient. It’s a little run down here and there but it’s still clean and comfortable. I’d stay here again."

Reviewed on 14 September 2025

Trumbull Marriott Shelton
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
The price is AED 585 per night from Oct 12 to Oct 13
AED 585
AED 672 total
12 Oct - 13 Oct
includes taxes & fees
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,007 reviews)
"Caring Staff + Great Location = Happy Yale Parents We had a great four-night stay while moving our daughter into Yale. The managers truly went above and beyond. At check-in, one manager patiently showed us alternative room options when we were worried about noise, and the room we chose was perfect. ..."

Reviewed on 18 September 2025

Omni New Haven Hotel at Yale
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
The price is AED 543 per night from Oct 5 to Oct 6
AED 543
AED 625 total
5 Oct - 6 Oct
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
9/10 Wonderful! (1,784 reviews)
"This is so close to the concert we were going too!! Felt very safe walking at night."

Reviewed on 21 September 2025

New Haven Hotel
See all 973 properties in Middlebury
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.
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
240 Congress Avenue, New Haven, CT
Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Shubert Theater and White Space Gallery are located nearby.
9.4/10 Exceptional! (54 reviews)
"Loved the property and we will surely be coming back."

Reviewed on 20 August 2025

Luxury Furnished Apartments by Hyatus Downtown at Yale
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

New Haven
Stay at this apartment in New Haven. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions John Slade Ely House and Peabody Museum ...
9/10 Wonderful! (4 reviews)
Perfect Spot!
"Great studio, worked well for our stay to attend Yale Commencement. The location is convenient to campus with multiple close dining options. Well appointed space with everything necessary for a comfortable stay. There are shared laundry and kitchen areas….be mindful of that if you’re planning to ..."

Reviewed on 1 June 2025

Charming Studio| Near Yale| Downtown New Haven
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield
Book a stay at this family-friendly vacation home in New Fairfield. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Squantz Pond State ...
9.2/10 Wonderful! (29 reviews)
"The property was beautiful, clean, and had everything you could possibly need and more. It was close to restaurants, breweries, and coffee shops. There was also plenty of hiking trails nearby. Katherine answered all of my questions quickly."

Reviewed on 13 September 2025

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
See all properties in Middlebury
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.

Popular places to visit

Quassy Amusement Park

Bring the kiddos to Quassy Amusement Park and have a fun-filled day at this theme park in Middlebury. Attend a sporting event in this family-friendly area.

Quassy Amusement Park