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A rustic barn surrounded by autumn foliage and a field.

Windsor
Connecticut
United States of America
North America
Hotwire.com

Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Omni New Haven Hotel at Yale

4 out of 5

Price was $575, price is now $498 per person

$498

per person

Dec 20 - Dec 23

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shubert Theater and New Haven Green are located nearby.

Beechmont - Perfect for Family Retreat!

5 out of 5

Price was $2,273, price is now $1,269 per person

$1,269

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Svihra Park and Beardsley Zoo are located nearby.

Hyatus Luxury Residences City Crossing

4 out of 5

Price was $860, price is now $692 per person

$692

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

Book a stay at this business-friendly aparthotel in New Haven. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Knights of Columbus Museum and Shubert Theater are located nearby.

Bed had no mattress cover but was very comfortable. Only one working lamp. Vents could use a good cleaning. I would recommend it and would stay again.

Reviewed on Oct 25, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5

Price was $831, price is now $681 per person

$681

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

Stay at this aparthotel in New Haven. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Shubert Theater and White Space Gallery are located nearby.

We stayed for a week and had a great trip, apartment was clean and cozy and the bathroom was very big. When we come back we will consider staying here again

Reviewed on Oct 26, 2026

Landing Apartments New Haven Near Dixwell

3 out of 5

Price was $667, price is now $583 per person

$583

per person

Dec 20 - Dec 23

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

Stay at this apartment in New Haven. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Peabody Museum of Natural History and Grove Street Cemetery are located nearby.

The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Graduate by Hilton New Haven

4 out of 5

Price was $576, price is now $509 per person

$509

per person

Dec 20 - Dec 23

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

Stay at this hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and free bicycles on site. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Art Plus Studio and Harkness Tower are located nearby.

Mayflower Motel Milford

2 out of 5

Price was $669, price is now $593 per person

$593

per person

Dec 22 - Dec 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

Stay at this motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Bowlero Milford are located nearby.

Landing Furnished Apartment Near Yale University

3 out of 5

Price was $809, price is now $718 per person

$718

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

Stay at this apartment in New Haven. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Shubert Theater and White Space Gallery are located nearby.