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Old Saybrook Vacation Packages

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A coastal town with a lighthouse, houses, and a river.

Old Saybrook
Connecticut
United States of America
North America
Hotwire.com

Old Saybrook Flight + Hotel Packages

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

Hyatt Place Milford / New Haven

3 out of 5

Price was $553, price is now $489 per person

$489

per person

Dec 31 - Jan 3

found 8 hours ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Milford Plaza Shopping Center 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 8 hours 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 8 hours 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 8 hours 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

Omni New Haven Hotel at Yale

4 out of 5

Price was $757, price is now $640 per person

$640

per person

Dec 22 - Dec 26

found 1 day 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.

I had zero compliants. Happy with everything- location. Parking wasn’t overly expensive and unlimited in and outs with my room key. Clean and very comfy room. Free beverage voucher. Friendly staff. Definitely would stay here again!

Reviewed on Nov 2, 2026

Mayflower Motel Milford

2 out of 5

Price was $725, price is now $614 per person

$614

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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 Apartments New Haven Near Dixwell

3 out of 5

Price was $1,016, price is now $881 per person

$881

per person

Dec 31 - Jan 3

found 8 hours ago

Roundtrip flight included

Chicago (ORD) 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 $750, price is now $660 per person

$660

per person

Dec 22 - Dec 26

found 1 day 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.

Old Saybrook Vacation Packages 3-4 Night Stays

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

Omni New Haven Hotel at Yale

4 out of 5

Downtown New Haven

Price was $757, price is now $640 per person

$640

per person

Dec 22 - Dec 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)