Search Deals on
Old Saybrook Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

Summer sunset on the Connecticut River, Shoreline, and Long Island Sound in Old Saybrook, CT, with Lynde Lighthouse in the foreground, along with Fenwick, and a colorful summer sunset sky

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.

Pier Blue Inn Old Saybrook - Essex

2 out of 5

Price was $603, price is now $446 per person

$446

per person

Aug 28 - Aug 31

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.

New Haven Hotel

3.5 out of 5

Price was $607, price is now $469 per person

$469

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.

Landing Apartments New Haven Near Dixwell

3 out of 5

Price was $858, price is now $676 per person

$676

per person

Jul 16 - Jul 19

found 7 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 Payne Whitney Gymnasium and Peabody Museum of Natural History are located nearby.

Graduate by Hilton New Haven

4 out of 5

Price was $747, price is now $592 per person

$592

per person

Jul 16 - Jul 19

found 7 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Hyatus Luxury Residences City Crossing

4 out of 5

Save 100% on your flight

Price was $1,321, price is now $1,048 per person

$1,048

per person

Jul 16 - Jul 19

found 7 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 Shubert Theater and White Space Gallery are located nearby.

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5

Save 100% on your flight

Price was $1,512, price is now $1,200 per person

$1,200

per person

Jul 16 - Jul 19

found 7 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.

Omni New Haven Hotel at Yale

4 out of 5

Price was $554, price is now $449 per person

$449

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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

Save 100% on your flight

Price was $1,341, price is now $1,113 per person

$1,113

per person

Jul 14 - Jul 16

found 24 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 Hartford HealthCare Amphitheater and Svihra Park are located nearby.