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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $499, price is now $384 per person
$384
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Panthorn Park and Cheshire Hollow Farm are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $1,640, price is now $1,057 per person
$1,057
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
Stay at this 5-star luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Svihra Park and Glenwood Park are located nearby.
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
Price was $1,027, price is now $813 per person
$813
per person
Nov 26 - Nov 29
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Shubert Theater and White Space Gallery are located nearby.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $595, price is now $475 per person
$475
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windsor Arts Center and Northwest Park are located nearby.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Price was $1,354, price is now $1,085 per person
$1,085
per person
Nov 20 - Nov 24
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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 the convenient parking in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $528, price is now $425 per person
$425
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Barnes Museum and Southington Public Library are located nearby.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $482, price is now $392 per person
$392
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Crystal Bees and Hawks Landing Country Club are located nearby.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $775, price is now $642 per person
$642
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star 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.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $499, price is now $384 per person
$384
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $1,640, price is now $1,057 per person
$1,057
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $642, price is now $494 per person
$494
per person
Nov 26 - Nov 30
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was $1,027, price is now $813 per person
$813
per person
Nov 26 - Nov 29
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)

Chester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $673, price is now $486 per person
$486
per person
Dec 23 - Dec 30
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $712, price is now $527 per person
$527
per person
Dec 23 - Dec 30
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $852, price is now $648 per person
$648
per person
Dec 23 - Dec 30
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Days Inn by Wyndham Ridgefield

Days Inn by Wyndham Ridgefield

2 out of 5
Price was $691, price is now $545 per person
$545
per person
Nov 24 - Dec 1
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)