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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.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $277, price is now $233 per person
$233
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Seabluff Beach and Bradley Point Beach are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,094, price is now $1,141 per person
$1,141
per person
Mar 9 - Mar 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Glenwood Park and Beardsley Zoo are located nearby.

Landing Modern 2bd, Gym

3 out of 5
Price was $562, price is now $432 per person
$432
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy air conditioning. Popular attractions Judges Cave and Yale Bowl are located nearby.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Price was $488, price is now $382 per person
$382
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) 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 White Space Gallery are located nearby.
The Surfside Hotel

The Surfside Hotel

2 out of 5
Save 100% on your flight
Price was $689, price is now $574 per person
$574
per person
Mar 26 - Apr 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
Book a stay at this beach hotel in Stratford. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Long Beach and Lordship Beach are located nearby.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
Price was $366, price is now $306 per person
$306
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) 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 clean rooms in our reviews. Popular attractions Art Plus Studio and White Space Gallery are located nearby.
Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was $303, price is now $255 per person
$255
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this golf hotel in Stratford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Perry House and Stratford Historical Society Capt David Judson House are located nearby.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $313, price is now $264 per person
$264
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) 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.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $366, price is now $306 per person
$306
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,094, price is now $1,141 per person
$1,141
per person
Mar 9 - Mar 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Price was $562, price is now $432 per person
$432
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $488, price is now $382 per person
$382
per person
Feb 26 - Mar 1
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Chester Vacation Packages 5-7 Night Stays

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

The Surfside Hotel

2 out of 5
Lordship
Save 100% on your flight
Price was $689, price is now $574 per person
$574
per person
Mar 26 - Apr 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Sat, Jan 17 - Sun, Jan 25
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$996 Roundtrip, found 3 days ago
$996
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Jan 17 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Jan 25, priced at $996 found 3 days ago
Breeze Airways
Fri, Jan 16 - Sun, Jan 25
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$1,008 Roundtrip, found 3 days ago
$1,008
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jan 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Jan 25, priced at $1,008 found 3 days ago
Breeze Airways
Sat, Jan 17 - Thu, Jan 22
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$1,051 Roundtrip, found 3 days ago
$1,051
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Jan 17 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Jan 22, priced at $1,051 found 3 days ago
Breeze Airways
Fri, Jan 16 - Thu, Jan 22
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$1,062 Roundtrip, found 3 days ago
$1,062
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jan 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Jan 22, priced at $1,062 found 3 days ago