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Weatogue Vacation Packages

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Weatogue Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Price was $321, price is now $281 per person
$281
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,096, price is now $1,199 per person
$1,199
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Beardsley Zoo and Lafayette Park are located nearby.

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
Price was $977, price is now $802 per person
$802
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.

Reviewed on Aug 10, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Price was $853, price is now $705 per person
$705
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Price was $643, price is now $543 per person
$543
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Schubert Performing Arts Center and Shubert Theater are located nearby.

Mayflower Motel Milford

Mayflower Motel Milford

2 out of 5
Price was $695, price is now $587 per person
$587
per person
Dec 17 - Dec 23
found 12 hours 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.

The Surfside Hotel

The Surfside Hotel

2 out of 5
Save 100% on your flight
Price was $646, price is now $553 per person
$553
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Beautiful ocean front location. Private Sandy Beach. Clean and well maintained. Great onsite pub and restaurant. We enjoyed our stay so much!

Reviewed on Sep 16, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Price was $701, price is now $605 per person
$605
per person
Dec 24 - Dec 27
found 1 day 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 Harkness Tower and Schubert Performing Arts Center are located nearby.

Weatogue Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $643, price is now $543 per person
$543
per person
Dec 24 - Dec 27
found 1 day 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 $2,096, price is now $1,199 per person
$1,199
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $977, price is now $802 per person
$802
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $853, price is now $705 per person
$705
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Weatogue Vacation Packages 5-7 Night Stays

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

Mayflower Motel Milford

2 out of 5
Price was $695, price is now $587 per person
$587
per person
Dec 17 - Dec 23
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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 $741, price is now $638 per person
$638
per person
Dec 17 - Dec 23
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 $1,042, price is now $909 per person
$909
per person
Dec 17 - Dec 23
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $815, price is now $730 per person
$730
per person
Dec 17 - Dec 23
found 12 hours ago
Roundtrip flight included
Orlando (MCO) 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
Wed, Dec 2 - Mon, Dec 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$166 Roundtrip, found 2 hours ago
$166
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Dec 2 from Orlando Intl. to Bradley Intl., returning Mon, Dec 14, priced at $166 found 2 hours ago
Frontier Airlines
Fri, Nov 6 - Mon, Nov 16
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 6 from Luis Munoz Marin Intl. to Bradley Intl., returning Mon, Nov 16, priced at $177 found 1 day ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$182 Roundtrip, found 2 hours ago
$182
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $182 found 2 hours ago
Breeze Airways
Wed, Jan 27 - Tue, Feb 2
TPA
Tampa Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 9 hours ago
$197
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Jan 27 from Tampa Intl. to Bradley Intl., returning Tue, Feb 2, priced at $197 found 9 hours ago