Search Deals onMiddlefield Vacation Packages
Middlefield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Best Western Executive Hotel Of New Haven - West Haven
Price was $540, price is now $474 per person
$474
per person
Nov 19 - Nov 22
found 16 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 Oak Street Beach are located nearby.
A Best Western Hotel living up to expectations with great service, nice lobby, clean and good-sized rooms, Breakfast had a good variety of selection, wifi was good, the location is great - right next to a lot of restaurant and shops. We only stayed one night but wish we stayed longer.
Reviewed on Oct 9, 2026
Beechmont - Perfect for Family Retreat!
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 4 hours 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.
Landing Apartments New Haven Near Dixwell
Price was $1,345, price is now $1,034 per person
$1,034
per person
Nov 25 - Nov 29
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
Price was $943, price is now $731 per person
$731
per person
Dec 17 - Dec 23
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.
Hyatus Luxury Residences City Crossing
Price was $1,193, price is now $935 per person
$935
per person
Dec 17 - Dec 23
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
The Surfside Hotel
Save 100% on your flight
Price was $646, price is now $553 per person
$553
per person
Nov 14 - Nov 18
found 12 hours 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
Price was $701, price is now $605 per person
$605
per person
Dec 24 - Dec 27
found 4 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 Harkness Tower and Schubert Performing Arts Center are located nearby.
Water's Edge Resort & Spa
Price was $589, price is now $511 per person
$511
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Tanger Outlets and Westbrook Town Beach are located nearby.
We had a fantastic stay here. It was beautiful, clean and the staff was excellent. We will be back.
Reviewed on Oct 8, 2026
Middlefield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Middlefield Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Dec 2 - Mon, Dec 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$162 Roundtrip, found 7 hours ago
$162
Roundtrip
found 7 hours ago
Fri, Nov 6 - Mon, Nov 16
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
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
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$197 Roundtrip, found 16 hours ago
$197
Roundtrip
found 16 hours ago
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