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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
Price was $787, price is now $647 per person
$647
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Seabluff Beach and Bradley Point Beach are located nearby.
It was very clean and the staff was friendly

Reviewed on Aug 9, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,962, price is now $1,581 per person
$1,581
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
Save 100% on your flight
Price was $1,282, price is now $951 per person
$951
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!

Reviewed on Jul 24, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Save 100% on your flight
Price was $1,212, price is now $914 per person
$914
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
Save 100% on your flight
Price was $1,320, price is now $1,032 per person
$1,032
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 Schubert Performing Arts Center are located nearby.
I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived. The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!

Reviewed on Jul 6, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Save 100% on your flight
Price was $894, price is now $709 per person
$709
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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 Shubert Theater and Sterling Memorial Library at Yale University are located nearby.

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Save 100% on your flight
Price was $1,065, price is now $868 per person
$868
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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.

The Surfside Hotel

The Surfside Hotel

2 out of 5
Price was $825, price is now $679 per person
$679
per person
Oct 14 - Oct 18
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 Hartford HealthCare Amphitheater and Long Beach are located nearby.
Fitness room doesn’t have a basic trenageur with a cross bar. Housekeeping enter the room to do cleaning when not asked to

Reviewed on Aug 8, 2026

Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,212, price is now $914 per person
$914
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,962, price is now $1,581 per person
$1,581
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,282, price is now $951 per person
$951
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
Save 100% on your flight
Price was $1,320, price is now $1,032 per person
$1,032
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)

Windsor Vacation Packages 5-7 Night Stays

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 $578, price is now $494 per person
$494
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $1,267, price is now $966 per person
$966
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $1,391, price is now $1,102 per person
$1,102
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Head of Pond House

Head of Pond House

3 out of 5
Save 100% on your flight
Price was $1,530, price is now $1,263 per person
$1,263
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to New Haven (HVN)

Top Flight Deals

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

Frontier Airlines
Thu, Oct 22 - Sun, Oct 25
MCO
Orlando Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 13 hours ago
$108
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Orlando Intl. to Bradley Intl., returning Sun, Oct 25, priced at $108 found 13 hours ago
Breeze Airways
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $185 found 4 days ago
Frontier Airlines
Mon, Sep 28 - Fri, Oct 9
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Fri, Oct 9, priced at $203 found 1 day ago
Breeze Airways
Wed, Sep 2 - Tue, Sep 8
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$204 Roundtrip, found 4 days ago
$204
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Sep 8, priced at $204 found 4 days ago