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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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Price was $613, price is now $467 per person
$467
per person
Jul 10 - Jul 13
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,006, price is now $728 per person
$728
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 convenient parking in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.
Landing Furnished Apartments near YSM

Landing Furnished Apartments near YSM

3 out of 5
Save 100% on your flight
Price was $1,361, price is now $985 per person
$985
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy a fitness center, a business center, and satellite TV channels. Popular attractions Shubert Theater and White Space Gallery are located nearby.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Save 100% on your flight
Price was $836, price is now $618 per person
$618
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Payne Whitney Gymnasium and Peabody Museum of Natural History are located nearby.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Price was $960, price is now $715 per person
$715
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $3,816, price is now $2,913 per person
$2,913
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,548, price is now $1,186 per person
$1,186
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Shubert Theater and White Space Gallery are located nearby.
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 $1,579, price is now $1,218 per person
$1,218
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 White Space Gallery are located nearby.

Windsor 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 $517, price is now $397 per person
$397
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
Price was $551, price is now $401 per person
$401
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $836, price is now $618 per person
$618
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $613, price is now $467 per person
$467
per person
Jul 10 - Jul 13
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) to New Haven (HVN)

Windsor Vacation Packages 5-7 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 $960, price is now $715 per person
$715
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,006, price is now $728 per person
$728
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Landing Furnished Apartments near YSM

Landing Furnished Apartments near YSM

3 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,361, price is now $985 per person
$985
per person
Aug 25 - Aug 31
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 $3,816, price is now $2,913 per person
$2,913
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 6 days ago
$142
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $142 found 6 days ago
Frontier Airlines
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$146 Roundtrip, found 2 hours ago
$146
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $146 found 2 hours ago
Breeze Airways
Tue, Jul 21 - Tue, Jul 28
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$190 Roundtrip, found 4 hours ago
$190
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Tue, Jul 21 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Jul 28, priced at $190 found 4 hours ago
Bargain Flight
Wed, Jul 29 - Wed, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Jul 29 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Wed, Aug 19, priced at $229 found 1 day ago