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South Windsor Vacation Packages

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South Windsor Flight + Hotel Packages

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

New Haven Hotel

3.5 out of 5
Price was $671, price is now $564 per person
$564
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Convenient

Reviewed on Jul 4, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $1,355, price is now $951 per person
$951
per person
Sep 16 - Sep 19
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 Glenwood Park are located nearby.

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Save 100% on your flight
Price was $795, price is now $598 per person
$598
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
While the staff were very friendly and helpful. The property itself was like strolling back into 1980. It was not at all what I was expecting to find upon my arrival. Things were clean enough, but very outdated. I will say that the bed was actually very comfortable. The impression I gathered from the website was that of abotuque bed and breakfast, which was not at all the case.

Reviewed on Jul 3, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Price was $813, price is now $645 per person
$645
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
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

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
Price was $782, price is now $630 per person
$630
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip non-stop 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.
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 2026

Landing Furnished Apartments near YSM

Landing Furnished Apartments near YSM

3 out of 5
Price was $697, price is now $566 per person
$566
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 Schubert Performing Arts Center are located nearby.

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
Price was $1,250, price is now $1,033 per person
$1,033
per person
Aug 21 - Aug 24
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 Knights of Columbus Museum are located nearby.
Amazing rental. It was perfect!

Reviewed on Jun 20, 2026

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

5 out of 5
Price was $2,480, price is now $2,083 per person
$2,083
per person
Aug 4 - Aug 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New Haven (HVN)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Steep Rock Preserve and Institute for American Indian Studies Museum and Research Center are located nearby.

South Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartments near YSM

Landing Furnished Apartments near YSM

3 out of 5
Downtown New Haven
Price was $697, price is now $566 per person
$566
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,355, price is now $951 per person
$951
per person
Sep 16 - Sep 19
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 $813, price is now $645 per person
$645
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $1,205, price is now $991 per person
$991
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)

South Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was $561, price is now $479 per person
$479
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Save 100% on your flight
Price was $795, price is now $598 per person
$598
per person
Aug 11 - Aug 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 $2,209, price is now $1,812 per person
$1,812
per person
Aug 11 - Aug 16
found 5 hours ago
Roundtrip flight included
Miami (MIA) 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.
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $162 just found
Frontier Airlines
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$167 Roundtrip, found 6 hours ago
$167
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $167 found 6 hours ago
American Airlines
Mon, Aug 10 - Tue, Aug 25
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Aug 10 from Ronald Reagan Washington National to Bradley Intl., returning Tue, Aug 25, priced at $183 found 2 days ago
American Airlines
Tue, Aug 4 - Mon, Aug 10
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 4 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Aug 10, priced at $207 found 1 day ago