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Cheshire Vacation Packages

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Cheshire Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Price was $425, price is now $329 per person
$329
per person
Sep 18 - Sep 21
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 breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Long Wharf Theatre and Knights of Columbus Museum are located nearby.
Upgraded!

Reviewed on Aug 7, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
Save 100% on your flight
Price was $900, price is now $648 per person
$648
per person
Sep 18 - Sep 21
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 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 $1,213, price is now $912 per person
$912
per person
Sep 21 - Sep 26
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

New Haven Hotel

New Haven Hotel

3.5 out of 5
Save 100% on your flight
Price was $854, price is now $655 per person
$655
per person
Sep 21 - Sep 26
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 New Haven Green are located nearby.
Nice clean room, very helpful and friendly staff, Everyone we interacted with was polite & helpful and engaged, from maintenance staff to front desk.,

Reviewed on Aug 7, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Save 100% on your flight
Price was $1,362, price is now $1,047 per person
$1,047
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

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 $1,616, price is now $1,246 per person
$1,246
per person
Oct 11 - Oct 17
found 24 hours 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 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

Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Price was $574, price is now $460 per person
$460
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this hotel in Milford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westfield Connecticut Post Mall and Milford Plaza Shopping Center are located nearby.

The Blake Hotel

The Blake Hotel

4 out of 5
Save 100% on your flight
Price was $1,049, price is now $854 per person
$854
per person
Sep 18 - Sep 21
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, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shubert Theater and New Haven Green are located nearby.
Nice hotel good staff and service!

Reviewed on Aug 7, 2026

Cheshire Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Long Wharf
Price was $425, price is now $329 per person
$329
per person
Sep 18 - Sep 21
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
Save 100% on your flight
Price was $1,034, price is now $739 per person
$739
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $900, price is now $648 per person
$648
per person
Sep 18 - Sep 21
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 $676, price is now $496 per person
$496
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)

Cheshire Vacation Packages 5-7 Night Stays

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

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
Price was $854, price is now $655 per person
$655
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
Save 100% on your flight
Price was $1,213, price is now $912 per person
$912
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,537, price is now $1,179 per person
$1,179
per person
Oct 11 - Oct 17
found 24 hours 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
Save 100% on your flight
Price was $1,362, price is now $1,047 per person
$1,047
per person
Sep 21 - Sep 26
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
Mon, Aug 31 - Mon, Sep 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Mon, Aug 31 from Orlando Intl. to Bradley Intl., returning Mon, Sep 14, priced at $132 found 2 hours ago
Breeze Airways
Wed, Aug 26 - Tue, Sep 1
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$137 Roundtrip, found 8 hours ago
$137
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Sep 1, priced at $137 found 8 hours ago
Avelo Airlines
Fri, Aug 28 - Sun, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Fri, Aug 28 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Aug 30, priced at $138 found 2 days ago
Breeze Airways
Wed, Sep 2 - Wed, Sep 9
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$183 Roundtrip, found 4 days ago
$183
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Wed, Sep 9, priced at $183 found 4 days ago