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Middlebury Vacation Packages

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Middlebury Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Mayflower Motel Milford

Mayflower Motel Milford

2 out of 5
Price was $552, price is now $463 per person
$463
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Bowlero Milford are located nearby.

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,120, price is now $1,168 per person
$1,168
per person
Dec 14 - Dec 17
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 Beardsley Zoo and Lafayette Park are located nearby.

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Price was $1,351, price is now $1,033 per person
$1,033
per person
Dec 22 - Dec 28
found 2 hours 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

Omni New Haven Hotel at Yale

4 out of 5
Price was $818, price is now $643 per person
$643
per person
Nov 26 - Dec 1
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 Schubert Performing Arts Center and Shubert Theater are located nearby.
Good

Reviewed on Oct 19, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Price was $1,145, price is now $934 per person
$934
per person
Dec 22 - Dec 28
found 2 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.

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
Price was $1,091, price is now $893 per person
$893
per person
Nov 26 - Dec 1
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.
Fast and effective check-in, great amenities in the building. Kitchen well furnished. Overall great experience.

Reviewed on Oct 11, 2026

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 $604, price is now $510 per person
$510
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
Price was $969, price is now $828 per person
$828
per person
Nov 26 - Dec 1
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 Schubert Performing Arts Center are located nearby.
The location and accommodations were perfect.

Reviewed on Oct 20, 2026

Middlebury Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Mayflower Motel Milford

Mayflower Motel Milford

2 out of 5
Price was $432, price is now $375 per person
$375
per person
Dec 11 - Dec 14
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 $2,120, price is now $1,168 per person
$1,168
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $541, price is now $455 per person
$455
per person
Dec 14 - Dec 17
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 $582, price is now $507 per person
$507
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)

Middlebury 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 $818, price is now $643 per person
$643
per person
Nov 26 - Dec 1
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 $7,807, price is now $5,327 per person
$5,327
per person
Dec 22 - Dec 28
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $1,351, price is now $1,033 per person
$1,033
per person
Dec 22 - Dec 28
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $1,145, price is now $934 per person
$934
per person
Dec 22 - Dec 28
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Top Flight Deals

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

Avelo Airlines
Fri, Dec 11 - Sun, Dec 13
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$148 Roundtrip, found 5 days ago
$148
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, Dec 11 from Myrtle Beach Intl. to Tweed - New Haven Regional, returning Sun, Dec 13, priced at $148 found 5 days ago
Avelo Airlines
Fri, Dec 11 - Sun, Dec 13
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$158 Roundtrip, found 1 hour ago
$158
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Fri, Dec 11 from Myrtle Beach Intl. to Tweed - New Haven Regional, returning Sun, Dec 13, priced at $158 found 1 hour ago
Breeze Airways
Fri, Nov 13 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$183 Roundtrip, found 5 hours ago
$183
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Nov 13 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Nov 15, priced at $183 found 5 hours ago
Avelo Airlines
Fri, Dec 4 - Sun, Dec 6
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Dec 4 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $222 found 1 day ago