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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 $225, price is now $187 per person
$187
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) 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 Milford Plaza Shopping Center are located nearby.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Save 100% on your flight
Price was $344, price is now $239 per person
$239
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Milford Plaza Shopping Center are located nearby.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Save 100% on your flight
Price was $399, price is now $293 per person
$293
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star 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 White Space Gallery are located nearby.
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
Save 100% on your flight
Price was $564, price is now $418 per person
$418
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star aparthotel in New Haven. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Shubert Theater and White Space Gallery 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 $435, price is now $340 per person
$340
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shubert Theater and New Haven Green are located nearby.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $511, price is now $400 per person
$400
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Barnes Museum and Southington Public Library are located nearby.
Clarion Inn

Clarion Inn

3 out of 5
Price was $284, price is now $230 per person
$230
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quinnipiac River State Park and Wharton Brook State Park are located nearby.
The Blake Hotel

The Blake Hotel

4 out of 5
Save 100% on your flight
Price was $543, price is now $449 per person
$449
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.

Middlebury Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Save 100% on your flight
Price was $344, price is now $239 per person
$239
per person
Dec 11 - Dec 14
found 4 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
Save 100% on your flight
Price was $399, price is now $293 per person
$293
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $564, price is now $418 per person
$418
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $435, price is now $340 per person
$340
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Middlebury Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $824, price is now $656 per person
$656
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $845, price is now $658 per person
$658
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $958, price is now $791 per person
$791
per person
Dec 7 - Dec 14
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $955, price is now $810 per person
$810
per person
Dec 7 - Dec 14
found 3 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.

Breeze Airways
Wed, Nov 19 - Sun, Dec 7
SFO
San Francisco Intl.
HVN
Tweed - New Haven Regional
$626 Roundtrip, found 18 hours ago
$626
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Wed, Nov 19 from San Francisco Intl. to Tweed - New Haven Regional, returning Sun, Dec 7, priced at $626 found 18 hours ago
Breeze Airways
Wed, Nov 19 - Thu, Dec 4
SFO
San Francisco Intl.
HVN
Tweed - New Haven Regional
$635 Roundtrip, found 18 hours ago
$635
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Wed, Nov 19 from San Francisco Intl. to Tweed - New Haven Regional, returning Thu, Dec 4, priced at $635 found 18 hours ago
Breeze Airways
Wed, Nov 19 - Fri, Dec 5
SFO
San Francisco Intl.
HVN
Tweed - New Haven Regional
$638 Roundtrip, found 18 hours ago
$638
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Wed, Nov 19 from San Francisco Intl. to Tweed - New Haven Regional, returning Fri, Dec 5, priced at $638 found 18 hours ago
Breeze Airways
Wed, Nov 19 - Sun, Nov 23
SFO
San Francisco Intl.
HVN
Tweed - New Haven Regional
$692 Roundtrip, found 1 day ago
$692
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Nov 19 from San Francisco Intl. to Tweed - New Haven Regional, returning Sun, Nov 23, priced at $692 found 1 day ago