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Roxbury Vacation Packages

Build your package with 2 more options

Roxbury 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 $321, price is now $281 per person
$281
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,096, price is now $1,199 per person
$1,199
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
Price was $977, price is now $802 per person
$802
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.

Reviewed on Aug 10, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Price was $853, price is now $705 per person
$705
per person
Dec 24 - Dec 27
found 1 day 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 $643, price is now $543 per person
$543
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Mayflower Motel Milford

Mayflower Motel Milford

2 out of 5
Price was $695, price is now $587 per person
$587
per person
Dec 17 - Dec 23
found 10 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 Bowlero Milford are located nearby.

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Price was $701, price is now $605 per person
$605
per person
Dec 24 - Dec 27
found 1 day 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.

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 $540, price is now $474 per person
$474
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Friendly check in . Dunkin' donuts right in front .

Reviewed on Oct 10, 2026

Roxbury 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 $643, price is now $543 per person
$543
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 $2,096, price is now $1,199 per person
$1,199
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $977, price is now $802 per person
$802
per person
Dec 24 - Dec 27
found 1 day 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 $853, price is now $705 per person
$705
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Roxbury Vacation Packages 5-7 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 $695, price is now $587 per person
$587
per person
Dec 17 - Dec 23
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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 $741, price is now $638 per person
$638
per person
Dec 17 - Dec 23
found 10 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 $1,042, price is now $909 per person
$909
per person
Dec 17 - Dec 23
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $815, price is now $730 per person
$730
per person
Dec 17 - Dec 23
found 10 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 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
Breeze Airways
Fri, Dec 25 - Thu, Dec 31
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Dec 25 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Dec 31, priced at $225 found 4 days ago
Breeze Airways
Fri, Dec 25 - Thu, Dec 31
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Dec 25 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Dec 31, priced at $230 found 4 days ago
Avelo Airlines
Fri, Nov 6 - Sun, Nov 8
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Nov 6 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Nov 8, priced at $233 found 1 day ago