
Roxbury Vacations from $487
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Your Roxbury Vacation
From its rich history to its spectacular views and beyond, there's a whole lot to like about Roxbury. Uncover the wonders of this fascinating city with a Roxbury vacation package that's tailored to you. You'll want to take in some sights during your trip to Roxbury. Don't miss big-name attractions such as Glebe House Museum and The Gertrude Jekyll Garden, Woodbury Ski Area and Pilgrim Mall Shopping Center. Whatever your travel plans or budget, putting together a tailored Roxbury vacation is a cinch with Expedia.
The Latest Roxbury vacation packages
Price found within the past 48 hours. Click for updated prices.



Luxury Apartments by Hyatus at Pierpont
The Hill
Save 100% on your flight
Price was $1,405, price is now $1,035 per person
$1,035
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.
Reviewed on Jun 27, 2025

Graduate by Hilton New Haven
Downtown New Haven
Save 100% on your flight
Price was $1,170, price is now $867 per person
$867
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (861 reviews)
Loved everything except the bed. The mattress was old and uncomfortable
Reviewed on Aug 25, 2025

Omni New Haven Hotel at Yale
Downtown New Haven
Save 100% on your flight
Price was $1,385, price is now $1,047 per person
$1,047
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,008 reviews)
Very loud due to multiple bars and clubs right out side the hotel but that’s the only negative. It’s in a good location, with a lot to do around, which is why it’s loud in the area. Place is very nice and clean. Great security and easy to find parking.
Reviewed on Aug 24, 2025
Roxbury Hotel Deals

Litchfield County Four Season Country Paradise
Roxbury
9.4/10 Exceptional! (47 reviews)
Perfect for our family
"Beautiful property with wonderful amenities."
Reviewed on Aug 21, 2025

Wyndham Southbury
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Sep 7 to Sep 8
$107 total
Sep 7 - Sep 8
Total with taxes and fees
8/10 Very Good! (1,009 reviews)
"Great customer service!"
Reviewed on Aug 24, 2025

Hilton Garden Inn Shelton
25 Old Stratford Rd, Shelton, CT
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $139 total per night from Aug 31 to Sep 1
$139 total
Aug 31 - Sep 1
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"Good value for the money."
Reviewed on Aug 22, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.