
Roxbury Vacations from $370
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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.



HYATT house Hartford North/Windsor
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
9/10 Wonderful! (1,004 reviews)
Very easy navigation to the hotel. Got exactly the room that I reserved, and even a little bit better. The hotel staff from front desk agent to assistant general manager to bartender to the breakfast hostess Were all incredibly friendly and warm and responsive. It felt like staying at a friend's place. Their last act upon our checkout was reflective of the service throughout our Multi-day stay: I asked if the breakfast coffee was still out and the front desk agent told me it was not but then offered to get me a cup of coffee from the kitchen, which she did right away and with a smile. It was so nice and such a kind gesture to this weary traveler, and it's the little things like that that make this a great place to stay.
Reviewed on Jul 10, 2025


Residence Inn by Marriott Southington
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (548 reviews)
Overall, a great experience. Staff were professional and addressed every question. This Residence Inn allows pets, which was key.
Reviewed on Jun 14, 2025
Roxbury Hotel Deals

Litchfield County Four Season Country Paradise
Roxbury
9.4/10 Exceptional! (40 reviews)
Great place
"As advertised, easy place to hang with friends."
Reviewed on Jul 6, 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 Jul 27 to Jul 28
$107 total
Jul 27 - Jul 28
Total includes taxes and fees
8/10 Very Good! (1,010 reviews)
"The staff there was very helpful. The cleaning staff was excellent also. The rooms were beautiful. We loved the pool. Thank you to everyone."
Reviewed on Jul 10, 2025

Hilton Garden Inn Shelton
25 Old Stratford Rd, Shelton, CT
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $127 total per night from Jul 20 to Jul 21
$127 total
Jul 20 - Jul 21
Total includes taxes and fees
7.8/10 Good! (1,003 reviews)
"Great stay"
Reviewed on Jul 11, 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.
Find the Best Roxbury Vacation Packages
Roxbury Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Lake Waramaug State Park, Lovers Leap State Park and Woodbury Ski Area |
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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.