Roxbury Trips (flight + hotel)

Photo by Jennifer Brokaw

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to P 3,118 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Roxbury

Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
Fully refundableReserve now, pay when you stay
The price is P5,034 per night from Jun 30 to Jul 1
P5,034
P5,789 total
Jun 30 - Jul 1
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
Close to Interstate
"Pro's: Easy off and on to interstate, staff very friendly, two dining options inside, clean. Con's: Very noisy with traffic noise and sirens, even with us being on the 9th floor. Hotel is next to a hospital. Public parking deck is not free and did not appear to be monitored. No other parking option ..."

Reviewed on Jun 26, 2025

Courtyard by Marriott Waterbury Downtown
Wyndham Southbury
Wyndham Southbury
3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is P5,240 per night from Jul 6 to Jul 7
P5,240
P6,026 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very Good! (1,012 reviews)
"Our stay was for our grandson’s Bar Mitzvah And the room was comfortable and quiet. We hosted a wonderful brunch the following morning and it was delicious. Dorie, the catering manager, was spectacular. A great stay!"

Reviewed on Jun 28, 2025

Wyndham Southbury
Hotel Zero Degrees Danbury
Hotel Zero Degrees Danbury
4 out of 5
15 Milestone Road, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is P8,484 per night from Jul 3 to Jul 4
P8,484
P9,756 total
Jul 3 - Jul 4
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Great staff and very comfortable surroundings!"

Reviewed on Jun 25, 2025

Hotel Zero Degrees Danbury
See all 652 properties in Roxbury
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.

Frequently asked questions

How much does a Roxbury vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. But how much your vacation to Roxbury costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Roxbury?
You can usually find lower prices and better availability in January, February and March. Browse our cheap Roxbury vacation packages and you could score some great off-season deals.
How many days is enough for Roxbury?
With a well-organized travel plan, you can easily hit the main Roxbury sights in a handful of days. But if you prefer to discover hidden spots or go on day trips, consider booking your Roxbury vacation for longer.
How to find the best Roxbury package deals?
Use Expedia's filter tool to help you find some great Roxbury package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Roxbury package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Roxbury vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can personalize your Roxbury getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Roxbury?
Land fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Roxbury getaway.
How to plan a trip to Roxbury?

  1. Choose when to go: Check your calendar and get your bags packed. Your favorite season and the activities available will also help you decide when to escape to Roxbury.
  2. Plan your budget wisely: On top of the price of your hotel, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that could arise during your trip to Roxbury.
  3. Work out your trip length: Think about how long you'd like to spend exploring Roxbury. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your accommodations and airfare: After you've settled on your dates and duration, lock in the right Roxbury vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.