Roxbury Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Brokaw

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Roxbury Vacation Packages

Roxbury Hotel Deals

Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is ₩128,189 per night from Sep 7 to Sep 8
₩128,189
₩147,418 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"It was great"

Reviewed on Aug 21, 2025

Wyndham Southbury
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd, Shelton, CT
Fully refundableReserve now, pay when you stay
The price is ₩151,710 per night from Aug 31 to Sep 1
₩151,710
₩174,467 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Brief Stay
"Easy access and comfortable"

Reviewed on Aug 11, 2025

Hilton Garden Inn Shelton
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 ₩123,139 per night from Sep 2 to Sep 3
₩123,139
₩141,609 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"The location is convenient."

Reviewed on Aug 21, 2025

Courtyard by Marriott Waterbury Downtown
See all 657 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.