Roxbury Holidays

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Your Roxbury Holiday

With one of our holiday packages to Roxbury, you'll discover endless opportunities for relaxation and adventure. There's plenty to experience, including its rich history and spectacular views. A trip to Roxbury is a terrific opportunity to sightsee. Make sure you visit popular attractions like Lovers Leap State Park, Pilgrim Mall Shopping Centre and Woodbury Ski Area. Expedia has what you need to escape your routine. Tailor your holiday to Roxbury to suit your travel style, whatever that may be.

Roxbury Holiday

Roxbury Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Lake Waramaug State Park, Lovers Leap State Park and Woodbury Ski Area

Our pick of the best Roxbury Hotel Deals

Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Roxbury CT
9.4/10 Exceptional! (52 reviews)
"Great spot. Have stayed here 2x. Once w college friends reunion. Once w fam reunion. Perfect for both."

Reviewed on 3 July 2026

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Litchfield County Four Season Country Paradise
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 19 July to 20 July
AU$182
19 July - 20 July
includes taxes & fees
8/10 Very good! (1,300 reviews)
"This really isn't a fancy hotel but it is very quaint and quite nice to stay."

Reviewed on 10 July 2026

Ethan Allen Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is AU$144 per night from 2 Aug to 3 Aug
AU$144
2 Aug - 3 Aug
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"Never in my life that I experienced such horrible customer service. There was a male concierge with a ponytail who did not allow my friends to check in. One of them had their ID, but they weren’t allowed to check in because I wasn’t present. I explained to the concierge over the phone that my father ..."

Reviewed on 8 July 2026

Best Western Danbury/Bethel
See all 706 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Roxbury holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. But how much your holiday 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 holiday packages and you could score some great off-season deals.
How many days is enough for Roxbury?
With a well-organised 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 holiday 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 holiday package well in advance.
Is it cheaper to book a Roxbury holiday as a package?
An Expedia holiday package could land you great savings when compared to booking accommodation and flights separately. Better still, you can personalise 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 holiday 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 favourite 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 accommodation and airfare: After you've settled on your dates and duration, lock in the right Roxbury holiday package for you.

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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.