Roxbury, CT

Travel Guide

A waterfall cascading over rocks into a clear river surrounded by lush greenery and trees.
A stone structure in a forested area with autumn foliage.
A rural landscape with a road, a barn, and a field.
Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Roxbury CT
Book a stay at this family-friendly vacation home in Roxbury. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Glebe House Museum and ...
9.6/10 Exceptional! (57 reviews)
"An incredible spacious house on a LARGE, beautiful and secluded piece of property. Communication with the host was very easy, pleasent and helpful. Bathrooms were very clean and quite nice. All bedrooms were VERY comfortable and clean. Definitely a great house and property for family gatherings. ..."

Reviewed on Oct 5, 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
$107 nightly
The price is $123 total per night from Nov 15 to Nov 16
$123 total
Nov 15 - Nov 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Ethan Allen Hotel
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
$130 nightly
The price is $149 total per night from Nov 5 to Nov 6
$149 total
Nov 5 - Nov 6
Total with taxes and fees
Book a stay at this boutique hotel in Southbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Heritage Hotel, Golf & Conference Center
See all 722 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.
Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Roxbury CT
Book a stay at this family-friendly vacation home in Roxbury. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Glebe House Museum and ...
9.6/10 Exceptional! (57 reviews)
"An incredible spacious house on a LARGE, beautiful and secluded piece of property. Communication with the host was very easy, pleasent and helpful. Bathrooms were very clean and quite nice. All bedrooms were VERY comfortable and clean. Definitely a great house and property for family gatherings. ..."

Reviewed on Oct 5, 2026

Litchfield County Four Season Country Paradise
Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!

Brewster NY
Enjoy air conditioning. Popular attractions Stanley Lasker Richter Memorial Park and Richter Park Golf Course are located nearby.
10/10 Exceptional! (2 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"

Reviewed on Oct 12, 2026

Welcome to Sweet Abby Rose!
Private Annex/Former Artist Studio

Private Annex/Former Artist Studio

Washington CT
Stay at this vacation home in New Preston. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Mount Bushnell State Park and Lake Waramaug ...
10/10 Exceptional! (64 reviews)
"The larger bedroom is beautiful, exceptionally comfortable bed, and a calming view of trees through the window. Hosts were very responsive. The kitchenette is just large enough to prepare coffee or tea in the morning. Within close range of many excellent restaurants."

Reviewed on Oct 29, 2026

Private Annex/Former Artist Studio
See all 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

When is the best time to visit Roxbury?
The best time to visit Roxbury is from May through September, when the weather is generally warm and pleasant. For fewer crowds and better value, the quieter months of December through March are a good option, offering a different experience with cooler temperatures and potential for snow.
What cuisines can you find in Roxbury?
In Roxbury you can find Mediterranean cuisine, with dishes like hummus, falafel, gyros, and kebabs. Travelers can also enjoy North American favorites, classic European fare, Italian specialties such as pasta and pizza, fresh seafood, and African dishes.
Can I book a refundable hotel in Roxbury?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Roxbury by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Roxbury with Expedia?
Expedia makes it easier to plan your Roxbury trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Roxbury?
The best choice depends on your travel style. Hotels in Roxbury can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Roxbury trip on Expedia?
Once you've booked your Roxbury trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Roxbury trip?
Expedia offers customer support before, during, and after your Roxbury trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Roxbury?
If it's your first trip to Roxbury, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Roxbury hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Roxbury hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Roxbury

A waterfall in a forested area with autumn foliage.

Southbury

A calm river reflecting trees and houses, a bridge, and a park with benches.

New Milford

A park with a paved walkway, trees, and historic buildings in the background.

Woodbury

A river flowing through a forest with autumn foliage.

Washington

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