Roxbury Vacations from $534

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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.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $696, price is now $534 per person
$534
per person
Jan 15 - Jan 18
found 16 hours ago
Roundtrip flight included
Houston (HOU) to New Haven (HVN)
9.2/10 Wonderful! (35 reviews)
Clean, spacious, cozy room. Would definitely book again.

Reviewed on Nov 12, 2026

Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $879, price is now $588 per person
$588
per person
Jan 15 - Jan 18
found 20 hours ago
Roundtrip non-stop flight included
Houston (HOU) to New Haven (HVN)
10/10 Exceptional! (1 review)

Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
Westbrook Center
Price was $827, price is now $630 per person
$630
per person
Jan 15 - Jan 18
found 16 hours ago
Roundtrip flight included
Houston (HOU) to New Haven (HVN)
9.8/10 Exceptional! (205 reviews)

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was $712, price is now $550 per person
$550
per person
Jan 15 - Jan 18
found 16 hours ago
Roundtrip flight included
Houston (HOU) to New Haven (HVN)
8.8/10 Excellent! (1,000 reviews)
Great location. The restaurant / bistro is very good. Try the salmon. Staff accommodating and helpful. Room and facilities were clean and inviting. Would stay again.

Reviewed on Nov 9, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was $715, price is now $556 per person
$556
per person
Jan 14 - Jan 17
found 20 hours ago
Roundtrip flight included
Houston (HOU) to New Haven (HVN)
9.6/10 Exceptional! (91 reviews)
There was a bit of a problem at first. The code did not work when we attempted to gain entry as instructed. It was sorted within about 30 minutes but it was a little unsettling as there is no one onsite to communicate with. In any event, everything after that was great. A clean, spacious, stylish, furnished apartment.

Reviewed on Nov 11, 2026

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Roxbury Hotel Deals

Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Roxbury CT
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
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Nov 29 to Nov 30
$116 total
Nov 29 - Nov 30
Total with taxes and fees
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
$97 nightly
The price is $111 total per night from Nov 29 to Nov 30
$111 total
Nov 29 - Nov 30
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
"Unfortunately the appointment of the room did not match the price. The room had not been well cleaned, the heat/air unit was too loud to have in operation. The fixtures were sub standard and did not match. The Continental breakfast could have been good but it wasn't hot enough and the potatoes were ..."

Reviewed on Nov 12, 2026

Best Western Danbury/Bethel
See all 713 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.

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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Frequently asked questions

What are the top things to do in Roxbury?
A Roxbury vacation offers a variety of outdoor activities and scenic views, making it ideal for nature lovers and romantic getaways. Here are some top attractions:

Browse and book things to do in Roxbury on Expedia.
How can I save money on a Roxbury vacation package?
When you bundle, you can save up to 30%*. To save money on a Roxbury package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Do you need to rent a car in Roxbury, or is public transport enough?
For a Roxbury vacation package, renting a car is highly recommended for exploring the area. Roxbury is an outdoor and nature destination outside a major city, with attractions spread out across the region. Major routes like Connecticut Route 67, Route 199, and Route 317 serve the town.

Having a car provides the flexibility to visit various lakes, vineyards, and conservation centers at your own pace. You'll also need a car to reach Roxbury from major airports such as New York, NY (JFK-John F. Kennedy Intl.), Newark Liberty Intl. Airport (EWR), New York, NY (LGA-LaGuardia), Hartford, CT (BDL-Bradley Intl.), or Albany, NY (ALB-Albany Intl.).
Can I change or cancel my Roxbury vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Roxbury vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Roxbury vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Roxbury vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Roxbury?
To find last-minute vacation packages to Roxbury, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Roxbury vacation packages?
Free cancellation on a Roxbury vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Roxbury vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Roxbury getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Roxbury vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

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