Roxbury Vacations from $839
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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.
Head of Pond House
$1,115
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
10/10 Exceptional! (16 reviews)
The cottage is quaint and old, it is showing its age. The beds were ever comfortable. The entertainment option was not a TV but a projector with a shoddy speaker. The spiral staircase to the upper level was treacherous to come down and several of the vertical supports were look making the decent and ascent scary. The pond side location was very nice and the little patio was special apart from the chainsaws from the unfortunately scheduled tree cutting by neighbors.
Reviewed on Sep 23, 2026
Hyatus Luxury Residences City Crossing
The Hill
$935
per person
Dec 17 - Dec 23
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 10, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$1,031
per person
Dec 22 - Dec 27
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
Roxbury Hotel Deals
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
$103 nightly
$118 total
Oct 25 - Oct 26
Total with taxes and fees
Best Western Danbury/Bethel
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
$100 nightly
$115 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Waterbury Downtown
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
$99 nightly
$114 total
Oct 25 - Oct 26
Total with taxes and fees
8.6/10 Excellent! (1,288 reviews)
"Location is ok ,the only problem was a weed smell outside of hotel and hallways"
Reviewed on Oct 6, 2026
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.
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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.
