Roxbury Vacations from $683
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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.
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
$945
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to New Haven (HVN)
9.6/10 Exceptional! (88 reviews)
Excellent value — a very thoughtfully decorated and well-maintained apartment, effective air conditioning, blackout curtains in every room — really helped the vacation to feel like a “treat”!
I did feel their app / web portal had “quite a lot” baked in it which could feel intimidating at first — vs. a “easy button” version at the top for simple functions like lock/unlock door — but would absolutely consider other Hyatus properties in the future!
Reviewed on Sep 18, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$929
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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
New Haven Hotel
Downtown New Haven
$752
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to New Haven (HVN)
9.2/10 Wonderful! (2,294 reviews)
The room was clean and the hotel staff was OK. Parking is extra and located across the street. The downtown area that it situated down is nice and has some amenities. I wouldn’t stay here for a vacation but for a business trip it’s OK and serve the purpose Nicely as a business traveler looks for 9+ properties. This one fits at a nine.
Reviewed on Sep 23, 2026
Roxbury Hotel Deals
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
$110 nightly
$127 total
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Shelton
25 Old Stratford Rd Shelton CT
Fully refundableReserve now, pay when you stay
$149 nightly
$171 total
Oct 1 - Oct 2
Total with taxes and fees
8/10 Very Good! (1,099 reviews)
"Smelled clean, clean rooms and property, nice staff."
Reviewed on Sep 23, 2026
Wyndham Southbury
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
$87 nightly
$100 total
Oct 25 - Oct 26
Total with taxes and fees
8.2/10 Very Good! (1,308 reviews)
"Extra for microwave in room so if you want one be sure to book with it."
Reviewed on Sep 23, 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
How much does a Roxbury vacation package cost?
You can snap up a vacation package to this popular destination from $683 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?
If you'd like to score a cheap Roxbury vacation package, consider traveling in November, December and January. You'll generally find better prices on accommodations and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Roxbury?
With a well-organized schedule, you can easily hit the main Roxbury attractions in a handful of days. But if you'd like to explore off the beaten track or take day trips, think about 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.
Does Expedia offer Book Now, Pay Later Roxbury vacation packages?
Your Roxbury break should be a relaxing escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
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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.
