Roxbury Vacations from $593
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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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
$593
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8/10 Very Good! (1,003 reviews)
Staff was helpful and professional. Room was clean, basic, nice. The TV was a little sketchy-some stations were static. The bathroom shower was great: good flow, hot and soothing. Overall, very good for the price.
Reviewed on Sep 17, 2026
Water's Edge Resort & Spa
Westbrook Center
$846
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return.
Reviewed on Sep 15, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$873
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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
Hyatus Luxury Residences City Crossing
The Hill
$1,046
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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
New Haven Hotel
Downtown New Haven
$661
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.2/10 Wonderful! (2,294 reviews)
Clean room, friendly staff, convenient to Yale University campus… Local restaurants offered a wide variety of options.
Reviewed on Sep 17, 2026
Roxbury Hotel Deals
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
$107 nightly
$123 total
Sep 20 - Sep 21
Total with taxes and fees
8/10 Very Good! (1,444 reviews)
"The room was very clean and housekeeping was very respectful or our need for privacy. The front desk help was friendly and helpful. The rooms are a little dated and could use an update but were clean and comfortable. We had an excellent rate so we were very pleased with out stay."
Reviewed on Sep 17, 2026
Hilton Garden Inn Shelton
25 Old Stratford Rd Shelton CT
Fully refundableReserve now, pay when you stay
$149 nightly
$171 total
Sep 28 - Sep 29
Total with taxes and fees
8/10 Very Good! (1,099 reviews)
"Everything was great here. We only stayed one night but it was clean and in a safe area."
Reviewed on Sep 16, 2026
Wyndham Southbury
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
$87 nightly
$100 total
Oct 18 - Oct 19
Total with taxes and fees
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 $593 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.
