Roxbury Vacations from $475
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The Latest Roxbury Vacation Packages
- Hilton Garden Inn Milford
Oct 1 - Oct 5Hilton Garden Inn Milford + Flight
Milford4 nights3.0 star property8.8/10 - Excellent (1,002 reviews)Roundtrip • Orlando (MCO) - New Haven (HVN)MCO - HVN • Nonstop HVN - MCO • 1 stop - Hyatus Luxury Residences City Crossing
Oct 1 - Oct 5Hyatus Luxury Residences City Crossing + Flight
The Hill4 nights4.0 star property9.2/10 - Wonderful (32 reviews)"the room and amenities are well maintained, clean and convenient, the customer service is awesome , answering requests fast and responsive."Reviewed July 5, 2026Roundtrip • Orlando (MCO) - New Haven (HVN)MCO - HVN • Nonstop HVN - MCO • 1 stop - Landing Apartments New Haven
Oct 1 - Oct 5Landing Apartments New Haven + Flight
West New Haven4 nights3.0 star property2.0/10 - (1 review)"Dirty condo, couldn't access and staff not helpful "Reviewed February 8, 2026Roundtrip • Orlando (MCO) - New Haven (HVN)MCO - HVN • Nonstop HVN - MCO • 1 stop - Luxury Furnished Apartments by Hyatus Downtown at Yale
Oct 1 - Oct 5Luxury Furnished Apartments by Hyatus Downtown at Yale + Flight
The Hill4 nights3.5 star property9.6/10 - Exceptional (85 reviews)"I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived. The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!"Reviewed July 6, 2026Roundtrip • Orlando (MCO) - New Haven (HVN)MCO - HVN • Nonstop HVN - MCO • 1 stop - Graduate by Hilton New Haven
Oct 1 - Oct 5Graduate by Hilton New Haven + Flight
Downtown New Haven4 nights4.0 star property9.2/10 - Wonderful (1,005 reviews)"I loved the location and the character of this property! Every person I encountered on the staff went above and beyond. I'm from the south so I appreciate the friendliness of these folks. I was greeted every time I came and went, which was a lot, and they truly seemed to care about my stay. The only negative I have is that they don't have a full-service restaurant on site. I stayed at the property for almost a week. It would have been nice to be able to eat in a night or two. Also, guests need..."Reviewed July 23, 2026Roundtrip • Orlando (MCO) - New Haven (HVN)MCO - HVN • Nonstop HVN - MCO • 1 stop
Roxbury Hotel Deals
Heritage Hotel, Golf & Conference Center
Heritage Hotel, Golf & Conference Center
Microtel Inn & Suites by Wyndham Bethel/Danbury
Microtel Inn & Suites by Wyndham Bethel/Danbury
La Quinta Inn & Suites by Wyndham Danbury
La Quinta Inn & Suites by Wyndham Danbury
Comfort Inn & Suites Danbury-Bethel
Comfort Inn & Suites Danbury-Bethel
Frequently Asked Questions
How much does a Roxbury vacation package cost?
You can snap up a vacation package to this popular destination from $475 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.