Roxbury Vacation Packages
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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.
Top Roxbury Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Cheshire Welcome Inn
CA $646
per person
Oct 10 - Oct 14
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.4/10 Very good! (860 reviews)
First and foremost, the room was exceptionally clean. Kudos to the housekeeping staff. The room wasn’t fancy, but pleasant and for the most part well maintained. Bed was comfortable however pillows were as hard as rocks. It would have been nice to have options. There were plenty of towels which appeared to be brand new. The room offered the use of a coffeemaker, refrigerator and microwave. Our tv remote didn’t work but we operated the television manually as it was most likely a matter of needing new batteries.
The seemingly only drawback was the three o’clock check in time. Arriving around 1:00 we acknowledged that we were early but would just like the key as we were attending a reunion and would be returning quite late. We didn’t need to enter a room at that time since they were being cleaned. The receptionist was initially reluctant to accommodate but eventually made a concession and gave us the keycard. There was also a computer problem at check-in, which caused a minor delay, but all in all would recommend the accommodations for the price.
Reviewed on Aug 15, 2026
Omni New Haven Hotel at Yale
Downtown New Haven
CA $1,030
per person
Oct 10 - Oct 14
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.6/10 Excellent! (1,072 reviews)
Very nice rooms very helpful staff. On site parking very reasonably priced. Great restaurant on 19th floor with spectacular views of Yale.
Reviewed on Aug 17, 2026
Ready to book your vacation to Roxbury?
Roxbury Hotel Deals
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
CA $135
CA $156 total
Aug 23 - Aug 24
includes taxes & fees
8/10 Very good! (1,405 reviews)
"The tub filled up while taking a shower. Offered water to drink in the lobby on Saturday, but not on Sunday. BBed was comfortable"
Reviewed on Aug 18, 2026
Hotel Zero Degrees Danbury
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
CA $254
CA $292 total
Sep 3 - Sep 4
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Room was clean, spacious, updated"
Reviewed on Aug 17, 2026
Courtyard by Marriott Waterbury Downtown
63 Grand St Waterbury CT
CA $123
CA $142 total
Aug 30 - Aug 31
includes taxes & 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.
Frequently asked questions
How much does a Roxbury vacation package cost?
Offering great value package deals from CA $646 on Expedia, you'll be surprised at how little a vacation to Roxbury costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Roxbury?
If you're looking to book a cheap Roxbury vacation package, consider planning a trip in January, February and March. You're likely to find lower prices on accommodations and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Roxbury?
The ideal duration of your Roxbury vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to hit all the major attractions and discover some hidden treasures along the way.
How to find the best Roxbury package deals?
Begin your search for a Roxbury package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Roxbury package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Roxbury adventure underway.
Is it cheaper to book a Roxbury vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Roxbury vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Roxbury?
If you have your Roxbury vacation dates locked in, book early to bag some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Roxbury?
- Choose when to get away: Check your schedule and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Roxbury.
- Plan your budget wisely: Besides the price of your stay, you'll need to factor in other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that may crop up during your trip to Roxbury.
- Work out your trip length: Think about how long you'd like to spend exploring Roxbury. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
- Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the ideal Roxbury vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
