Roxbury Vacation Packages
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- Plan, book, travel with confidence
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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.
Landing Apartments New Haven Near Dixwell
Newhallville
CA $961
per person
Dec 11 - Dec 15
found 22 hours ago
Roundtrip flight included
Montreal (YUL) 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
Landing Furnished Apartment Near Yale University
Downtown New Haven
CA $802
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent
Reviewed on Sep 14, 2026
Graduate by Hilton New Haven
Downtown New Haven
CA $799
per person
Dec 11 - Dec 15
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.2/10 Wonderful! (1,001 reviews)
This place was wonderful! My friend and I had a bad experience at our previous hotel and stayed here for our last night in New Haven. The staff let us check-in 4 hours early and checkout late for free and were so kind and helpful. The room and amenities were decorated beautifully. Definitely would recommend for anyone staying in downtown!
Reviewed on Sep 20, 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 $164
CA $189 total
Sep 27 - Sep 28
includes taxes & fees
Hilton Garden Inn Shelton
25 Old Stratford Rd Shelton CT
Fully refundableReserve now, pay when you stay
CA $208
CA $239 total
Sep 28 - Sep 29
includes taxes & fees
Wyndham Southbury
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
CA $122
CA $140 total
Oct 19 - Oct 20
includes taxes & fees
8.2/10 Very good! (1,307 reviews)
"Sadly- this hotel has seen better days."
Reviewed on Sep 20, 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.
Frequently asked questions
How much does a Roxbury vacation package cost?
Offering great value package deals from CA $780 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.
