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.
Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was CA $890, price is now CA $888 per person
CA $888
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.2/10 Very good! (1,000 reviews)
It was convenient to town and shopping. Our air conditioner leaked all over the rug and it was soaking wet. Pillows were awful. We would not stay there again.

Reviewed on Nov 6, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,182, price is now CA $1,916 per person
CA $1,916
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New Haven (HVN)
No reviews

The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was CA $1,262, price is now CA $1,118 per person
CA $1,118
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (227 reviews)

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Roxbury Hotel Deals

Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Roxbury CT
9.6/10 Exceptional! (57 reviews)
"An incredible spacious house on a LARGE, beautiful and secluded piece of property. Communication with the host was very easy, pleasent and helpful. Bathrooms were very clean and quite nice. All bedrooms were VERY comfortable and clean. Definitely a great house and property for family gatherings. ..."

Reviewed on Oct 5, 2026

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Litchfield County Four Season Country Paradise
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Dec 6 to Dec 7
CA $142
CA $164 total
Dec 6 - Dec 7
includes taxes & fees
8/10 Very good! (1,553 reviews)
"Insane line to check in. There was one person working and we waited 47 minutes to check into our room. How do you only have 1 person working on a Saturday handling check ins. Ridiculous."

Reviewed on Nov 10, 2026

Ethan Allen Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Nov 30 to Dec 1
CA $137
CA $157 total
Nov 30 - Dec 1
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"Clean place. Good location. Convenient shopping."

Reviewed on Nov 10, 2026

Best Western Danbury/Bethel
See all 713 properties in Roxbury
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.
All Inclusive Vacations
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Beach Vacations
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Frequently asked questions

How much does a Roxbury vacation package cost?
Offering great value package deals from CA $888 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.