Roxbury Vacations from $790
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Roxbury Vacation Packages
- Club Wyndham Smugglers’ Notch Vermont
Oct 15 - Oct 18Club Wyndham Smugglers’ Notch Vermont + Flight
Jeffersonville3 nights3.5 star property8.4/10 - Very Good (223 reviews)Roundtrip • Washington (IAD) - Burlington (BTV)IAD - BTV • Nonstop BTV - IAD • 1 stop$1,012$790found 1 day agoper traveler - The Essex Resort & Spa
Oct 7 - Oct 12The Essex Resort & Spa + Flight
Essex Junction5 nights4.0 star property9.0/10 - Wonderful (1,001 reviews)"The positives: The rooms and the property were immaculately clean and well-kept and the choice of pools (indoor and outdoor) was a nice amenity. The negatives: Booking through Expedia incurred a $10 fee that was unexpected and the hotel staff did a mediocre job explaining the rationale for that charge. Being a culinary resort, I expected more treats included for guests and if not free breakfast, then at least a meal subsidy at one of the onsite eateries. All in all, it’s a nice, quiet place..."Reviewed July 29, 2026Roundtrip • Washington (DCA) - Burlington (BTV)DCA - BTV • Nonstop BTV - DCA • Nonstop - Smugglers' Notch Resort Private Suites
Oct 7 - Oct 12Smugglers' Notch Resort Private Suites + Flight
Jeffersonville5 nights3.5 star property7.8/10 - Good (21 reviews)"DO NOT STAY HERE——What should have been a relaxing stay turned into an infuriating and exhausting ordeal due to gross negligence and unprofessional conduct by the property management company overseeing this privately owned condo. On my second day I left briefly for breakfast and after I returned I was shocked to discover that the door code to my condo did not work, leaving me locked out of the property. I called the property management office multiple times before anyone answered. When I..."Reviewed October 15, 2025Roundtrip • Washington (DCA) - Burlington (BTV)DCA - BTV • Nonstop BTV - DCA • Nonstop - West Hill House B&B
Oct 12 - Oct 15West Hill House B&B + Flight
Warren3 nights3.5 star property10/10 - Exceptional (11 reviews)Roundtrip • Chicago (ORD) - Burlington (BTV)ORD - BTV • Nonstop BTV - ORD • Nonstop$1,161$890found 12 hours agoper traveler - Outbound Stowe
Oct 7 - Oct 12Outbound Stowe + Flight
Stowe5 nights3.5 star property9.0/10 - Wonderful (372 reviews)Roundtrip • Washington (DCA) - Burlington (BTV)DCA - BTV • Nonstop BTV - DCA • Nonstop
Roxbury Hotel Deals
Comfort Inn & Suites Montpelier-Berlin
Comfort Inn & Suites Montpelier-Berlin
Frequently Asked Questions
How much does a Roxbury vacation package cost?
Offering excellent value package deals from $790 on Expedia, you'll be thrilled with how little a vacation to Roxbury costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Roxbury?
If you'd like to book a cheap Roxbury vacation package, consider visiting in April, May and December. You're likely to find better rates on hotels and flights during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Roxbury?
Generally, a handful of days is enough to tick off the major sights during your Roxbury vacation. But if you want to have some time to rest or go on day trips, consider extending your itinerary.
How to find the best Roxbury package deals?
Use Expedia's handy filters to help you find some unbeatable Roxbury package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Roxbury package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Roxbury vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still have the flexibility to create a customized Roxbury vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Roxbury?
If you're considering an impromptu Roxbury getaway, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find incredible deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Roxbury vacation packages?
Jet off on your perfect trip to Roxbury with help from our Book Now, Pay Later vacations. No need to scrimp and save or hold off until the next payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to budget for your trip and snap up travel deals before they disappear.