Roxbury Vacations from $228

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The Latest Roxbury vacation packages

Price found within the past 48 hours. Click for updated prices.
The Hidden Inn

The Hidden Inn

4 out of 5
Save 100% on your flight
Price was $301, price is now $228 per person
$228
per person
Feb 6 - Feb 8
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)
8.8/10 Excellent! (54 reviews)
Perfect accommodations when visiting relatives in the area.

Reviewed on Nov 30, 2025

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $762, price is now $644 per person
$644
per person
Feb 6 - Feb 8
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
8.6/10 Excellent! (17 reviews)
Hot tub could have been cleaner but all in all. Beautiful and amazing views! Great service with the front desk calls and extra towels provided no problem!

Reviewed on Sep 15, 2025

Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $539, price is now $462 per person
$462
per person
Feb 6 - Feb 8
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
9.4/10 Exceptional! (699 reviews)
Room was clean and staff were excellent, especially Holly; she was great!

Reviewed on Dec 8, 2025

Eastwind Windham

Eastwind Windham

2 out of 5
Price was $495, price is now $429 per person
$429
per person
Feb 6 - Feb 8
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
9.2/10 Wonderful! (67 reviews)
Staff helpful and friendly.

Reviewed on Dec 8, 2025

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $570, price is now $497 per person
$497
per person
Feb 6 - Feb 8
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
8.8/10 Excellent! (80 reviews)
Spotless room and great staff

Reviewed on Nov 29, 2025

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Discover the most popular places to visit in Roxbury

Plattekill Mountain

Hit the slopes in Roxbury with a visit to Plattekill Mountain. Discover the mountain views in this relaxing area.

Plattekill Mountain

Roxbury Hotel Deals

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $177 total per night from Dec 15 to Dec 16
$177 total
Dec 15 - Dec 16
Total with taxes and fees
9.2/10 Wonderful! (818 reviews)
The room was comfortable and spacious, but the hallway was very loud at night. It's incredibly close to Hunter Mountain. We enjoyed dinner in the Tavern. Would definitely stay here again!

Reviewed on Dec 7, 2025

Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296 Windham NY
$137 nightly
The price is $148 total per night from Dec 17 to Dec 18
$148 total
Dec 17 - Dec 18
Total with taxes and fees
9.2/10 Wonderful! (713 reviews)
Great place for local skiing. Very little local wifi coverage so make sure you have all your check-in details in advance. Nice spot.

Reviewed on Nov 30, 2025

Hotel Vienna
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
61 LIFTSIDE DR Hunter NY
$218 nightly
The price is $235 total per night from Dec 17 to Dec 18
$235 total
Dec 17 - Dec 18
Total with taxes and fees
9.2/10 Wonderful! (318 reviews)
Beautiful resort.

Reviewed on Dec 6, 2025

Kaatskill Mountain Club at Hunter Mountain
See all 1,455 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.

Find the Best Roxbury Vacation Packages

Roxbury Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Canada Falls, Stamford Golf Club and East Branch Delaware River

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Frequently asked questions

How much does a Roxbury vacation package cost?
You can grab a vacation package to this top destination from $228 on Expedia. But how much your vacation to Roxbury costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Roxbury?
If you're looking to snag a cheap Roxbury vacation package, consider traveling in September, November and December. You're likely to find better rates on airfares and hotels during these months — perfect for budget-conscious travelers.
How many days is enough for Roxbury?
Typically, a handful of days is enough to see the major attractions during your Roxbury vacation. However, if you'd like to have some time to relax or take day trips, think about extending your trip.
How to find the best Roxbury package deals?
Use Expedia's filter tool to find some unbeatable Roxbury package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Roxbury package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually 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 help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a personalized Roxbury vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Roxbury?
If you've got your Roxbury travel dates confirmed, book as soon as you can to bag some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Roxbury?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to go to Roxbury.
  2. Plan your budget wisely: On top of the cost of your stay, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected expenses that may come up during your trip to Roxbury.
  3. Organize your Roxbury getaway with our trip planning tool: Look for and book stays and activities all in one place. You can also collaborate with your group to plan an unforgettable trip to Roxbury together.
  4. Decide how long to go away for: Now that you're more familiar with Roxbury, you can figure out the right length of your vacation. Create a rough itinerary and give yourself enough time to cover everything you want to do.
  5. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Roxbury vacation package for you.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some exciting things to do in Roxbury. Book tickets or make reservations before you go to save time and avoid the stress of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Roxbury vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Roxbury trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.