Roxbury Vacations from $442

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The Latest Roxbury vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Save 100% on your flight
Price was $616, price is now $442 per person
$442
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
9.4/10 Exceptional! (605 reviews)
Beautiful property. Lovely room with a very comfortable bed. Extremely helpful desk staff—I would like to extend my thanks especially to her.

Reviewed on Aug 20, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
Price was $927, price is now $599 per person
$599
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
9/10 Wonderful! (409 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug 7, 2025

The Hidden Inn

The Hidden Inn

4 out of 5
Save 100% on your flight
Price was $722, price is now $479 per person
$479
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
9.4/10 Exceptional! (37 reviews)
The staff was great. There has to be a better communication between the hotel and expedia.

Reviewed on Aug 20, 2025

Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Save 100% on your flight
Price was $710, price is now $492 per person
$492
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
9.2/10 Wonderful! (259 reviews)
Great place to rest and relax if this is what you want to do. I would highly recommend. They have great facilities at the hotel the hot tub and steam room was a hit for us. The property is very quiet and serene.

Reviewed on Aug 19, 2025

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $1,295, price is now $924 per person
$924
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hudson (HCC)
9.4/10 Exceptional! (164 reviews)
Loved everything about it, especially large deck with view of waterfall. Interiors were beautiful and contemporary in a very convenient and comfortable way. No negatives.

Reviewed on Aug 18, 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
$169 nightly
The price is $183 total per night from Aug 25 to Aug 26
$183 total
Aug 25 - Aug 26
Total includes taxes and fees
9.2/10 Wonderful! (736 reviews)
"Nice lodge with a great view. Staff was very friendly."

Reviewed on Aug 16, 2025

Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
$122 nightly
The price is $132 total per night from Sep 21 to Sep 22
$132 total
Sep 21 - Sep 22
Total includes taxes and fees
9.2/10 Wonderful! (618 reviews)
"Hotel was very clean, grounds looked great and the owner/manager was constantly waiting on guests."

Reviewed on Aug 16, 2025

Hotel Vienna
Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
37 Alpine Rd, Big Indian, NY
$170 nightly
The price is $190 total per night from Aug 25 to Aug 26
$190 total
Aug 25 - Aug 26
Total includes taxes and fees
9.2/10 Wonderful! (161 reviews)
"The staff here was amazing, had a great one night getaway and I wished we stayed longer! Definitely would come back! Service A plus! Food A plus! Scenery outstanding! Definitely recommend for a good wind down from ones busy day to day."

Reviewed on Aug 15, 2025

Urban Cowboy Lodge
See all 1,442 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.

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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 $442 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.