Roxbury Vacations from $621

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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
Price was $740, price is now $621 per person
$621
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hudson (HCC)
8.8/10 Excellent! (51 reviews)
We arrived at night in time for a cocktail and an appetizer.Everything was great .Room was immaculate and quiet. Would definitely stay again if in area .

Reviewed on Oct 10, 2025

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

3 out of 5
Save 100% on your flight
Price was $2,877, price is now $2,056 per person
$2,056
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
10/10 Exceptional! (1 review)
We encountered issues with the kitchen lightings and dish washer. Other than that, the house is beautiful and spacious.

Reviewed on Sep 27, 2025

The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $2,828, price is now $2,142 per person
$2,142
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
8.6/10 Excellent! (15 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

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

2 out of 5
Save 100% on your flight
Price was $6,020, price is now $4,612 per person
$4,612
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
No reviews
Perfect Family Vacation Home in the Mountains

Perfect Family Vacation Home in the Mountains

2 out of 5
Price was $1,582, price is now $1,375 per person
$1,375
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hudson (HCC)
No reviews
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Discover the most popular places to visit in Roxbury

Plattekill Mountain

4.5/5(35 reviews)

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
$118 nightly
The price is $128 total per night from Nov 11 to Nov 12
$128 total
Nov 11 - Nov 12
Total with taxes and fees
9.2/10 Wonderful! (784 reviews)
Lovely overnight stop for us traveling through the Catskills. Love the dark rich lodge colors and decor. Room was big with nice toiletries.

Reviewed on Oct 16, 2025

Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $120 total per night from Nov 24 to Nov 25
$120 total
Nov 24 - Nov 25
Total with taxes and fees
9.2/10 Wonderful! (676 reviews)
Perfect Romantic Getaway! We had an amazing stay at the Vienna Hotel in Windham — cozy, spotless rooms and a warm, welcoming atmosphere. It’s the perfect romantic escape, close to Hunter Mountain and local restaurants but peaceful and relaxing. Loved the thoughtful touches like the complimentary ...

Reviewed on Oct 20, 2025

Hotel Vienna
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
61 LIFTSIDE DR, Hunter, NY
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $212 total per night from Oct 29 to Oct 30
$212 total
Oct 29 - Oct 30
Total with taxes and fees
9/10 Wonderful! (300 reviews)
Great stay

Reviewed on Oct 18, 2025

Kaatskill Mountain Club at Hunter Mountain
See all 1,441 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 $621 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.