Round Top Vacations from $526

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Your Round Top Vacation

Come and discover this captivating city for yourself with a Round Top vacation package. Consider spending some time in the neighborhood of Jefferson Heights, which is great for golfing and walking, and your time here is sure to be unforgettable. Fill your spare time with tours of Kaaterskill Falls, North-South Lake Campground & Day Use Area and Mountain Top Arboretum, some of the top attractions you simply have to see during a trip to Round Top. Expedia will help you escape the everyday. Tailor your vacation to Round Top to match your travel style, whatever that may be.

The Latest Round Top vacation packages

Price found within the past 48 hours. Click for updated prices.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Price was $695, price is now $526 per person
$526
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hudson (HCC)
9/10 Wonderful! (423 reviews)
Clean room & pet friendly hotel

Reviewed on Nov 6, 2025

The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $1,594, price is now $1,254 per person
$1,254
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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

Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $681, price is now $563 per person
$563
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hudson (HCC)
9.4/10 Exceptional! (663 reviews)
Great stay but the staff were not very nice and the towels are too small.

Reviewed on Nov 4, 2025

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $761, price is now $637 per person
$637
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hudson (HCC)
8.8/10 Excellent! (74 reviews)
Really nice restored resort. Rooms were great, staff was friendly. The food is very good.

Reviewed on Nov 3, 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 $3,027, price is now $2,553 per person
$2,553
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hudson (HCC)
No reviews
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Round Top Hotel Deals

Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus

2.5 out of 5
430 Winter Clove Road, Round Top, NY
8.8/10 Excellent! (100 reviews)
Fantastic staff, we loved it all except the size of the bathroom and the internet service. The bathroom had barely room for your knees and the shower barely fit my husband who is 230 lbs. Seriously, there was hardly room to turn around in it. And, then there is T-mobile which didn’t help trying when ...

Reviewed on Oct 18, 2025

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Crystal Brook Resort & Mountain Brauhaus
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
$161 nightly
The price is $174 total per night from Nov 23 to Nov 24
$174 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (796 reviews)
I wanted to love this place but didn't. I think we were the wrong demographic (retired seniors) as i believe this would appeal more to younger, more social crowd. Our room, advertised as king mountain view indeed had a living area and a king bed up in a loft. It was nicely maintained. But the windows ...

Reviewed on Oct 30, 2025

Hunter Lodge, a Bluebird by Lark
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212, Saugerties, NY
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $185 total per night from Dec 1 to Dec 2
$185 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (429 reviews)
come here for a short break, love it. it has a grill prepared for u to cook ur own food. great experience, will come again for longer stay.

Reviewed on Oct 13, 2025

AutoCamp Catskills
See all 2,112 properties in Round Top
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 Round Top Vacation Packages

Round Top Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Hunter Mountain, Kaaterskill Falls and Zoom Flume

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Frequently asked questions

How much does a Round Top vacation package cost?
You'll find cheap prices from $526 on Expedia for your Round Top escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Round Top costs.
What are the cheapest months to go to Round Top?
If you'd like to snag a cheap Round Top vacation package, consider traveling in February, March and October. You'll typically find lower rates on accommodations and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Round Top?
The ideal duration for your Round Top vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you plenty of time to visit all the leading sights and explore some hidden gems along the way.
How to find the best Round Top package deals?
Use Expedia's handy filters to find some terrific Round Top package deals. When you begin your search, just 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 browse for Round Top package deals in the off-peak 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 well in advance.
Is it cheaper to book a Round Top vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Round Top vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Round Top?
If you're planning an impromptu Round Top vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Round Top vacation packages?
Your Round Top getaway should be a relaxing escape from your busy life, not a reason for money worries. So to give you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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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.