Round Top Vacations from $559

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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.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $632, price is now $559 per person
$559
per person
Feb 19 - Feb 22
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Hudson (HCC)
9.4/10 Exceptional! (699 reviews)
Really nice and clean room! And the front desk was very nice and helpful!

Reviewed on Jan 17, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,137, price is now $955 per person
$955
per person
Feb 19 - Feb 22
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Hudson (HCC)
8.6/10 Excellent! (17 reviews)
I loved the view and the area

Reviewed on Jul 31, 2025

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $792, price is now $711 per person
$711
per person
Feb 19 - Feb 22
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Hudson (HCC)
8.8/10 Excellent! (80 reviews)
This place is GREAT!! Outstanding room, top notch service, cool staff, and good food!! Mmm mm!! I'm ready to go again!!

Reviewed on Jan 10, 2026

Hunter Mountain Ski House - Tesla Charger

Hunter Mountain Ski House - Tesla Charger

2 out of 5
Save 100% on your flight
Price was $2,426, price is now $2,204 per person
$2,204
per person
Feb 19 - Feb 22
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Hudson (HCC)
No reviews
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was $814, price is now $744 per person
$744
per person
Feb 19 - Feb 22
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Hudson (HCC)
9.2/10 Wonderful! (314 reviews)
Get some bottled water

Reviewed on Jan 14, 2026

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Round Top Hotel Deals

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$150 nightly
The price is $162 total per night from Jan 22 to Jan 23
$162 total
Jan 22 - Jan 23
Total with taxes and fees
9.4/10 Exceptional! (127 reviews)
The stay was wonderful. The beautiful place. All very comfortable!

Reviewed on Jan 13, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Jan 25 to Jan 26
$142 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (821 reviews)
You can tell they take care of the property

Reviewed on Jan 7, 2026

Residence Inn by Marriott Kingston
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296 Windham NY
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $172 total per night from Jan 20 to Jan 21
$172 total
Jan 20 - Jan 21
Total with taxes and fees
9.2/10 Wonderful! (740 reviews)
Nice rooms and continental breakfast. Very reasonable price.

Reviewed on Jan 13, 2026

Hotel Vienna
See all 2,140 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 $559 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.