Round Top Vacations from $457

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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 $589, price is now $457 per person
$457
per person
Mar 23 - Mar 28
found 10 hours ago
Roundtrip flight included
Norfolk (ORF) to Hudson (HCC)
9.4/10 Exceptional! (699 reviews)
Such a cute get away! I loved it

Reviewed on Jan 18, 2026

Deer Mountain Inn

Deer Mountain Inn

2 out of 5
Save 100% on your flight
Price was $1,411, price is now $1,051 per person
$1,051
per person
Mar 23 - Mar 28
found 10 hours ago
Roundtrip flight included
Norfolk (ORF) to Hudson (HCC)
9/10 Wonderful! (4 reviews)
I loved the guest room with the pool table and self attend bar.

Reviewed on Oct 22, 2024

Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was $777, price is now $599 per person
$599
per person
Mar 23 - Mar 28
found 10 hours ago
Roundtrip flight included
Norfolk (ORF) to Hudson (HCC)
9.2/10 Wonderful! (314 reviews)
Get some bottled water

Reviewed on Jan 14, 2026

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
Price was $638, price is now $542 per person
$542
per person
Mar 23 - Mar 28
found 10 hours ago
Roundtrip flight included
Norfolk (ORF) to Hudson (HCC)
9.2/10 Wonderful! (808 reviews)
We expected a fuller breakfast menu like we've had in the past at this hotel.

Reviewed on Jan 20, 2026

SunView Motel

SunView Motel

2.5 out of 5
Price was $569, price is now $503 per person
$503
per person
Mar 23 - Mar 28
found 10 hours ago
Roundtrip flight included
Norfolk (ORF) to Hudson (HCC)
8.6/10 Excellent! (559 reviews)
Sun View is a great place to stay when skiing at Hunter Mtn. The rooms can easily handle 4 adults with ski equipment. Plenty of places to eat nearby. Will definitely stay here again in the future.

Reviewed on Jan 5, 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
$169 nightly
The price is $183 total per night from Jan 22 to Jan 23
$183 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
$131 nightly
The price is $147 total per night from Jan 26 to Jan 27
$147 total
Jan 26 - Jan 27
Total with taxes and fees
8.8/10 Excellent! (824 reviews)
The room was very clean. Nice amenities. The staff at the desk were very pleasant and helpful

Reviewed on Jan 17, 2026

Residence Inn by Marriott Kingston
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296 Windham NY
$159 nightly
The price is $172 total per night from Jan 22 to Jan 23
$172 total
Jan 22 - Jan 23
Total with taxes and fees
9.2/10 Wonderful! (746 reviews)
Such a cute get away! I loved it

Reviewed on Jan 18, 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 $457 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.