Round Top Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

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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
The price is CA $286 per night from Aug 20 to Aug 21
CA $286
CA $309 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (95 reviews)
"Beautiful property overseen by a lovely person, Wendy was hospitable in every sense of the word; would absolutely love to come back to this amazing retreat in the woods. Also worth mentioning is the amazing waterfall within walking distance of the property."

Reviewed on Jun. 6, 2025

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
The price is CA $185 per night from Sep 11 to Sep 12
CA $185
CA $230 total
Sep 11 - Sep 12
includes taxes & fees
9.2/10 Wonderful! (734 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
The price is CA $179 per night from Sep 8 to Sep 9
CA $179
CA $193 total
Sep 8 - Sep 9
includes taxes & 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
See all 2,085 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.
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Frequently asked questions

How much does a Round Top vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Round Top costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Round Top?
Plan your trip for the low or shoulder season and you're likely to find cheap Round Top vacation packages. Remember that public holidays and local festivals and events can impact prices, so do a little research before booking.
How many days is enough for Round Top?
Generally, a handful of days is enough to check out the major sights during your Round Top vacation. However, if you'd like to have time to chill out or take day tours, think about extending your itinerary.
How to find the best Round Top package deals?
Start your search for a Round Top package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Round Top package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Round Top escape underway.
Is it cheaper to book a Round Top vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can customize your Round Top escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Round Top?
Secure incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Round Top vacation.
How to plan a trip to Round Top?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Round Top.
  2. Plan your budget wisely: As well as the price of your accommodations, you should factor in other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may arise during your trip to Round Top.
  3. Decide how long to go away for: Now that you're more familiar with Round Top, you can work out the perfect length of your vacation. Create a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Round Top vacation package.

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