Round Top Vacations from $627

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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

3 out of 5
Save 100% on your flight
Price was $822, price is now $627 per person
$627
per person
Sep 3 - Sep 7
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.4/10 Exceptional! (808 reviews)
The access to the Windam Path was great. It is a lovely, easy walk by a stream and through meadows.

Reviewed on Jun 19, 2026

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Save 100% on your flight
Price was $1,088, price is now $877 per person
$877
per person
Sep 3 - Sep 7
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
8.8/10 Excellent! (99 reviews)
Beautiful and spacious balcony overlooking the mountains and golf course. We loved the view from our room 521. . Great place to relax before dinner with a glass of wine/cheese. Location is good within walking distance to a most wonderful restaurant named prominence. Highly recommend. The on site restaurant was nice too. Biggest disadvantage was the tv as it does not have any cable and then ending up with no signal at all. Other than that it was a really great place to stay.

Reviewed on Jun 15, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,008, price is now $874 per person
$874
per person
Sep 4 - Sep 7
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
7.6/10 Good! (29 reviews)
I stayed in the mirror cabin everything was great just prepare to have no microwave and or a burner. So you cannot cook or heat anything up. I was able to make it work by just getting stuff that can be eaten cold and then going out to dinner which was fine. Also because the cabin is mirror please note birds constantly fly into it on purpose. It was one bird that every day i was there from morning to night was hitting the glass and it did get very annoying.

Reviewed on Apr 20, 2026

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Round Top Hotel Deals

Riedlbauer's Resort

Riedlbauer's Resort

3 out of 5
57 Ravine Dr. Round Top NY
$177 nightly
The price is $191 total per night from Jun 28 to Jun 29
$191 total
Jun 28 - Jun 29
Total with taxes and fees
8.4/10 Very Good! (98 reviews)
"Our stay was nice and the staff was friendly. The resort had beautiful grounds and lots of things for kids to do. The room was spacious, but it could use some updating. I did not like that there was no refrigerator in the room. I would go back though."

Reviewed on Oct 3, 2025

Riedlbauer's Resort
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
$155 nightly
The price is $168 total per night from Jul 8 to Jul 9
$168 total
Jul 8 - Jul 9
Total with taxes and fees
9.2/10 Wonderful! (975 reviews)
"This lodge is very cozy very clean and great views. Staff was very helpful/ friendly . Such a cute mini getaway spot. Will for sure be coming back"

Reviewed on Jun 20, 2026

Hunter Lodge, a Bluebird by Lark
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$204 nightly
The price is $229 total per night from Jul 16 to Jul 17
$229 total
Jul 16 - Jul 17
Total with taxes and fees
9/10 Wonderful! (515 reviews)
"We stayed in the cabin, very spacious, clean, the bed is so comfortable. The staffs in the center are very friendly and helpful."

Reviewed on Jun 10, 2026

AutoCamp Catskills
See all 2,180 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 $627 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.