Round Top Vacations from $261

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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.
The Hidden Inn

The Hidden Inn

4 out of 5
Save 100% on your flight
Price was $344, price is now $261 per person
$261
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
9/10 Wonderful! (56 reviews)
Perfect accommodations when visiting relatives in the area.

Reviewed on Nov 30, 2025

The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $547, price is now $401 per person
$401
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
8.6/10 Excellent! (20 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

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
Price was $405, price is now $297 per person
$297
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
9/10 Wonderful! (433 reviews)
Every time I'm looking for a quick, quiet getaway, this is my place. I love that my dog was able to join me and different types of camping rooms are available to choose from. I loved the space of the family cabin and the perfect size kitchen for our specific needs (morning coffee, late dinner), but unfortunately my bed had hair under the covers and my mom woke up with bites on her ankles. However, I will still choose Auto Camp as a getaway spot, I will just double check our room before agreeing to the room.

Reviewed on Dec 20, 2025

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $568, price is now $461 per person
$461
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
9.6/10 Exceptional! (205 reviews)
The room and views were lovely, and we loved the Tannery cafe!

Reviewed on Dec 12, 2025

Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $318, price is now $264 per person
$264
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
9.4/10 Exceptional! (699 reviews)
Great service, nice and clean hotel.

Reviewed on Dec 21, 2025

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Round Top Hotel Deals

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
$114 nightly
The price is $128 total per night from Jan 1 to Jan 2
$128 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (790 reviews)
Everything was great. Fantastic breakfast. Fire alarm went off the first night we were there and we had to wait till that was over but other than that everything was good

Reviewed on Dec 8, 2025

Residence Inn by Marriott Kingston
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
$174 nightly
The price is $188 total per night from Jan 4 to Jan 5
$188 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (823 reviews)
I loved this hotel! It definitely gives mountain vibes, the decor is perfect. The shower and beds were excellent, the service and the staff are amazing. I was pleasantly surprised - I can be very particular with my hotel stays, I want it to be at least as comfortable as home if not better. Between ...

Reviewed on Dec 14, 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
$209 nightly
The price is $234 total per night from Jan 11 to Jan 12
$234 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.8/10 Excellent! (442 reviews)
Every time I'm looking for a quick, quiet getaway, this is my place. I love that my dog was able to join me and different types of camping rooms are available to choose from. I loved the space of the family cabin and the perfect size kitchen for our specific needs (morning coffee, late dinner), but ...

Reviewed on Dec 20, 2025

AutoCamp Catskills
See all 2,111 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 $261 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.