Round Top Vacations from $576

Book a Hotel + Flight or Car together to unlock savings

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.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.2/10 Wonderful! (259 reviews)
Every thing was fine Suggest better television options Suggest refrigerator in room

Reviewed on Aug 6, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9/10 Wonderful! (409 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug 7, 2025

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

3 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.4/10 Exceptional! (164 reviews)
Spacious room, walkable to everything, but tucked away. Perfect.

Reviewed on Aug 11, 2025

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

3 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews
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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
Fully refundable
$207 nightly
The price is $224 total per night from Aug 18 to Aug 19
$224 total
Aug 18 - Aug 19
Total includes taxes and 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
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $183 total per night from Sep 11 to Sep 12
$183 total
Sep 11 - Sep 12
Total includes taxes and fees
9.2/10 Wonderful! (730 reviews)
"Great location. Beautiful resort. Great and helpful staff"

Reviewed on Aug 13, 2025

Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $145 total per night from Aug 25 to Aug 26
$145 total
Aug 25 - Aug 26
Total includes taxes and fees
9.2/10 Wonderful! (616 reviews)
"Great hotel"

Reviewed on Aug 12, 2025

Hotel Vienna
See all 2,081 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?
You'll find cheap prices from $576 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.