Round Top Vacations from $1,571

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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.
Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House

Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House

3 out of 5
Save 100% on your flight
Price was $2,026, price is now $1,571 per person
$1,571
per person
May 5 - May 9
found 1 hour ago
Roundtrip non-stop flight included
Savannah (SAV) to Hudson (HCC)
No reviews
Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

3 out of 5
Save 100% on your flight
Price was $5,147, price is now $3,715 per person
$3,715
per person
May 5 - May 9
found 1 hour ago
Roundtrip non-stop flight included
Savannah (SAV) to Hudson (HCC)
No reviews
Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

3 out of 5
Save 100% on your flight
Price was $5,435, price is now $4,082 per person
$4,082
per person
May 5 - May 9
found 1 hour ago
Roundtrip non-stop flight included
Savannah (SAV) to Hudson (HCC)
No reviews
Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

3 out of 5
Save 100% on your flight
Price was $5,320, price is now $4,002 per person
$4,002
per person
May 5 - May 9
found 1 hour ago
Roundtrip non-stop flight included
Savannah (SAV) to Hudson (HCC)
No reviews
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
Price was $3,308, price is now $2,649 per person
$2,649
per person
May 5 - May 9
found 1 hour ago
Roundtrip non-stop flight included
Savannah (SAV) to Hudson (HCC)
No reviews
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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
$118 nightly
The price is $132 total per night from Mar 15 to Mar 16
$132 total
Mar 15 - Mar 16
Total with taxes and fees
9/10 Wonderful! (872 reviews)
Room was super big and spacious. The bed was so comfortable and the shower was perfect and clean

Reviewed on Mar 11, 2026

Residence Inn by Marriott Kingston
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
$141 nightly
The price is $152 total per night from Mar 18 to Mar 19
$152 total
Mar 18 - Mar 19
Total with taxes and fees
9.6/10 Exceptional! (171 reviews)
A very cozy cabin! We loved how spread out they were and had privacy and quiet. Beautiful view! Well equipped for cooking/grilling dinner and simple breakfasts. Could use a good deep clean. I understand it’s glamping but the built up dust in spots and the vents was a little gross.

Reviewed on Mar 10, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$170 nightly
The price is $191 total per night from Apr 8 to Apr 9
$191 total
Apr 8 - Apr 9
Total with taxes and fees
9/10 Wonderful! (463 reviews)
Amazing experience, Elena was great, very helpful and cheerful.

Reviewed on Mar 13, 2026

AutoCamp Catskills
See all 2,131 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 $1,571 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.