Round Top Vacations from $530

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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
Price was $566, price is now $530 per person
$530
per person
Jul 6 - Jul 8
found 10 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.4/10 Exceptional! (799 reviews)
Clean room, friendly and helpful staff

Reviewed on May 20, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $687, price is now $601 per person
$601
per person
Jul 6 - Jul 8
found 10 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
7.8/10 Good! (28 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

Red Feather Lodge

Red Feather Lodge

3 out of 5
Price was $2,540, price is now $2,281 per person
$2,281
per person
Jul 6 - Jul 8
found 10 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $772, price is now $705 per person
$705
per person
Jul 6 - Jul 8
found 10 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
8.8/10 Excellent! (97 reviews)
Family Weekend Getaway. This is our 4th time at this property. Our first time was a year ago during Memorial Day Weekend. Although it was a very droopy weekend, Wylder made it an unforgettable moment . Enough to come back several times. May 16 weekend was one if the best, the weather was perfect, the food as always delicious and the staff amazing. Wylder will always be a perfect location with or without kids/furry babies . I am all ready looking for our next weekend getaway.

Reviewed on May 18, 2026

Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $640, price is now $607 per person
$607
per person
Jul 6 - Jul 8
found 10 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.2/10 Wonderful! (102 reviews)
Clean and such friendly staff would definitely recommend! But the prices are little too high in my opinion

Reviewed on Apr 26, 2026

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Round Top Hotel Deals

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
$135 nightly
The price is $146 total per night from Jun 2 to Jun 3
$146 total
Jun 2 - Jun 3
Total with taxes and fees
9.2/10 Wonderful! (945 reviews)
"Clean room, beautiful property, outstanding staff….no elevator and no handicap access to rooms on ground level. Otherwise I would have stayed longer."

Reviewed on May 19, 2026

Hunter Lodge, a Bluebird by Lark
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
$134 nightly
The price is $150 total per night from May 31 to Jun 1
$150 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (930 reviews)
"This hotel is playing some game with their indoor pool, which is closed for no reason. It is stated on their website that pool is closed for the renovation but there in no work is happening. Pool is in a very good condition, hotel just cover front windows with a paper. Also breakfast was poor."

Reviewed on May 18, 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
$192 nightly
The price is $207 total per night from Jun 22 to Jun 23
$207 total
Jun 22 - Jun 23
Total with taxes and fees
9.6/10 Exceptional! (232 reviews)
"Enjoyed my stay staff was attentive!"

Reviewed on May 22, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 2,162 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 $530 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.