Round Top Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Round Top

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
The price is S$232 per night from 9 Aug to 10 Aug
S$232
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Breakfast set up was very nice - needs to start at 7:00 am"

Reviewed on 11 Jul, 2026

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
The price is S$284 per night from 12 Aug to 13 Aug
S$284
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (526 reviews)
"The AC was too noisy and can’t fall asleep"

Reviewed on 8 Jul, 2026

AutoCamp Catskills
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

3 out of 5
500 Frank Sottile Blvd Kingston NY
Fully refundableReserve now, pay when you stay
The price is S$201 per night from 19 Jul to 20 Jul
S$201
19 Jul - 20 Jul
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Excellent place to stay"

Reviewed on 10 Jul, 2026

Courtyard by Marriott Kingston
See all 2,176 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.

Frequently asked questions

How much does a Round Top holiday package cost?
You'll find cheap prices 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 holiday to Round Top costs.
What are the cheapest months to go to Round Top?
To score cheap Round Top holiday packages, organise your trip outside of peak times such as public holidays. You'll generally find better availability and lower prices for flights and hotels.
How many days is enough for Round Top?
Typically, a handful of days is enough to tick off the major attractions during your Round Top holiday. However, if you want to have some time to chill out or take day trips, think about extending your itinerary.
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 holiday package well in advance.
Is it cheaper to book a Round Top holiday as a package?
Expedia holiday 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 personalised Round Top holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Round Top?
If you're planning an impromptu Round Top holiday, 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.
How to plan a trip to Round Top?

  1. Pick your dates: What you'd like to do in Round Top and your preferred season can help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Round Top.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Round Top. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodation and airfare: After you've settled on your dates and duration, lock in the perfect Round Top holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.