Round Top Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

Find the Best Round Top Vacation Packages

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
The price is ￥20,008 per night from Dec 8 to Dec 9
￥20,008
￥25,010 total
Dec 8 - Dec 9
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"The room was clean and comfortable; however, the lighting was very dim. There was a need for more or brighter lights. The breakfast was good but could have been better. There needed to be more food choices available. The staff was pleasant and helpful."

Reviewed on Nov 6, 2026

Hunter Lodge, a Bluebird by Lark
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

4.5 out of 5
549 Washington Street Hudson NY
Fully refundableReserve now, pay when you stay
The price is ￥33,025 per night from Dec 1 to Dec 2
￥33,025
￥44,437 total
Dec 1 - Dec 2
includes taxes & fees
8.6/10 Excellent! (103 reviews)
"not worth the price!"

Reviewed on Nov 2, 2026

Pocketbook Hotel and Bath
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
The price is ￥23,938 per night from Dec 7 to Dec 8
￥23,938
￥32,658 total
Dec 7 - Dec 8
includes taxes & fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 2,182 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 vacation 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 vacation to Round Top costs.
What are the cheapest months to go to Round Top?
To score cheap Round Top vacation packages, organize 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 vacation. 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 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.
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 accommodations 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 accommodations and airfare: After you've settled on your dates and duration, lock in the perfect Round Top vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.