Round Top Vacations from $275

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Your Round Top Vacation

The artistic creativity, rich history and spectacular views are just some of the reasons why travelers adore this rural city. Discover this wonderful destination the way you want with a Round Top vacation package. Henkel Square Market, Winedale Historical Complex and Copper Shade Tree are just some of the many sights you'll want to see during your trip to Round Top. Whoever you're taking time off with and whatever you plan to spend, your dream Round Top vacation is just a few clicks away with Expedia.

The Latest Round Top vacation packages

Price found within the past 48 hours. Click for updated prices.
Blossom Hotel Houston

Blossom Hotel Houston

4 out of 5
Texas Medical Center
Save 100% on your flight
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Houston (IAH)
9.2/10 Wonderful! (3,362 reviews)
Very clean. Staff very nice, very professional. Rooms were very clean and spacious. AC was great. Won't hesitate to make another reservation there!

Reviewed on Jun 28, 2025

Hotel Saint Augustine

Hotel Saint Augustine

3.5 out of 5
Montrose
Save 100% on your flight
per person
Aug 28 - Sep 2
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Houston (IAH)
9/10 Wonderful! (11 reviews)
My new favorite hotel in Houston

Reviewed on Jun 15, 2025

La Colombe d'Or Hotel

La Colombe d'Or Hotel

5 out of 5
Montrose
Save 100% on your flight
per person
Aug 28 - Sep 2
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Houston (IAH)
9.4/10 Exceptional! (118 reviews)
We stayed in one of the bungalows. It was quiet and relaxing, and the kitchenette and living space were lovely extras that made it feel like home. The location is walkable to several Montrose shops and restaurants, but it feels tucked away in the neighborhood enough that you’d forget you’re in a large city near downtown. I would definitely stay here again.

Reviewed on May 14, 2025

Barsala At Settlers Ranch Apartments

Barsala At Settlers Ranch Apartments

4 out of 5
Southbelt/Ellington
Save 100% on your flight
per person
Aug 7 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Houston (IAH)
10/10 Exceptional! (1 review)
The Hayworth Apartments By Barsala

The Hayworth Apartments By Barsala

3.5 out of 5
Greater Uptown
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Houston (IAH)
No reviews
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Discover the most popular places to visit in Round Top

Winedale Historical Complex

You can learn about the history of Round Top with a visit to Winedale Historical Complex. Experience the area's entertainment venues and festivals.

Winedale Historical Complex

Henkel Square Market

You can find the perfect gifts to bring home at Henkel Square Market during your visit to Round Top. Experience the area's entertainment venues and art scene.

Henkel Square Market

Copper Shade Tree

You can study the exhibits at Copper Shade Tree, a museum with a storied past, during your trip to Round Top. Experience the area's art scene and festivals.

Copper Shade Tree

Round Top Hotel Deals

Round Top Hotel
Round Top Hotel
2 out of 5
701 Texas 237, Round Top, TX
9/10 Wonderful! (63 reviews)
"What an amazing, cute place! Owner was fabulous and super helpful. Seamless experience. Thanks so much for a quiet relaxing visit."

Reviewed on May 31, 2025

Get rates
Round Top Hotel
Flophouze Shipping Container Hotel
Flophouze Shipping Container Hotel
2.5 out of 5
1132 FM 1291 N, Round Top, TX
$263 nightly
The price is $274 total per night from Jun 29 to Jun 30
$274 total
Jun 29 - Jun 30
Total includes taxes and fees
9.6/10 Exceptional! (53 reviews)
"Loved the unique concept and rustic decor. The main inconvenience was no bathroom sink. We had to brush teeth, etc. in kitchen. Also, ceiling fan and shower could have been cleaner. One light bulb in bedroom was broken and just hanging so we didn't turn it on. Overall, we enjoyed our stay."

Reviewed on Aug 21, 2024

Flophouze Shipping Container Hotel
Round Top charm w/POOL and outdoor dining
Round Top charm w/POOL and outdoor dining
Fayette County
9.8/10 Exceptional! (77 reviews)
Perfect farmhouse
"Perfect farmhouse decorated with the best finds. Nicely situated between Warrenton and roundtop"

Reviewed on Nov 3, 2024

Get rates
Round Top charm w/POOL and outdoor dining
See all 605 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
Population
90
Max Temp Winter
60ºF
Max Temp Summer
95ºF
Top Sights
Rohan Meadery, Henkel Square Market and Winedale Historical Complex

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Frequently asked questions

How much does a Round Top vacation package cost?
Offering excellent value package deals from $275 on Expedia, you'll be thrilled with how little a vacation to Round Top costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Round Top?
May, July and December are great times to search for cheap Round Top vacation packages. Traveling in less busy periods means you can generally find lower prices on flights and hotels.
How many days is enough for Round Top?
With a well-organized travel plan, you can easily tick off the top Round Top attractions in a handful of days. But if you'd like to explore off the beaten track or go on day trips, think about booking your Round Top vacation for longer.
Is it worth booking a vacation package to Round Top?
During your Round Top vacation, you can look forward to experiencing some top-notch culture and history. Leave enough room in your itinerary to visit leading sights like Henkel Square Market and Copper Shade Tree.
How to find the best Round Top package deals?
Use Expedia's filters to find some great 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're looking to save, plan your trip for midweek, or browse for Round Top package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Round Top vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can tailor your Round Top getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Round Top?
If you're planning a spur-of-the-moment Round Top vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Round Top?

  1. Choose your travel dates: The things you want to do in Round Top and your favorite season can help you decide when to get away.
  2. Plan your budget wisely: In addition to the price of your accommodations, you should consider other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Round Top.
  3. Explore Round Top with our trip planning tool: Gain insights into the most popular attractions and best properties for your trip to Round Top. You can also save your favorite places, collaborate with your group and organize your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Round Top, you can work out the right length of your break. Create a rough plan and allocate enough time to cover everything you want to see.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Round Top vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some fun things to do in Round Top. Book tickets or make reservations as soon as you can to save time and avoid the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Round Top vacation packages?
Your Round Top trip is meant to be an escape from your busy life, not a source of money worries. So to give you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose 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.