Roosevelt Roads Ski Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Shannon Willitts
  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 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 flight + Ski hotel deals in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel

Ola Boutique Hotel

Condado
AU$1,014
per person
18 Sept - 20 Sept
found 2 hours ago
Return direct flight included
Baltimore (BWI) to San Juan (SJU)
9/10 Wonderful! (919 reviews)
N/A

Reviewed on 9 Aug 2026

Hotel Puerto Valdes

Hotel Puerto Valdes

Puerta de Tierra
AU$1,032
per person
18 Sept - 20 Sept
found 2 hours ago
Return direct flight included
Baltimore (BWI) to San Juan (SJU)
8.8/10 Excellent! (710 reviews)
I really enjoyed my stay, and the staff made us feel welcomed.

Reviewed on 7 Aug 2026

Aire de O:live

Aire de O:live

Isla Verde
AU$1,144
per person
18 Sept - 20 Sept
found 2 hours ago
Return direct flight included
Baltimore (BWI) to San Juan (SJU)
9.2/10 Wonderful! (725 reviews)
What an amazing experience my wife and I had, from beginning to end. The service was impeccable and made our vacation that much sweeter. The front desk was welcoming from the very start, especially Diane. She made sure we were well accommodated. Every time she saw us she checked in with us to ensure our stay was going well. The location was ideal as it was across from the beach and in the center of the city. There were many restaurants around as well which were walking distance. There was also a Walgreens which was ideal to get essentials. Overall, the experience was over the top and I would absolutely recommend staying at Aire de Olive. We will def be going back especially to see Diane. Thanks for making our experience so sweet Diane!!

Reviewed on 9 Aug 2026

El Conquistador Resort

El Conquistador Resort

Cabezas
AU$1,111
per person
18 Sept - 20 Sept
found 2 hours ago
Return direct flight included
Baltimore (BWI) to San Juan (SJU)
9/10 Wonderful! (3,551 reviews)
Conquistador is our favorite hotel in Puerto Rico, and we have returned several times because we truly enjoy the property and the experience. However, during our most recent stay, we spent two nights in the Marina area and noticed a few issues that I believe the hotel should address. First, the door to our room was not working properly. It would constantly remain open, and we had to use considerable force to close it properly. Even housekeeping left the door open after changing the towels, which was concerning from a security perspective. Also, housekeeping only changed the towels but did not service the room. I’m not sure if this was a new policy or an oversight, but considering the premium price of the hotel, we expect a higher level of service and attention to detail. Finally, the waiting time for the boat to and from Palomino was excessive. I understand that there is currently only one boat operating, but the hotel should reconsider the logistics and find a way to make this process more efficient. The long waits significantly affect the overall experience. We still love El Conquistador and consider it our favorite hotel in Puerto Rico, which is why we hope management takes these comments as constructive feedback. With some improvements in these areas, the experience could once again meet the high standards we have come to expect from the property

Reviewed on 9 Aug 2026

Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

Zarzal
AU$1,079
per person
18 Sept - 20 Sept
found 2 hours ago
Return direct flight included
Baltimore (BWI) to San Juan (SJU)
9/10 Wonderful! (3,176 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all trips

5* Ski holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

Isla Verde
AU$1,094
per person
18 Sept - 20 Sept
found 2 hours ago
Return direct flight included
Baltimore (BWI) to San Juan (SJU)
8.6/10 Excellent! (2,152 reviews)
Pretty good place to stay if it’ll be your first time in Puerto rico… still close to some places but also far enough to feel exclusive.

Reviewed on 9 Aug 2026

Hugo's Rental

Hugo's Rental

Old San Juan
AU$1,909
per person
16 Sept - 22 Sept
found 17 hours ago
Return flight included
Dublin (DUB) to San Juan (SJU)
9.2/10 Wonderful! (339 reviews)
I have stayed at this hotel previously without any issues. This stay was not the same. As I walked in the room you could smell mold. I have allergies and this made it unbearable. It was so bad I had to sleep with a mask.

Reviewed on 21 June 2026

Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

Condado
AU$1,221
per person
18 Sept - 20 Sept
found 2 hours ago
Return direct flight included
Baltimore (BWI) to San Juan (SJU)
9.4/10 Exceptional! (1,795 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all trips

How to find Roosevelt Roads ski packages?

What kind of ski holiday packages are available in Roosevelt Roads?

Expedia offers a wide variety of ski holiday packages. To find out what packages are currently available, just search Expedia for Roosevelt Roads ski packages 2026 and start planning your next ski trip.

How can I book a ski holiday in Roosevelt Roads with Expedia?

Go to the search bar and select “Packages”. Then, choose your destination and the dates of your stay, and browse the list of Roosevelt Roads ski packages to find your perfect ski holiday.

Are ski holidays in Roosevelt Roads suitable for families?

Roosevelt Roads ski holidays can be a great option for families. You can enrol your children in skiing lessons if they’re beginners or spend the days on the slopes with them if they’re already experienced skiers. If your children are too young to ski themselves, look for family-friendly accommodation that offers childcare services and activities for non-skiing family members.

What’s the best way to plan a skiing holiday in in Roosevelt Roads?

Planning a ski holiday to Roosevelt Roads couldn’t be simpler. Just choose your destination and when you want to go, and Expedia will take care of the rest. Once you’ve selected where and when you want to go, Expedia will provide you with several ski packages for that time and place for you to choose from.

What are some tips for choosing a ski package in in Roosevelt Roads?

Before searching for ski packages to Roosevelt Roads, define your priorities. Are you looking for a family-friendly resort, luxury accommodations, budget-friendly options, or specific ski terrain? Knowing your preferences will help you narrow down your choices.

How can I find excellent deals on ski holidays in in Roosevelt Roads?

One of the most reliable ways to get a good deal for 2026 is to book your Roosevelt Roads ski holiday well in advance. Resorts often offer early booking discounts, and you’ll have a wider selection of accommodations to choose from.

How can I grab last-minute ski holiday deals in Roosevelt Roads?

Just enter your dates and see what’s available. This way you might be able to nab some great last-minute Roosevelt Roads ski packages.

Are pet-friendly ski holiday packages available in Roosevelt Roads?

To find pet-friendly Roosevelt Roads ski packages in 2026, once you’ve entered your dates, use the filters on the left and select “Pet-friendly” under “Amenities” and the pet-friendly ski resort packages will show up.

How can I find great weekend ski holiday packages in Roosevelt Roads?

Enter your weekend dates and search Expedia’s Roosevelt Roads ski trip packages to find the ones that are available for the weekend of your choice. You can sort by price to find Roosevelt Roads ski holidays that suit your wallet.

How can I find the cheapest ski holidays in in Roosevelt Roads?

Once you’ve entered your travel dates, use the sort by filter at the top right to sort by price and find Roosevelt Roads ski holidays that won’t break the bank. Plus, booking well in advance can help you find cheaper rates. Be sure to check out Expedia’s Roosevelt Roads ski packages including flights as you could save money by booking everything together.

Why should I book a ski holiday package in Roosevelt Roads with Expedia?

Expedia lets you bundle up your stay, flight, and car rental for some cool discounts on Roosevelt Roads ski packages that will have you carving through the powder without burning a hole in your pocket.

Can I cancel my ski holiday booking in Roosevelt Roads with Expedia?

Yes, numerous Roosevelt Roads ski packages offer free cancellation, giving you the freedom to put the brakes on your trip in the event of unforeseen circumstances.

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