Valentine’s Day is just around the corner, and you may be wondering how to spend some special time with your darling while continuing to keep yourself and others safe. With the pandemic continuing to challenge us on a daily basis, it can be difficult to decide how to celebrate in a safe, appropriate manner.

If you have a stash of points and miles that you’d like to redeem on a staycation or getaway for Valentine’s Day, there are plenty of options out there. Perhaps this is the year to explore areas in your own backyard, which may allow you to patronize local small businesses on the way.

Here are a few ideas that we hope will give you a bit of inspiration for a Valentine’s Day trip. If you don’t live near these places and want to stick closer to your home this year, we still hope that you’ll draw some motivation from this list and be encouraged to explore our beautiful public lands as well as businesses local to you.

IHG: Holiday Inn Charlottesville – Monticello


Photo Credit: Holiday Inn

If you and your significant other could be described as history buffs or nature enthusiasts, a weekend in Charlottesville could be just the ticket for you two. Book in at the Holiday Inn Charlottesville – Monticello, the closest hotel to Thomas Jefferson’s infamous Monticello plantation.

This property also gives guests excellent access to Shenandoah National Park, which is full of beautiful forest hikes, cascading waterfalls and stunning views of the Blue Ridge mountains. Afterward, take a stroll through the Downtown Mall and pick up some takeout from Revolutionary Soup or The Whiskey Jar to enjoy together back at the hotel. Reward nights start at 12,500 IHG points per night.

Hilton: The Drake

the drake

Photo Credit: Hilton

Easily one of the most iconic, historic hotels in Chicago, The Drake is perfect for a romantic Valentine’s retreat with your dearest. Heading to the heart of a major Midwestern metropolis may not be the best move in the midst of a pandemic, but this property could be ideal for those couples who already live in or near the Windy City.

While the hotel’s on-site services are drastically reduced at this time, The Drake is conveniently located on the north end of the Magnificent Mile with access to exclusive shopping and dining. Take a stroll down Michigan Ave, or simply order in and share a relaxing meal in your gorgeous, comfortable room. Reward nights start at 26,000 Hilton points per night.

Hyatt Regency: Indian Wells Resort & Spa


Photo Credit: Hyatt

Palm Springs is truly a “best of both worlds” type of place because it’s an interesting mix of convenient luxury and expansive desert. One can enjoy all of the modern conveniences of an extravagant resort and escape into the dusty peaks and Joshua tree forests of the Mojave all in the same day.

To take advantage of this unique combination, take your honey to the Indian Wells Resort & Spa in Palm Springs. This is an ideal family property but it’s great for couples, too; enjoy the onsite amenities and nearby high-end shopping districts, or drive up to Joshua Tree National Park for some sandstone bouldering. Whatever your adventure vibe, you and your person can certainly find something to do in Palm Springs. Reward nights start at 20,000 Hyatt points per night.

Wyndham: Ramada Frisco

Ramada by Wyndham Frisco

Photo Credit: Wyndham

The Rocky Mountains are a consistent favorite for winter sports and activities, whether you’re looking to hit the slopes or simply cozy up by the fire with your darling. For a quiet winter retreat with easy access to more famous ski towns but farther away from the crowds, shack up at the Ramada Frisco.

From this property, you’ll have the opportunity to go out on a snowmobiling adventure or pleasant hike, depending on the snow conditions. For a skiing adventure together, note that Frisco is just a quick drive to Keystone, Breckenridge, and Copper Mountain, as well as a reasonable drive to Vail and Avon. Reward nights start at 15,000 Wyndham points per night.

Choice Hotels: Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South

Photo Credit: Quality Inn & Suites Tarpon Springs South

While everybody else is heading to Orlando or Miami, kick just north of Tampa and stay at the Quality Inn & Suites Tarpon Springs South instead. This small Gulf Coast town is most known for sponge diving, making it not only the Sponge Capital of the World but also drawing from strong ties with Greek sponge diving traditions.

With that, it’s easy to find incredibly delicious and authentic Greek food and wine in Tarpon Springs. While in town, don’t miss the chance to dine at Hellas Bakery and Restaurant, which is still open for dine-in. Alternatively, order takeout and enjoy from the sponge docks or your private room near beautiful Lake Tarpon. Reward nights start at 16,000 Choice points per night.

Best Western Plus: River Escape Inn & Suites

Best Western River Escape Inn & Suites

Photo Credit: Best Western Plus River Escape Inn & Suites

Nothing paints a romantic weekend quite like an idyllic stay in Carolina hill country. Nestled along the Tuckasegee River and adjacent to the town of Sylva, the River Escape Inn & Suites is an excellent choice for a quiet, intimate weekend with your sweetheart. Tiny Sylva holds its fair share of hidden gems like Sip’Sum Tea, Guadelupe Cafe, Balsam Falls Brewing Co., and so many more small businesses.

If you’d like to explore the surrounding areas, though, this property stands only ten miles from Cherokee and the border of Great Smoky Mountains National Park. Whether you’d like to enjoy local cuisine or take a pleasant hike, Western Carolina never fails to amaze. Reward nights start at 16,000 Best Western points per night.

Marriott: Springhill Suites Frankenmuth

Marriott Springhill Suites Frankenmuth

Photo Credit: Marriott Springhill Suites Frankenmuth

It’s Valentine’s Day weekend, but if you still aren’t ready to let go of Christmas, head to Springhill Suites Frankenmuth. Surrounded by unassuming Michigan flatlands, this charming Little Bavaria transports visitors to a simpler, tastier, more festive time. Frankenmuth is perhaps most famous for being the host town of Bronner’s, a year-round Christmas shop featuring decorations and ornaments from all around the world.

Downtown, visitors will find quaint boutiques and local shops just across the bridge from two favorite chicken joints: Zehnder’s and the Bavarian Inn. These two restaurants are open for takeout, so put in an order and enjoy from your cozy room. Reward nights start at 18,000 Bonvoy points per night.

The Chase Sapphire Reserve® credit card comes with $300 in annual travel credit, applied automatically each year as a statement credit when you make any qualifying travel purchase. Such travel purchases include airfare and hotel accommodations.

Credit Card Rewards

If you don’t have a stash of rewards points to use towards a stay at a particular hotel, you may also use your general rewards from your credit card rewards programs. Use your Chase Ultimate Rewards points, American Express Membership Points, Citi ThankYou Points, etc. towards booking accommodations from major hotel brands to quaint, boutique properties.

Chase Ultimate Rewards can be transferred to Hyatt, IHG and Marriott, though only Hyatt transfers typically present good value. American Express Membership Rewards can be transferred to Hilton, Choice, and Marriott. Choice points are otherwise somewhat difficult to earn, so that transfer partner can present good value. Temporarily, the transfer ratio to Hilton points is increased, so that may also present reasonable value. Before transferring, it makes sense to compare cash prices.

Also, remember to make good use of your credit card travel benefits! Some travel-aligned rewards cards have travel benefits that are automatically wrapped up within the annual fee.
For example, the Chase Sapphire Reserve® credit card comes with $300 in annual travel credit, applied automatically each year as a statement credit when you make any qualifying travel purchase. Such travel purchases include airfare and hotel accommodations, but now through June 30, gas station and grocery store purchases will also count towards earning this credit.

So, what does this mean for you and your Valentine’s Day trip? Swiping your Chase Sapphire Reserve® at the pump can earn you some free fuel on the way, but if you’re not keen on staying at a hotel these days, you can also use your travel credit towards a private rental. Purchases made through Airbnb, GlampingHub, and OneFineStay all qualify for the CSR travel credit, so you could leverage that credit to get $300 off of your booking.

Bottom Line

Whether your stash of points and miles is brand-specific or good to redeem anywhere, Valentine’s Day weekend is a great time to spend them on a special vacation with your favorite person. Where are you headed this Valentine’s Day?