5 Timeless Romance Movies to Watch This Valentine’s Day, Featuring Historic Hotel Settings

While I know Valentine’s Day is considered a Hallmark holiday, I absolutely love it! It’s a great excuse to show the special people in your life how much you love them. And I love being able to sit down and watch a good romance movie, whether with some girlfriends, or at home with Dane.

Classic romance films are the perfect companion for a celebration of love, offering a beautiful escape to timeless stories of love. They often feature romantic getaways and historic hotels from the 1800s, providing a backdrop of elegance, charm, and unforgettable moments. Whether in lavish ballrooms or cozy suites, these films take us to a more romantic era, where love is not just a feeling, but a beautifully crafted experience.

So, if you’re looking for a good movie to watch this Valentine’s Day and want to avoid spending hours scrolling through options, I put together a fun list of five classic romance movies that I love and hope you will too!

1. The Philadelphia Story: A Classic Love Triangle

Cary Grant, James Stewart, and Katherine Hepburn all in one movie?! Count me in! The Philadelphia Story is a classic love triangle filled with slapstick humor and banter you can’t help but enjoy! The story follows a high society woman preparing to marry her wealthy fiancé, with plans thrown into disarray by her ex-husband and a reporter. The story takes place in a family mansion, which, while not a hotel, evokes the grandeur and opulence of a historic estate, similar to the kind of lavish settings you might find in a grand hotel.

I teach a Film Studies class at my high school and we watch this one every year. There’s so much great dialogue and subtle humor, you may even want to watch it twice! Also, if you want the same story and script, but with a musical element, the movie, High Society, is pretty much a copy paste film, but with Frank Sinatra, Bing Crosby, and Grace Kelly in the lead roles.

Where to stream: Tubi (free), Amazon Prime Video (rental fee), Apple TV (rental fee)

2. Somewhere in Time: A Timeless Love Story Set in Michigan’s Iconic Hotel

Somewhere in Time is a beautifully-crafted, timeless romantic drama that transports viewers into a world of love, longing, and the magic of time travel. And did I mention that it takes place in a historic hotel?! Christopher Reeve and Jane Seymour deliver exceptional performances, following a playwright who falls in love with a woman from a different era.

The Grand Hotel in Mackinac Island, Michigan

My favorite aspect of this film is that it is set at the incredible Grand Hotel on Mackinac Island in Michigan. (If you’ve never been to Mackinac Island, it is definitely worth a day or weekend trip!) Somewhere in Time is a great love story in a beautiful setting, a perfect watch for Valentine’s Day!

Where to stream: Tubi (free), Amazon Prime Video (rental fee), Apple TV (rental fee)

3. The Harvey Girls: Romance in the Old West and Railroad Hotels

I couldn’t make a list of classic romance movies without including a Judy Garland film! I personally think The Harvey Girls is one of Judy’s most underrated films. It’s a western and romance all in one. (If you have trouble getting your man to watch a romantic movie on Valentine’s Day, just tell him it’s a western!)

Judy Garland’s character travels out west to meet the man she’s been exchanging letters with, but she quickly learns that he didn’t write the letters, and that is only the beginning of her troubles. The film combines humor, romance, and Western flair, and keeps you engaged from start to finish.

The Harvey Girls trailer on YouTube

The Harvey Girls is also set around the opening of a Harvey House, a series of hotels and restaurants along the Atchison, Topeka, and Santa Fe Railroad in the late 1800s. These real-life establishments played a key role in providing high-quality meals and services to travelers across the American West, similar to the theme of the movie, where the women work at one of these railroad dining establishments.

Where to stream: Max (free), Hulu (premium subscription), Amazon Prime Video (rental fee), Apple TV (rental fee)

4. To Catch a Thief: Romance and Thrills Set in Luxurious Hotels

While Alfred Hitchcock is renowned for his thrillers and suspense films, he also crafted several captivating romances, and To Catch a Thief is one of them. Starring Cary Grant and Grace Kelly, this film is a perfect showcase of their undeniable chemistry and charisma. Grant, playing a retired jewel thief suspected of returning to his criminal ways, is charming and suave, while Kelly shines as a wealthy, adventurous woman who becomes entangled in his web of intrigue. If you’re looking for a dash of thrill with your romance film this Valentine’s Day, look no further!

To Catch a Thief also has a connection to the luxurious hotels of the French Riviera, particularly the Hotel Belle Côte in the movie, where much of the action takes place. The hotel is central to the film’s glamorous setting, and the high-end atmosphere of the hotel mirrors the sophistication and allure of the plot.

Where to stream: YouTube (rental fee), Apple TV (rental fee)

5. An Affair to Remember: Timeless Love and Iconic Scenes

And last, but certainly not least, is my favorite film recommendation for Valentine’s Day! An Affair to Remember is a timeless, romantic masterpiece with its heartfelt story and unforgettable performances. Starring Cary Grant (yes, by now you know I’m a big Cary Grant fan!) and Deborah Kerr, the film weaves a tender tale of love, longing, and fate, making it one of the most beloved romance films of all time.

Although the main setting of An Affair to Remember isn’t a historic hotel, the iconic scene where Cary Grant and Deborah Kerr agree to meet at the Empire State Building is reminiscent of the kind of romantic hotel rendezvous found in many classic films. The luxurious New York setting adds to the overall romantic and elegant feel of the movie, even though the plot itself doesn’t revolve around a hotel.

I will warn you, this film is a tear jerker, or at least for me; I cry everytime I watch it. And I couldn’t recommend this film without also suggesting that you make it a double feature and watch Sleepless in Seattle right after, which is somewhat of a modern take on the film and makes many references to An Affair to Remember throughout.

Where to stream: Netflix (free), Amazon Prime Video (rental fee)


Ready for a romantic story of your own?

Room 205 decorated as the Art District Suite in the Knox Hotel

The Knox Hotel can be part of your own elegant, romantic getaway! Not only can you experience a stay amidst lavish Victorian ambiance, but you can watch any of the films mentioned above by borrowing them from our DVD collection. And even better, we partner with our neighbor Beetz Me to offer delicious wine and charcuterie that pair perfectly with the timeless love stories!