8 Charming Resort Towns Where Retirees Can Work Seasonally (And Live There Too)

Dreaming of a stress-free retirement that still keeps you active, social, and maybe even earning a little extra cash?

Seasonal work in resort towns might be just the ticket, giving you the freedom to enjoy beautiful destinations while staying engaged and covering some living expenses. Whether you're pouring coffee at a mountain lodge or greeting guests at a lakeside inn, it's a flexible way to live well without draining your savings.

If your retirement plan includes affordable living with a little more adventure than armchairs, these 8 resort towns are calling your name.

Editor's note: All home prices come from the real estate website Redfin, and cost-of-living data comes from Best Places.

Lake Geneva, near Waterford Township, is a classic Midwest summer getaway, packed with lakefront resorts, beaches, and charming downtown shops. It's a great spot for retirees looking for seasonal work in hospitality, boating, or tourism while soaking up the lake life.

While homes in Waterford Township can be on the pricier side, nearby communities offer more affordable options, and the overall cost of living is manageable. With a median home price of $277,562, it's a fun and scenic place to spend your summers working and relaxing.

North Conway is a year-round playground situated in the White Mountains, offering everything from skiing and snowboarding in winter to hiking and kayaking in summer. It's also a popular shopping destination thanks to its tax-free outlet stores.

For retirees, it's a great place to pick up seasonal work while enjoying small-town charm and mountain views. Additionally, the cost of living here is lower than in many other New Hampshire resort towns, especially across the border in Vermont, making it easier to stay long-term. A two-bedroom unit costs on average $1,240 per month, which is 13.3% cheaper than the national average.

Tucked into the North Georgia mountains, Helen feels like a little slice of Bavaria with its cobblestone streets, vineyards, and Alpine architecture. It's especially lively in the fall and around the holidays, when festivals draw in visitors from all over.

That means plenty of seasonal job opportunities in shops, restaurants, and local events. Whether you're pouring wine at a tasting room or helping with Oktoberfest festivities, Helen offers a fun and festive setting for retirees looking to work and enjoy the mountain lifestyle.

Median home sale prices in Helen are $584,000. You can also rent a two-bedroom there for around $2,000 a month, according to apartments.com.

Sandpoint is a picturesque mountain town in northern Idaho that offers year-round adventure without the sky-high prices of bigger resort areas. In the winter, you'll find skiing and snowboarding at Schweitzer Mountain, and in the summer, Lake Pend Oreille, Idaho's largest lake, becomes the go-to spot for boating, fishing, and beach days.

The town offers a relaxed vibe and a lower cost of living, with the average rental cost of a two-bedroom apartment at $1,130 per month, which is 21.0% lower than the national average, according to Best Places. It's a great option for retirees seeking seasonal work and a scenic place to live, part-time or full-time.

Gulf Shores is a sunny, affordable beach town that shines both in summer and during the winter snowbird season. With its warm weather and abundance of hospitality jobs, it's a great spot for retirees who want seasonal work in restaurants, hotels, or vacation rental management.

Plus, short-term rentals make it easy to live here part-time without a long-term commitment. Renting a two-bedroom unit in Gulf Shores costs $1,240 per month, which is 13.3% cheaper than the national average, according to Best Places. From soaking up the sun to helping guests enjoy their stay, the town offers a laid-back coastal lifestyle at a friendly price.

Hocking Hills is a nature lover's dream, with forests, waterfalls, and scenic hiking trails that come alive in the summer and fall. This affordable Ohio destination draws outdoor enthusiasts from all over, making it a great place for retirees to find seasonal work at cabins, lodges, or within the state park itself.

From greeting guests to helping with events or trail maintenance, there are many ways to stay active. The median home price is around $348,000, making it a budget-friendly option as well.

Bar Harbor is the charming gateway to Acadia National Park, drawing nature lovers and tourists every summer. With its bustling downtown full of shops, restaurants, and tour companies, there's no shortage of seasonal jobs for retirees looking to stay active.

Many employers even offer workforce housing options, making it easier for employees to live close to their workplace. If you love coastal views, fresh seafood, and friendly small-town vibes, Bar Harbor is a fantastic spot to enjoy summer work and play.

The median home sale price is $960,000, so many retirees might prefer to rent a 2-bedroom home, which goes for around $1,210 per month.

South Padre Island is a lively coastal destination that buzzes with activity during the winter and spring months, thanks to winter Texans (snowbirds) and spring breakers alike. For retirees, seasonal work opportunities in hospitality and tourism are plentiful, from beachfront resorts to local restaurants.

Affordable short-term housing options make it easy to live here part-time, while the median home price sits around $547,500.

From mountain escapes to lakeside retreats and coastal getaways, these towns let you live where you love and earn when you want.

If you're planning for retirement but want to stay active and engaged, seasonal work in resort towns offers fun, flexibility, and even affordability if you know where to look.

And keep in mind, many of these communities offer strong retiree networks and activities beyond seasonal jobs, making it easy to build friendships and stay connected all year.