I grew up just outside of Philadelphia, and I often seek out small-town travel experiences. Maine — specifically the state’s charming coastal towns — has always been on my bucket list of places I’ve wanted to explore.

Fresh off the heels of the peak summer travel months, I found myself in the small, idyllic seaside town of Kennebunkport, Maine. Visiting the weekend after Labor Day, considered “shoulder season” for this popular destination, I was able to enjoy all that the New England state’s shoreside town had to offer — without the traffic of summer tourists or fall foliage seekers.

Situated less than two hours from Boston, Kennebunkport is a sweet town that features sandy beaches, local artisanal shops and the iconic Walker’s Point Estate (also known as the Bush family compound).

Planning a trip to the affluent area of southern Maine can be costly, especially when you have to factor in flights, a rental car and your hotel stay. Luckily, if you have a travel rewards credit card, like the Chase Sapphire Reserve® (see rates and fees), you can use a combination of Chase Ultimate Rewards points and statement credits to save upward of $2,600.

Here are my hacks for booking your next weekend getaway to Maine’s coastal hot spots, sans the high prices.

Related: The best coastal hotels to visit during your next seaside getaway

Use your points or miles to book round-trip flights

As a current Florida resident, driving to Maine was not an option, so I had to book round-trip flights for myself, my partner and our (now) 8-month-old son. JetBlue operates direct flights from Fort Lauderdale-Hollywood International Airport (FLL) to Boston Logan International Airport (BOS). Though I could have opted to fly to Portland International Jetport (PWM) — which is only about a 30-minute drive to Kennebunkport — the flights were not direct, and it was a bit more expensive.

I booked two round-trip Blue Basic tickets for a total of 26,000 JetBlue TrueBlue points plus $22 in taxes and fees. Cash prices for the round-trip tickets cost about $192 per person, or 13,000 TrueBlue points. I already had 7,000 TrueBlue points in my account and really wanted to save money on the flights.

Chase points transfer to TrueBlue at a 1:1 ratio; however, per TPG’s September 2025 valuations, Ultimate Rewards points are worth 2.05 cents per point while TrueBlue points are worth 1.45 cents apiece. Therefore, if I transferred my Chase points, I would lose some value. Alas, I was set on simply saving money for this quick trip and transferred 19,000 points to book two award flights plus taxes and fees, saving $362.

Related: 21 ways to use 100,000 Chase Ultimate Rewards points

As a budget-conscious traveler and points and miles enthusiast, I always try and maximize my rewards. But at the end of the day, sometimes it’s just about saving myself a few extra bucks and not hoarding my points because of analysis paralysis.

So, if you’re looking to book flights to Maine, points and miles can save you money. To help with your flight searches, try using an award tool like Seats.aero or Going to help find great deals.

Related: I was sitting on 150,000 credit card points — how I got past analysis paralysis to redeem them

Book a rental car for your trip using statement credits

The drive from Boston to Kennebunkport is about two hours, so booking a rental car was a must. Plus, we planned to explore neighboring areas like the town of Ogunquit and take a quick 30-minute ride to Portland for some incredible restaurants.

While you can opt to book a rental car using points or miles through a travel portal, such as Chase Travel℠, American Express Travel or Capital One Travel, you can also save money by utilizing statement credits on certain credit cards.

For example, the Chase Sapphire Reserve offers an annual $300 travel statement credit. Similarly, the Capital One Venture X Rewards Credit Card offers a $300 travel credit per cardmember year on bookings made through the Capital One Travel portal. Therefore, if you pay for your rental car using your card, you can potentially cover most (if not all) of your rental car expenses.

Related: Save money on your next trip: Use these tips to never pay full price for a rental car

Though Kennebunkport is a walkable town, being able to venture outside of the area to neighboring antique shops, the overlook near the Bush family compound and nearby destinations like Ogunquit and Portland will enhance your coastal road trip (more on this below).

Where to stay: Kennebunkport Captains Collection

Kennebunkport and the surrounding town of Ogunquit are home to dozens of locally owned shops and restaurants. With this emphasis on local business, you won’t find a McDonald’s or Target when you’re walking through the dockside areas. But, when it comes to booking your stay, despite the lack of hotels from major brands like Hilton, Hyatt and Marriott, there is one boutique hotel that you can actually book in the heart of Kennebunkport’s downtown area using World of Hyatt points.

Kennebunkport Captains Collection overview

The Kennebunkport Captains Collection is part of the Mr & Mrs Smith portfolio, a collection of luxury boutique properties that now partners with Hyatt. Therefore, you can redeem Hyatt points for a stay at this beautiful and historic hotel.

Built in the early 19th century, four stately houses were constructed and passed down to Kennebunkport’s seafaring families. These settlements eventually became boutique inns and in 2021, part of Lark Hotels (also part of Mr & Mrs Smith).

Related: Our favorite Mr & Mrs Smith hotels to book using Hyatt points

Featuring colonial-style architecture and rustic decor combined with modern amenities like LED TVs and plush bedding, Kennebunkport Captains Collection is the ideal place to immerse yourself in the maritime aesthetic of this seaside town.

When you stay at this hotel, your room will be located in one of the four houses, and each house has its own unique style and personality. On arrival, you’ll check in at Nathaniel Lord Mansion, a bright yellow colonial house with black shutters and moody decor.

I stayed in William Jefferds House, which featured a bright white interior and a more modern feel, a stark departure from the other homes on the property. My room, the Jefferds Deluxe King, featured a king-size bed, a walk-in shower with Lather apothecary products, robes, two sitting chairs and a TV. Most notably, a fireplace was situated at the center, which brought an extra sense of hominess to the room.

Per the hotel’s website, most rooms within the four homes feature a fireplace.

Each homestead also has common sitting areas where you can chat and admire the eclectic architecture and decor — or enjoy your complimentary breakfast and coffee. Again, since the living room and kitchen area (specifically for my stay, the sunroom in the William Jefferds House) are operating in a homelike space compared to a standard Hyatt hotel with extra-large rooms, I found myself engaging with other guests more because of these intimate spaces.

Each morning, while dining on an egg quiche and fresh fruit with granola, I learned who was vacationing at Kennebunkport Captains Collection for the fifth time, recommendations on dinner restaurants in the neighboring town and where to get the best lobster roll (Footbridge Lobster in Ogunquit came highly recommended).

Overall, the cozy and historical colonial aesthetic of Kennebunkport Captains Collection elevated my stay. It was a departure from the standard hotel vibe, yet still included all of the modern hotel amenities a guest would yearn for, including complimentary beach chairs and bike rentals (remember, Kennebunkport is a beach town). And the best part about this hotel: You can book it using points.

How to book with Hyatt points

Unlike other Hyatt properties, which use a fixed award chart, Mr & Mrs Smith hotels operate using dynamic pricing. Therefore, getting value from your Hyatt points can prove challenging. Nevertheless, booking during Maine’s shoulder season at a Mr & Mrs Smith property can have its perks. While rates for each room fluctuate, I found that you could book a room at this hotel in early September for 35,250 Hyatt points or $623 per night. This would give you a value of about 1.76 cents per point, which is a pretty good redemption since TPG values Hyatt points at 1.7 cents apiece per our September 2025 valuations.

Therefore, for three nights, you could redeem 105,750 Hyatt points and save about $1,900. Since breakfast is included in your stay, that is another expense that can be cut from your budget

Even if you don’t have enough Hyatt points, Chase Ultimate Rewards points transfer to Hyatt at a 1:1 ratio. Therefore, if you earned the welcome bonus on the Chase Sapphire Reserve — applicants can earn 125,000 points after spending $6,000 on purchases within the first three months from account opening — you could book a three-night stay at this luxury boutique property.

Plus, at that rate, you could potentially book your flight and a rental car with the leftover points and your $300 travel credit.

Note that since this property uses dynamic award pricing, your stay could require more points or fewer points.

Maine highlights: Things to do near Kennebunkport

If your hotel, flights and rental car are covered using points and miles, you can spend money on other expenses, like food and shopping. At least, that is my travel philosophy.

However, food prices in the area were a bit high, at least for this budget-focused traveler. Don’t be surprised if you find yourself paying upward of $34 for one lobster roll or $17 for six chicken wings. I can report that it was all delicious, and the lobster roll, particularly at Footbridge Lobster, was unmatched.

Luckily, even if you want to splurge on food in the affluent area, there are many free things visitors can do.

While in Kennebunkport, walk around the downtown area and visit the neighborhood shops. Visit the local beaches, such as Goose Rocks Beach and drive to the scenic Walker’s Point Estate. Take a 25-minute drive to Ogunquit and walk the famous Marginal Way, a 1 1/2-mile path along the coast and/or visit Ogunquit’s beaches.

Though Ogunquit also has many shops and restaurants, one major highlight was the Heritage Museum, where people can learn about the town’s history and its people through artifacts and pictures.

For nature lovers, take a walk through the Rachel Carson National Wildlife Refuge. For those leaf-peeping travelers, this would be a great way to see the fall foliage.

Related: ‘Bleisure’ travel: How I used points and miles to turn a business trip into a (nearly) free vacation

If you’re a foodie and want to invest your money in more diverse meals, drive 30 minutes to Portland, the state’s largest city, and hit the popular local dining haunts. A few personal favorites: Crispy Gai, Salt Yard, Mr. Tuna and Bread & Friends.

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TPG tip: When dining out, make sure you use a credit card that earns bonus rewards on restaurants worldwide.

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When driving around Maine, you’ll also notice a ton of antique shops, book stores, vintage clothing boutiques and, my personal favorite, coffee shops.

Overall, coastal Maine has much to offer, and the price points of these beach towns shouldn’t deter budget-friendly travelers from visiting. Utilizing rewards can help save you thousands of dollars when planning a long-weekend getaway to these affluent, charming seaside towns.