Kennebunkport is one of Maine’s most well-known summer getaways. The area is home to Victorian architecture centered around a quaint downtown area that’s highly walkable and picturesque.
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The port town also offers rugged views of the Atlantic, plenty of fresh seafood any time of year, and a maritime culture that beach-lovers appreciate. In summer, the area transforms into one of the country’s most scenic, family-friendly getaways. (One that comes with a hefty price tag to match.)
Despite its association as a charming coastal getaway, Kennebunkport is a steal to visit during autumn. Temperatures drop—along with prices. Many of the town’s picture-worthy cottages are available for rent during this time, when the crisp autumn weather ushers in pumpkin picking, spiced latte-drinking, and more.
It’s the perfect time to sink into the coastal magic while saving a few dollars. If you’re looking for a quaint place to stay, start with these cottage-core Vrbos in Kennebunkport, Maine.
[This article is part of TravelAwaits new Airbnb and Vrbo recommendation series. We dig into listings to identify the crème de la crème of Guest Favorites, Superhost listings, and hidden gems to make finding the perfect rental for your next trip a breeze.]
Top cottage Vrbos in Kennebunkport: at a glance
- Best waterfront cottage: Minnow Cottage
- Oldest historic stay: Historic Kennebunkport Home
- Most walkable: The Mary Jane
- A secluded hideaway: Cozy Beach Cottage
- Best for couples: Waterfront Cottage
- Best for families: 4 Briarwood
- Most spacious pick: Modern Victorian Luxury
- Luxury pick: The School Street House
Best cottage-core Vrbos in Kennebunkport, Maine
Minnow Cottage
Let’s kick off this list with one of the most impressive Vrbos in Kennebunkport: a luxury waterfront escape. The home comes with ocean and marina views from most rooms, along with a backyard with Adirondack chairs steps from the water. The location puts you in the heart of Dock Square, meaning you can also walk to many of the town’s top shops, restaurants, and cafes. Despite its cozy size, this is a three-bedroom where you can sleep six guests.
Historic Kennebunkport Home (Aaron Hovey House)
Many Vrbos, including The Mary Jane (below), are historic and date back to the 19th century. However, this is one of the older rentals available. The home dates back to 1797 and was recently added to the National Register of Historic Places. The home comes with three bedrooms and plenty of historic features that give the space a warm, cozy feel. As a perk, you’re also right in the village center just steps from Dock Square.
The Mary Jane
The Mary Jane dates back to 1850. The interior has been carefully maintained to preserve its historic features, then refurbished with more modern sensibilities. You’ve got a fantastic balance between Old World Charm and comfort. The added perk at this Vrbo is its location. You can walk to Dock Square and the village center in less than ten minutes, or head the other way to relax along the Kennebunk River.
Cozy Beach Cottage
One of the best parts about visiting Kennebunkport is its walkability. But if you want to venture a little further off the beaten path to capitalize on your downtime during the autumn season, here’s your top pick. This one-bedroom home is in a quiet neighborhood that offers a waterfront escape where you can listen to the waves lap against the shore in tranquility, just a few steps from the door. The outdoor patio also gives you a place to soak up your solitude without any noise pollution.
Waterfront Cottage
The one-bedroom listed above is a great pick for couples—but this oceanfront cottage can’t be topped for couples who want some quality downtime. The home comes with direct ocean views that overlook a nearby lighthouse, along with a fireplace inside for extra-cozy evenings. If you like to get out on the water, you can also bring your own kayak, floaties, or canoes, as this rental comes with dock access.
4 Briarwood
If you’re visiting Kennebunkport with family, this three-bedroom home gives you a fantastic space for cooking meals, dining together, and otherwise hanging out. The two-floor historic home comes with three large bedrooms, one of which comes with a crib and another has two twins and a queen bed. There’s also a large yard out back, with a patio, grill, and play area. Plus, you can walk into town from this Vrbo, letting you park the car and leave the keys behind for a few days.
Modern Victorian Luxury
The rental listed above, 4 Briarwood, gives you all the space you’ll need as a family—but if you want a truly roomy rental, start here. This massive 1908 Victorian home has five bedrooms that can sleep groups of up to thirteen. It’s got all the features you’ll need for a group that size, too, like functional and comfortable bedrooms and a solid washer-dryer combo. There are other amenities you’ll enjoy, like the wraparound porch with rocking chairs and a beach equipment setup that you can use into the fall season.
The School Street House
Step into a designer’s dream house at this three-bedroom Dock Square home. The 1820 schoolhouse has been converted into a luxury stay with a chef’s kitchen, outdoor living spaces, and upscale perks like Aesop products and Italian linens. You’ll feel like you’re staying in a fully private boutique hotel.
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