If you’re vacationing in Cape Cod, expect a balanced trip.
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The area is home to some of the country’s most richly historic coastlines and small towns. There are sprawling beaches, quaint villages, and a laidback vibe that you’ll feel the second your toes hit the sand. It’s the type of place where you can disappear, whether via train, hiking path, or beach.
In fact, celebrities and other bigwigs still return to Cape Cod. It’s the type of place that hasn’t lost its luster since its heyday as a vacation spot for wealthy city-slickers. To this day, it’s the type of place where ordinary life becomes the setting for extraordinarily relaxing vacations.
And while you can find lovely boutiques across Cape Cod, I recommend setting yourself up like a local for your visit. To do that, you’ll need a solid private rental. Not just any private rental, but one that touches on the history and charm that the area is known for. A little cottage-core, anyone?
Here’s where to start if you’re interested in finding cottage Airbnbs in Cape Cod with historic flair.
Start with these 3 cottage Airbnbs on Cape Cod
- Unbeatable beachfront: Beach House Bungalow (Barnstable)
- Small town perfection: Cozy Home Close to Town (Plymouth)
- A more modern take: Chit Chat Cottage (Chatham)
11 cozy cottage Airbnbs on Cape Cod with historic flair
Cozy Home Close to Town (Plymouth)
This lovely two-bedroom cottage sleeps four in two upstairs bedrooms. Downstairs, you’ve got a quaint living room, plus a patio to enjoy and a fire pit nearby. The main perk is the close proximity to downtown Plymouth, which you can reach on foot in just ten minutes. You also have scenic hiking trails available across the street.
Sweet + Sunny Cottage (Plymouth)
This two-bedroom cottage offers comfort, a great location, and updated features. The kitchen is fully equipped, while the bedding is top-notch. (There are even blackout curtains for any troubled sleepers.) You’re only a five-minute walk from White Horse Beach and Priscilla Beach. The property also has an outdoor shower so you can rinse off easily in summer.
Owl’s Nest Cottage (Eastham)
Tucked away under greenery, this one-bedroom is full of rustic finishes and historic elements—including a wood-burning fireplace. It has hidden garden vibes, giving you a scenic resting place. Nearby, you have some of Cape Cod’s top beaches, including Nauset and First Encounter, along with Nickerson State Park.
Lil Rose (Provincetown)
This cozy two-bedroom sleeps up to five with a twin bed option, making it great for families with small kids. You’ve got a solid balance between small-town vibes thanks to the short distance to Provincetown, along with proximity to major beaches. Just know that this rental has minimum stay requirements depending on the season. You might need to stay a whole week in summer, for example.
Provincetown Beach Cottage (Provincetown)
Speaking of Provincetown, this is a one-bedroom cottage with a grand feeling and a fresh nautical décor. You’ll feel like New England royalty with a white picket fence and a private walkway straight to the beach in the popular West End neighborhood, which you can see from the living room. This cottage is one of eight units that are part of the Delft Haven complex.
Cape Cod Cottage by the Bay (Dennis)
If you’re looking for a classic cottage full of historic wood features, look no further. This rustic-but-classic cottage has cathedral ceilings, wide plank floors, and other handcrafted features. Just know that this is a family cottage that isn’t a full-time Airbnb. It doesn’t have AC, but all 15 windows open. Think: A cottage that takes you to the Cape Cod of yore.
Dune Haven Cottage (North Truro)
Though fairly average on the outside, this cottage is a shabby-chic haven on the inside. The property dates back to the 1950s, giving you private beach access to Cape Cod Bay. You also have solid views of Provincetown in the distance. As the host describes, this place is like a living art installation. Uniquely, it comes with a ‘rest and renewal’ retreat option that involves guided meditations, forest bathing, and more, which is provided by the host.
Beach House Bungalow (Barnstable)
This beach house is located on a large family estate, meaning you’re renting a guesthouse. It’s a one-bedroom, two-bathroom cabin-style setup that comes with a private beach and a boat ramp. There’s also an outdoor shower. The real perk is the solitude that you’ll feel. You won’t run into the family while you stay here, making it a private retreat.
Rum Runner’s Shack (Wellfleet)
Located in the heart of Wellfleet, this lovely cottage puts you within walking distance of major beaches, along with hotspots in town. That includes taverns, restaurants, and shops. Just know that, while this is a two-bedroom that sleeps four, only two adults are permitted per stay. Kids are welcome. From June through September, there’s also a seven-day minimum on rentals.
Petite & Sweet 1920s Cottage (Chatham)
This lovely cottage, which dates back to the 1920s, has two bedrooms and one bathroom that can comfortably sleep four. Despite the property’s age, it has air conditioning and heating, along with a newly renovated bathroom. As a perk, you’re located steps away from a shared waterfront area. No pets are allowed at this rental due to HOA rules.
Chit Chat Cottage (Chatham)
This two-bedroom, one-bathroom cottage was built back in the 1920s. Since then, it’s been beautifully restored to blend both historic and modern features. Fantastic and sunny interior aside, the rental is located in a prime spot in Chatham. You’re less than ten minutes drive from popular beaches, and only steps away from the lovely White Pond where you swim.
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