Each journey to renting a home on the Cape is based on its own unique purpose, although pieces of the path are the same. For some, it’s about revisiting cherished memories made with family in the past and wanting to share that same experience with their own loved ones. Others have decided to make the trek and explore the place that they’ve heard has so much natural beauty and history to offer. And there are those who are seeking a scenic and special place to commemorate an event that will forever etched on their hearts like an engagement, a wedding or a family reunion. We think these three distinctive properties represent the best that Cape Cod has to offer—whatever your intention is to visit—and that they’ll be a part of the memories that pull at you to return again.

One golden afternoon, two friends sat on the deck, savoring the gentle breeze as the soft hum of the radio filled the air. Then, as if on cue, Summer Wind by Frank Sinatra drifted through. “The summer wind came blowin’ in from across the sea.” It was as though Sinatra had penned those words with this very place in mind—a breathtaking waterfront retreat, where the salty air and endless ocean views seemed to create the perfect backdrop for timeless summer days. And so, the home was christened on the spot with the fitting name, Summer Winds. 

Nestled along the beach in the picturesque town of Barnstable, 111 Long Beach Road has a quintessentially coastal New England look, with its gray cedar shingles, crisp white trim and traditional dormers—a perfect picture of a classic Cape Cod home. A charming cobalt blue door invites you into this luxurious property and gives the initial hint of the color that is the predominant hue throughout, and echoes the natural beauty of Nantucket Sound just steps beyond.  

This home makes for the perfect coastal getaway; for while the Cape is full of fabulous restaurants, family-friendly activities, natural beauty and recreation, chances are you may not want to venture from this spot once you arrive. And why would you, with its prime location just steps away from serene Long Beach, 6 bedrooms, 5 bathrooms and plenty of space for family or friends to enjoy this unparalleled waterfront experience. The property boasts spacious living areas, elegant interior design that reflects a casual seaside theme, and expansive outdoor spaces that are perfect for hosting gatherings or simply enjoying the breathtaking views—day or night. 

There are two separate dwellings on the property; the main home and a detached cottage above the two-car garage. Michelle Sylvia of Berkshire Hathaway/Robert Paul Properties shares that the property has direct access to the private beach as well as a seating area with a firepit and perhaps even better, depending on who you ask, is the walkable distance to the area’s iconic Four Seas Ice Cream. 

Renters both young and old will be drawn to the private hot tub situated on the outside lawn where, by day you can soak after a dip in the ocean or by night, sit under the stars. A stone fire pit adds to the property’s relaxed coastal vibes, creating the perfect gathering spot to talk, plan, or share a laugh together. 

Additional perks include high-end luxury linens and furnishings chosen by a talented interior designer and full concierge service from Sylvia herself. Whether you’re looking to unwind at the beach or explore all that the Cape has to offer, the attention to detail found at Summer Winds offers both comfort and style—the best of Cape Cod living. 

To see a complete video of the property and inquire about its availability, as well as view her other elite properties, visit Michelle Sylvia’s page through Berkshire Hathaway at irentcapecod.com.

Photos by Bryan Stearns

The Port at 177 Fox Hill Road in the charming town of Chatham is a dreamy escape set on 1.6 acres and feels like a page plucked from history—where if the house and its grounds could speak, they would whisper tales of the residents and visitors of generations past, each with a story replete in the magic of Cape Cod.

Blake Decker, CEO of Pretty Picky Properties explains that The Port has a rich heritage that enhances its charm. Originally constructed as a family estate, the property was carefully designed to blend seamlessly with its naturally beautiful surroundings. “The current structure was built circa 1800 by the descendants of William Nickerson, the original European settlers of Chatham. This area was home to many of the earliest successful shipping merchants and featured some of the earliest anchorages in what is now Pleasant Bay, Crow’s Pond and Ryder’s Cove. Hence, The Port was deemed an appropriate appellation,” Decker shares. 

Still today, Chatham is known for its charming downtown and pristine beaches, making it a sought-after Cape destination for visitors. Decker notes that whether you’re looking to explore the Cape Cod Rail Trail, take a scenic boat tour or fishing charter out of nearby Ryder’s Cove, or enjoy boutique shopping and dining, The Port provides an ideal base for all of these activities to enjoy with family or friends. 

With luxurious amenities like a heated pool, a fully equipped gourmet kitchen, spacious living and dining areas with comfortable seating and large windows that offer spectacular views of the grounds and a nearby golf course, The Port has a “something for everyone” appeal that will satisfy most guests. Over the years, the estate has been thoughtfully maintained and renovated to preserve its classic Cape Cod appeal while introducing modern comforts. 

With 8 bedrooms and 7.5 bathrooms, “The Port” can easily accommodate up to 18 people comfortably, giving you the space to spread out or come together. The property’s history adds to the overall luxury, making it more than just a vacation rental—it offers guests a chance to experience a piece of Chatham’s legacy, and be surrounded by the natural beauty of the Cape. Decker says, “It feels like a coastal English garden with Cape Cod charm in a grand estate setting.” 

One of the property’s greatest assets is its outdoor spaces: the expansive heated pool and pavilion offer the perfect alternative when a beach day isn’t on the agenda, or they can even provide a refreshing spot for a post-beach dip. The firepit surrounded by classic Adirondack chairs is a fun spot for gathering around and the outdoor shower is a seasonal Cape Cod favored by so many. In addition, there is a spacious outdoor covered seating and/or dining area, complete with comfortable seating, which provides the perfect setting to enjoy meals al fresco while staying sheltered from the elements, which are often unpredictable on Cape Cod!

Original wood beams and rafters soar in the large barn-turned-guesthouse. Decker says, “It’s such a unique space, ideal for dinners or gatherings.” The barn is a true gem and standout feature of the property at 177 Fox Hill and creates a sense of openness and rustic elegance. 

Stellar reviews from former guests reflect that whether you’re looking to unwind in a peaceful setting, explore the best of Cape Cod, or spend a memorable vacation with ones you love, The Port will be the perfect backdrop for your unforgettable time. 

To see this estate and other outstanding rental properties in greater detail, head to prettypicky.com. 

Photos by Ed Glick at Bluwater Photography

Larkspur Cottage in North Truro isn’t just a place to stay—it’s a state of mind. This charming beachfront rental may be a modest 450 square feet—significantly smaller than many of the expansive properties featured here—but what it lacks in size, it more than compensates for with the unforgettable experience of staying right by the sea. Guests rave that staying at Larkspur is almost like being aboard your own private cruise ship, with panoramic views out of windows that offer unobstructed scenes of the ocean in all its glory. 

Larkspur is regarded as a landmark and is one of the 22 historic Days’ Cottages. While the exterior of these cottages cannot be modified, each is truly unique on the inside. Owner Daniela Ortiz Bahamonde takes great pride in ownership of Larkspur and it shows in every detail, from the space-efficient design, comfortable furnishings and specially curated décor accents. “We chose beautiful teal appliances that bring a happy pop of color in the kitchen. Setting the table is such a joy as we have carefully assembled dinnerware and utensils fit for a beach house,” she shares. The stark white canvas of the home was a deliberate choice, as Ortiz Bahamonde wanted the natural palette to be the focal point. She says, “The shades of the water and beach take center stage and allow for golden hour to be welcomed inside the cottage through the wall of windows. The vibrant hues of orange and yellow splash inside and completely transform the cottage, making you feel as if you are a part of the sunset.” Adirondack chairs are perched on the sand facing the ocean, inviting guests to sit and gaze out at the horizon where, if you are patient—and lucky—you may see whales splash and breach in the distance. Seals are common visitors as well in the sometimes tranquil, sometimes choppy waters. The cottage’s design creates a serene and inviting backdrop, allowing guests to fully relax and appreciate the unique beauty of this part of North Truro.

Another distinct feature of the property is a shared boat ramp which allows guests to pull up their boats and launch them onsite, but if small craft recreation is more your speed, Larkspur provides 2 kayaks to borrow for local exploring. The public beach is steps away and is a perfect place for fishing off the small nearby pier. Ortiz Bahamonde adds, “Children can spend hours around the jetties searching for hermit crabs, shells and pretty rocks.” And to end your day on a perfect note, gather around a bonfire on the private beach, where you can toast marshmallows and make s’mores under the stars. If Cape Cod’s weather isn’t agreeable to enjoying the beach one day, nearby, and not to be missed is the Provincetown Public Library which features a full-size fishing schooner for both young and old to enjoy discovering. 

Ortiz Bahamonde offers stellar concierge-style customer service from the time of booking until the time of check-out. Whether you have questions, need guidance or assistance with anything from babysitting to delivery, she is available to ensure your stay at Larkspur is a memorable one. Your only problem may be getting accustomed to drifting off to sleep to the soothing rhythm of the waves, and awakening to the tranquil beauty of one of Cape Cod’s most breathtaking views. 

For amazing images and video of the property, as well as booking information, visit larkspurdayscottages.com or see their Instagram page @larkspur.dayscottages.

Photos by Stephanie Loda of R.E. Photography LLC