Such a simple phrase, yet such a depth of memory and meaning. The following three homes are great examples of the peace and serenity that can be found in the region, as people try to get a bit of respite.

Everyone’s connection to a home on the Cape arrives from a different, yet similar route. Some of us vacationed here as a family and look to re-create that experience for our own families. Some have chosen to put down roots after a life of hard work and diligence. Some are just beginning their path of discovery with the region and might be reserving one precious week in the summer or shoulder season—a chance to literally get away.

Whatever the reason, however the connection was established, time on the Cape, with friends or family, takes on a set of memories that are painted in hues of happiness, laughter and connection. 

For the past few years, as we round the cusp into the warm, gentle season of summer, we have explored the options available in the rental market on the Cape and Islands. We are fortunate to have such a wide-ranging selection of homes that provide sanctuary, and a backdrop for kinship, all while taking advantage of this special landscape. This year, perhaps more than ever, the need for an escape while balancing the needs and concerns for others is paramount.  The properties on the following pages allow for memorable time to gather together while still maintaining a sense of privacy and protection. -Julie Craven Wagner

Quintessential Cape

By Julie Craven Wagner · Photography courtesy of Robert Paul Properties

For Keenan Flynn, what makes up a quintessential Cape Cod rental property is an understanding that is deeply ingrained in his body, mind and soul. Flynn, who grew up in Cotuit and spent childhood summers racing down to the docks of the iconic Mosquito Yacht Club and riding his bike in a quiet village atmosphere that is repeated up and down the region, knows what a summer experience on the Cape is all about. Today, he is member of the Robert Paul Real Estate team, representing both buyers and sellers, and considers himself fortunate to be able to raise his own family in Cotuit. After all, how many of us can claim that our children are growing up the way we did?

But, being a landlord was not forefront in Flynn’s life plans. A visit to a college friend’s new summer home in Edgartown planted the seed. “I asked them, ‘how did you manage to get such a great home?’” Flynn explains. “They said, ‘Well, we come for six weeks of the year, and we rent it the rest of the time. That covers all of the expenses.’ Suddenly, I started to look at real estate differently.” Flynn, who at the time was not in the real estate business, set about analyzing which parts of the Cape were in premium demand for high-quality seasonal rentals. His research concluded that the communities of Chatham and Osterville were the preferred destinations for the kind of properties that interested him; Osterville was a natural choice due to his proximity in neighboring Cotuit. 

31 Parker Road came on the market at just the right time. The previous owners had outgrown their beloved Cape getaway, and the timing was right for both parties. The sellers  were looking to up-size, and Flynn was ready to enter the market. “The previous owners were meticulous when it came to maintenance on the home, and I have followed suit,” Flynn says about making the property truly turnkey. “So, to get the house ready for the upcoming season, all we had to do was decorate and stock it.” 

This summer will be the third season that Flynn has welcomed renters, who have become more like extended family, into his charming Cape cottage. “We have been lucky that a portion of our tenants have become repeat clients,” Flynn explains. “And they not only have deliberately chosen their preferred weeks, but in some cases, extended the duration of their booking.” For anyone who visits the property, that does not come as a surprise. The home, which is a short stroll to everything the village of Osterville has to offer, is that type of Cape Cod cottage that could show up on the silver screen. A picket fence with a cottage garden in full bloom greets visitors and passersby with a casual charm that encourages a stop for a whiff of roses and daylilies. White clapboard on the exterior is brought to life by an aqua painted front door crowned with a seaside wreath that whispers, “Come on in, and maybe stay awhile.” 

Inside, the cottage charm is evident by the freshly painted white, mid-century paneling and convenient built-ins throughout. Neat and tailored comfortable furniture, in coastal hues of blue and white, pull together a spacious seating area in the living room with a focus on a warm fireplace. This is not one of those typical summer rentals cobbled together with a collection of furnishing sourced from the attic and local second-hand shops. Instead, attention to detail with a focus on a cohesive and thoughtful design is apparent at every turn. Bedrooms are freshly made with crisp Boll and Branch linens, while wool needlepoint throw rugs provide comfort as they grace beautifully stained hardwood floors. The four bathrooms are modern and pristine and allow enough privacy for everyone in the four-bedroom house. But, the charming interior of a time gone by is not the only appeal of this getaway.

The backyard and outdoor spaces are simply unexpected in such an idyllic presentation. Outside, among a lush and maintenance-free landscape, a mesmerizing waterfall splashes into an in-ground pool, with a swim-up bar that offers an oasis for a fun-filled retreat. A fully functional outdoor kitchen services the bar that has seating both in the pool and out, allowing those that prefer to stay dry or wet for their summer vacation to indulge in either. A dining area is perched above the pool in the shade for family dinners. Additionally under cover, in the adjacent pool cabana, a comfortable sectional wraps around another bar capped by a large screen television. For those seeking a mega-dose of vitamin D and perhaps a golden-hue to their skin, sturdy and comfortable padded chaise loungers stand at the ready on the surrounding stone pool decking. A collection of comfortable seating surrounds a spacious fire pit, providing the perfect place to unwind and connect during the cool evenings.

Flynn has chosen Michelle Sylvia with Robert Paul Properties to represent and handle all of the business associated with his unique property. “If I could make any suggestion to anyone considering an investment property, it would be to use a realtor,” Flynn shares. “I was not in the real estate business when I took this on, so I can speak from both sides without bias. But to have a professional that is responsible for all aspects of this property means not only that I have peace of mind, but, I believe, that I am a better neighbor to the abutters and the village as well.” Flynn touches on an important point that is perhaps not considered as deeply for other investment homeowners. With a third party handling the responsibility of the myriad of considerations involved in the business of seasonal rental property, the headaches and reputation of the individual homeowner are far less at risk.

On that fateful ferry ride to the Vineyard, to connect with his college friend, Keenan Flynn might never have expected that his future would be instrumental in creating a space for memories and meaningful respite for complete strangers, but in fact, he is providing a home for those who are in search of just that.

This property can be found at robertpaul.com or by contacting Michelle Sylvia at michelle@robertpaul.com or Keenan Flynn directly at kflynn@robertpaul.com 

The View is Better from Up Top

Like the lively streets of Provincetown, this home is overflowing with personality, charm, and world-class views. 

By Allyson Plessner · Photography courtesy of Del Mar Marketing

It’s true what they say: The view is better from up top. Take this Provincetown home, for example. From its vantage point atop Telegraph Hill, overlooking the very tip of Cape Cod on one side and Cape Cod Bay and beyond toward the gorgeous Boston skyline on the other, this property enjoys panoramic ocean views. With Provincetown Harbor and its famed beaches below, what more could you want from a Cape Cod getaway?

“This home is perfectly situated to be high above all the hustle and bustle of Provincetown while still being able to see every single detail of the historic area,” says Luke Chapman, owner of Del Mar Vacations. “It’s the perfect property for social distancing,” he expands, referring to actions taken in recent months to slow the spread of global coronavirus. But, when the world is no longer banding together to stay home in an effort to avoid overwhelming the healthcare system (especially on the small spit of land that is Cape Cod), and instead banding together to appreciate small, treasured moments like a day at the beach in Provincetown, this property becomes the ideal rental home for the very same reason that Chapman makes his observation: it is private and serene while still being close to all the action.

Inside, the home boasts a state-of-the-art kitchen, perfect for preparing a meal or a morning cup of coffee to enjoy on the wrap-around porch as the sun sends glittering rays over the tip of Provincetown and Long Point Light in the distance. The ambiance is all about relaxation, with a spacious master bedroom and master bath on the second floor, complete with a soaking tub. Multiple guest rooms, guest baths and a convenient washer and dryer make this the perfect location to gather with family and friends. From drying off after a long beach day on one of three outdoor decks to curling up by the fireplace with a good book and maybe a frosty drink, this space leaves nothing to be desired. And, what vacation retreat would be complete without a hot tub?

“The multi-levels of this home give it a lot of depth. There are three decks, and the whole space flows really well between the indoor and outdoor areas which all connect,” explains Chapman, noting the expansive back deck and large lawn space. He even points out a private dog run that means the family pet doesn’t have to miss out on the Cape Cod vacation! “Add to that the incredible architecture that allows for a water view that can be seen from all sides of the home—just about 270 degrees of stunning scenery—and this home is definitely a touch above the rest,” expands Chapman.

As a full service property management company that also specializes in guest services, Del Mar Vacations is uniquely positioned to provide the best possible experience at the best possible locations. Like this Provincetown home, all of Del Mar’s properties are handpicked to be the finest representations of the incredible vacation experience that Cape Cod is famous for. For homeowners, Del Mar practically guarantees rental income while also taking care of a client’s beloved space. From cleaning, lawn care, and waste removal, to reservation management and hands-on customer service, Del Mar simplifies the rental process for both sides of the agreement, setting the standard on Cape Cod for superb vacation experiences. “Del Mar Vacations provides hotel quality hospitality and property management services,” explains Chapman. “We are here to make sure guests have a great vacation, and homeowners don’t have to lift a finger.”

“With this home, the owners are really great partners for Del Mar,” continues Chapman. “They are also longtime business owners and amazing supporters of the local Provincetown community. And, of course, their property is just exceptional. Those things are exactly the types of qualities that we look for when building meaningful relationships with our clients.” Del Mar’s award-winning photography and dedicated marketing strategies certainly do the home justice as well, and serve to highlight Chapman’s favorite element: the natural lighting. 

“There are windows and skylights everywhere in this home,” enthuses Chapman. “It’s stunning, and the orientation is such that there are no neighboring homes visible from any of the major living spaces, so it feels very private and peaceful.” 

Eye-catching original artwork hangs on the walls throughout the home, tying each of the rooms together with a sophisticated, nautical flare. Clean white countertops, soft wall colors that seem to switch between light gray and calming, sea foam blue in the light, and vibrant pops of color like canary yellow lounge chairs give the home a personality all its own. It’s coastal, laid-back and fun, while still, in many ways, feeling chic and refined, much like the famed town it overlooks. Like Provincetown, this home is an escape all its own—one where guests are sure to feel special, relaxed, and above all, welcome.

“We are in the business of providing experiences,” says Chapman. “We don’t want to give guests simply an empty vestibule, and this home, with its many unique and expansive views, its striking architectural detailing, the original art, and inspired amenities, is an experience unto itself.”  

This property, “Birds Eye View,” can be found by visiting book.thisisdelmar.com. Any of Del Mar’s amazing customer service team members are ready to assist.

The Capacious Compound

This luxurious Orleans property is perfect for a multi-family vacation, with a range of spaces for the group to gather both indoors and out.

By Brenna Collins · Photography courtesy of Pretty Picky Properties

A Cape Cod vacation attracts New Englanders and globetrotters alike. For those who visited these shores as a child, the Cape continues to emblematize carefree memories where time seemed to stand still. For newcomers, the Cape’s culture paints pictures of idyllic days in the sand, local seafood delights, and a chance for blissful relaxation. Regardless, choosing a town for your stay all depends on your wish list. Preferences like the waves of the National Seashore versus the quiet of the bayside, or the bustle of a downtown versus an off-the-grid oasis, all impact a rental choice. When it comes to the home itself, today’s premier properties offer growing lists of amenities. Pretty Picky Properties, Cape Cod’s only select vacation rentals specialist, has a plethora of fabulous homes to choose from scattered across the Cape. One in particular, nestled just a mile from the famed Nauset Beach, emits an impressive aura of a resort-style, private family getaway. The home is just a short walk away from the village of  East Orleans, where several restaurants, a gourmet market, and ice cream parlor await, as well as a marina for boat rentals and tours. Orleans offers an eclectic mix of culture, with its shops, galleries, restaurants, and both bayside and Atlantic beaches. This luxurious home is the perfect backdrop for a carefree vacation, with so much to offer that you may never want to leave its grounds.

Arriving on its perfectly groomed, stunning property, excitement about all your vacation may hold will immediately kick in. Stepping through the front door, a spacious, open-concept floor plan has multiple distinct gathering areas while seamlessly flowing as one large space. A white and neutral palette predominates in the home, establishing a bright and calm coastal vibe. The range of windows provide ample natural light, letting in sunshine and enhancing the simple, clean color palette. The home has five bedrooms, five and a half bathrooms, and can sleep upward of twelve guests.

As the heart of the home, the fully outfitted chef’s kitchen is key, allowing your whole party to gather. The large island, topped with a gorgeous white granite, adds plenty of extra storage as well as a space to enjoy light bites. The top-notch stainless steel appliances are perfect for dining at home amidst your vacation. Adding a modern touch, a gray tile backsplash accents the walls of the stove and sink. Blending in with the surrounding clean, white tones, the refrigerator is covered with the kitchen’s corresponding white cabinetry. With its space and amenities, this kitchen is equipped for a five-star meal. 

A few steps away, the living room is effortlessly adorned with comfortable couches, chairs and a patterned rug to create a distinctive space. A shift in ceiling height further distinguishes the room, with higher vaulted ceilings dramatically enlarging the area. Complete with a fireplace and mounted television, the living area is waiting for game and movie nights.

Over in the dining room, the transition back to a lower ceiling helps to create a more formal, yet cozy environment. A seating area and wet bar adds charm, maximizing space and perfect for a quiet cocktail. Next to the dining table, a long stone fireplace creates a charming statement.

Complete with two first floor master bedrooms, the home is fully functional for a multi-family getaway. The first master bedroom has a more nautical feel, with an accent wall, bedspread, area rug, and décor pieces in navy blues. This spacious room is a private getaway in itself, with a full bath, fireplace, cozy seating area, and doors leading to the deck outside. The second master is keeping with the home’s predominant white, coastal theme while combining natural and modern accents. With a fireplace and mounted television, a full luxury bathroom, and private balcony, this is an equally luxurious option.

Upstairs, the three additional large bedrooms are tasteful and spacious. The third bedroom incorporates a light blue, beach theme, mixing colors illustrative of the sand and sea. This large space is equipped with a queen and twin bed, a convertible full sofa, and a private bath. Down the hall, the fourth bedroom is similarly set with a queen and twin bed, convertible full sofa and full bath, and beautifully combines whites and blues.

An exciting hideaway like no other, the bunk room can house the remaining guests. Two bunk beds offer a twin on top and a full bed below. Additionally, three twin beds line the vaulted wall for even more sleeping space. Attached to the bunk room is a cozy game area with a jumble of bean bags, as well as a full bath.

While the home’s interior may be exquisite, the true entertainment lies outdoors. A backyard oasis awaits just beyond the porch, with a pool and cabana. The 18×40 heated, salt water pool is the star of the show, flanked by a hot tub, outdoor dining table, and outdoor grill and kitchen area to cook up some summertime cuisine. To prolong your summer nights, the fire pit with surrounding seating is a peaceful amenity to connect and unwind.

Inside the cabana, the home’s aesthetic extends into this bright and cozy escape. A seating area, big screen TV, gas fireplace, and full bar create an indoor haven amidst the outdoor fun. For extra relaxation, the sauna sits just beyond the main area. Other amenities include a basketball court, yoga studio, and yard play area.

Pretty Picky Properties highly recommends this luxury family compound, noting, “larger guest groups cherish the property for its high-end features, furnishings and finish throughout.” Pretty Picky Properties manages more than 150 private homes for summer vacation rentals, ranging from Barnstable to Eastham. In 2003, Jim and Karen Decker founded Pretty Picky Properties due to an untapped need in the market. As rental property owners in Brewster with years of management and business experience, the Deckers knew the kind of service the local rental home industry needed, yet was lacking in their opinion. Today, discerning vacationers visit prettypicky.com for the Cape’s leading portfolio of premier summer rentals, each distinguished for its extraordinary location, quality accommodations, or both. In keeping with the same values that initially inspired the company, Pretty Picky’s high-touch service includes trained detailers who execute an exclusive “Property Prep Punch List” on site as the property prepares for turnover day, as well as personally greeting arriving guests. Additionally, the partnership of Pretty Picky and Monomoy Real Estate and Construction provides a single, dependable source for real estate market intelligence and leading edge builder know-how—as well as unparalleled select vacation rental expertise. Pretty Picky has offices in Brewster, Chatham, and Orleans, offering their services to a wide range of Cape Codders.

A home like this Orleans compound makes clear the possibilities and quality choices available when searching for the perfect rental. Whether it be the grandiose pool area or the expansive chef’s kitchen, this home has a space fit for every guest. With an option this luxurious, your vacation could simply consist of quality time with loved ones in the private, resort-style beauty of the property itself. 

This property can be found at prettypicky.com or by contacting Blake Decker at blake@prettypicky.com

For more places to stay, check out our 2019 Best Of Lodging winners here!