Dream Vacation Homes

For $10,000 to nearly $30,000 a week in the summer, you can live in the lap of luxury with your own private dock and beach, infinity pool and guest house, and ocean views from nearly every room.

By Vivian Siempos Haidas

Cape Cod is known more for cottages than mansions, but that doesn’t mean that dream homes don’t exist. Last year we featured tiny homes on Cape Cod, with the idea of learning to live with less. This year, we are bringing you to the other end of the spectrum by showcasing luxurious vacation homes.


Chatham has a picturesque shoreline and homes to match. It is home to a renowned wedding destination—Chatham Bars Inn—and historic Chatham Lighthouse. At Chatham Fish Pier, visitors can watch fishermen bring in their daily catch and also catch a glimpse of the local seal population that idly swim by waiting for their next meal. Chatham has everything that is quintessentially Cape Cod.


This Shore Road home with a warm and inviting vibe is every bit a luxury vacation rental. Its weathered wood shingles and rock columns speak to old Cape Cod and belie the beautiful and simply designed interior spaces painted in pale, earthy tones. A soaking tub and steam showers guarantee the ultimate relaxation. The private balcony and patio of this octagonal-shaped home offer places to sit and appreciate panoramic views of North Beach and Chatham Harbor or gaze out at the endless horizon and listen to the sound of the waves.

The beach is steps away, so it is possible to wake up and walk along the sandy shore, take a refreshing dip in the water and then dry off while watching the boats come and go from Chatham Harbor.


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This home offers more than just exceptional views, relative privacy and comfortable living quarters. It is located on the grounds of the Chatham Bars Inn, which means that guests have access to all the amenities of the inn, including the concierge and a car service, as well as a daily maid.


Shore Road
Type: Waterfront
Bedrooms: 3
Baths: 5 full, 2 half
Price: $27,000 per week




The home at 94 Horsefoot Path sits on one of the most coveted beaches on Cape Cod: Mayflower Beach in Dennis. On weekend mornings in the heat of the summer, a line of cars stretches a mile long as people attempt to get a parking space to enjoy the fine sand and cool, clear water at Mayflower Beach. The parking lot fills up by 9:30 a.m., and at high tide, the beach is so full of people that it’s hard to find a spot to put down a chair.

This home allows its guests to bypass the line and step out of their backyard onto a sandy path, surrounded by sea grass into their own private section of Mayflower. Guests can lie back and observe the tide as it rises and recedes and take a long walk on the shore.

The design of the home brings the outside in, with colors that mimic the beach—soft blues, greens, creams and tans. The open-concept first floor allows guests in the kitchen, dining room and sitting room to interact and have the same extensive view.

The large patio feels at one with the sand dunes. Guests can lounge on a massive outdoor couch after a day at the beach and enjoy the transformation of the sky as the sun sets. Here, close to the ocean, guests can be lulled to sleep by waves gently breaking on the shore. In the morning, gentle ocean breezes refresh you—there’s no need to nab a parking space so relax and admire the view or stroll onto the beach when the desire strikes.


94 Horsefoot Path
Type: Waterfront
Bedrooms: 4
Baths: 4 full, 1 half
Price: $10,000 to $20,000 per week



78PopponessetIsland116Popponesset Island in Mashpee is another exclusive area of the Cape. It lies in Popponesset Bay and is separated from the mainland by Popponesset Creek.

“With just 60 homes on a quiet tree-lined street, you feel like you are a million miles away from civilization,” says Mindy Wachtenheim who with her husband, Stanley, owns 78 Popponesset Island Road, a beautiful home lined with windows overlooking the bay. In the horizon, you can watch the ferries going back and forth from Martha’s Vineyard.

“We loved the view of Popponesset Bay and Nantucket Sound. With magnificent, wide expansive ocean views as well as busy boating vistas, this is as good as it gets,” says Wachtenheim, explaining how she and her husband settled on this particular location.

78 Popponesset Aerials (2)


They tore down the 1960s ranch house and built what was, in 1993, the largest home on the island. There is a pool and a hot tub, as well as a pool house that doubles as a guest house overlooking the ocean. In addition, you can enjoy your own small sandy beach and a dock, making it a dream setting for a Cape Cod vacation.

“This home offers the opportunity to make summer memories with people from all over the country. The location has great restaurants, golf, tennis, beach clubs and access to all that Cape Cod has to offer,” says Wachtenheim.

*If you’re lucky, you may catch a glimpse of New England Patriots owner Robert Kraft, who has a home on the island.


78 Popponesset Island Road
Type: Waterfront
Bedrooms: 6
Baths: 5 full, 2 half
Price: $15,500 per week



Oyster Harbors is an island and private, gated community within the village of Osterville. The homes in Oyster Harbors are the epitome of Cape Cod luxury. The tree-lined streets lead to stunning estates, surrounded by acres of untouched land. Vacationing on Oyster Harbors allows guests to enjoy the peace and quiet of this quaint island, but they can also easily drive over the bridge and venture onto the mainland.

With its stucco and rock façade, the property at 25 Oyster Way looks more like a chateau in France than a vacation rental on Cape Cod. The gardens in the backyard are similar to what you’d expect at a castle, only on a smaller scale. It is a place where you can while away the hours with only your thoughts and the sound of the surf.

The recently remodeled interior is primarily white with pops of color in each room. Walking through the house is a titillating experience of design, with each room having its own personality. There are multiple sitting rooms, but the one that stands out is the massive great room with vaulted ceilings and columns made from pecky cypress. It is an open room with a row of French doors that allows everyone to have a view from wherever they are sitting.

OysterWay_045-2821133The dining room, featuring floor-to-ceiling windows, is more than just a place to eat, it’s where one can sit and admire the view. The kitchen is large and has an eat-in bar, so cooking and socializing can happen simultaneously. The home not only has a water view, but also has a dock—perfect for those who enjoy water sports like paddleboarding and kayaking. There is also ping-pong and a fire pit to gather around.

“Our family has been coming to Cape Cod for over 100 years through many generations of sailing, crabbing, golfing, long walks on the beach and good family fun,” says Christina O’Donnell, who owns the property with her husband, Tad. We hope it is a tradition that will continue for a long time.”


25 Oyster Way
Type: Waterfront
Bedrooms: 5
Baths: 4 full, 1 half
Price: $15,000 per week



The Mellon Estate, which is also on Oyster Harbors, is a 26-acre oasis. The estate was owned by the late Paul and Rachel “Bunny” Mellon. The home itself was built in 1954. Paul Mellon, a philanthropist and art collector, succeeded in preserving much of Oyster Harbors, ensuring that the island’s natural beauty remained intact and that it would not be developed for commercial or industrial purposes.

The Koch family purchased Mellon_005-2806696the estate in 2012 for $19.5 million and have preserved much of it, including a nine-bedroom, 7,000-square-foot home where the Mellons lived and that now serves as a summer rental. There is a simple elegance to the home. Much of its old Cape Cod charm has been retained, with original windows and doors and beautiful wide-plank wood floors. The lovely bedrooms have all been redecorated. It is a sprawling residence that wraps around the grounds and allows for an ocean view from nearly every room in the house. The lush grounds are well manicured.



The large, central sitting room is a perfect place for family and friends to gather, while the dining room, featuring floor-to-ceiling windows, has one of the best views in the house. Step outside for a panoramic view of Seapuit River, Sampsons Island and Nantucket Sound. There is plenty of comfortable seating for everyone to enjoy a cocktail and appetizers. A path down to the water leads to a beach house with tables and chairs, a small kitchen and a dock.

The Mellon Estate is the perfect summer retreat; a place of quiet luxury.


Mellon Estate, Oyster Harbors
Type: Waterfront
Bedrooms: 9
Baths: 9 full, 0 half
Price $25,000 per week


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