This property is professionally managed by Pretty Picky Properties

Vintage Luxury in Orleans

NEW Listing in 2026!

Sleeps up to 10
3 Bedrooms, 4.5 Baths
Linens Included, Beds Made
Rents Friday to Friday in Peak Summer

Tucked away in the heart of Orleans, “Capeside” is a renovated antique home blending timeless Cape Cod charm with elevated, modern luxury—creating a retreat that feels both refined and effortlessly welcoming.

Inside, the home has been thoughtfully reimagined with all-new furnishings, expertly curated to complement its original character. The stunning chef's kitchen anchors the main level, offering a beautiful and functional space for gathering, cooking, and entertaining. Just beyond, the primary living area invites relaxation with a spacious sectional—perfect for unwinding after a day at the beach.

A truly unique highlight is the converted gallery-turned-family room, where vaulted ceilings, original beams, and a wet bar create an airy, sophisticated space ideal for entertaining or quiet evenings in. A loft above adds an extra touch of charm and flexibility.

The home features three beautifully appointed bedrooms. The first-floor suite offers convenience and comfort with a queen bed with private ensuite, while upstairs you'll find a serene primay king suite along with an additional guest bedroom with queen bed -- each designed as a private retreat.

An additional interior space provides exceptional flexibility, featuring daybeds with trundles and a large TV, along with a full bath—perfect for extra guests, kids, or a relaxed media room setup.

Step outside to enjoy the home's inviting exterior living areas, where a patio overlooks manicured grounds and a spacious lawn—ideal for outdoor dining, games, or simply soaking in the Cape Cod air.

Perfectly situated on the border of Orleans and Chatham, this home offers the ultimate Cape Cod lifestyle. Enjoy the rare convenience of being equidistant to the boutiques and dining of both downtown areas, while remaining just a short drive from the region's most iconic beaches. For water enthusiasts, you are only a half-mile from the Pleasant Bay town landing—perfect for launching kayaks and paddleboards. Whether you are looking to spend the day on an award-winning golf course or seeking a private, stylish retreat, this location provides an exceptional setting for your next escape.

Please enter your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all rental terms less than 31 days that total 14.45%.

Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod.

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