Vintage Luxury in Orleans
NEW Listing in 2026!
Sleeps up to 10
Linens Included, Beds Made
Rents Friday to Friday in Peak Summer
To view a slide show with captions, click on icon in upper right corner of the photo.
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 bedroom suites, each with a brand-new luxury bathroom. The first-floor suite offers convenience and comfort with a queen bed, while upstairs you’ll find a serene king suite along with an additional guest suite -- 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 $245.00 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 the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.
It’s your vacation. Get Picky!®
Capeside: 540-O
- 3 Beds |
- 4.5 Baths |
- 10 Guests
Description
- Checkin Available
- Checkout Available
- Not Available
- Available
- Checkin Available
- Checkout Available
- Not Available
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Guest Review
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 Baths |
 TVs |
 Comments |
|---|---|---|---|---|
| {[room.name]} |
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Amenities
- Self Check In / Check Out
- All towels and bedding washed in hot water that’s at least 60ºC
- Carbon Monoxide Detector
- Fire Extinguisher
- Smoke Detector
- Air Conditioning (Central)
- Beach Chairs
- Beach Towels
- Blender
- Board Games
- Boogie Boards
- Books
- Classic Cape Décor
- Coffee Maker (Standard)
- Cooking Spices
- Corn Hole Boards
- Covered Porch
- Deck
- Dishwasher
- Fully Equipped Kitchen
- Game Room
- Garage
- Grill (Gas)
- Grocery Provisioning Available
- Hair Dryer
- Ice Maker
- Kayak(s) for guest use
- Kids Toys
- Linens Included (beds made)
- Lobster Pot
- Microwave
- Multiple Ensuite Bedrooms
- Non-Smoking Home
- Not a pet free home
- Outdoor eating area
- Outdoor Fire Pit - Gas
- Outdoor Shower (enclosed)
- Ping Pong Table
- Rents Fri to Fri during peak weeks
- Smart TV/Apple TV
- SONOS System
- Stand Up Paddle Board(s) Provided
- Streaming TV Services Only
- Umbrella For Porch/Deck
- Updated Interior
- Updated Kitchen
- Video Games
- Volleyball/Badminton Net & Gear
- Washer/Dryer
- Wine Refrigerator
- Wireless Internet (WiFi)
- Workspace Available
- NEW Listing for 2026
Vintage Luxury in Orleans
NEW Listing in 2026!
Sleeps up to 10
Linens Included, Beds Made
Rents Friday to Friday in Peak Summer
To view a slide show with captions, click on icon in upper right corner of the photo.
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 bedroom suites, each with a brand-new luxury bathroom. The first-floor suite offers convenience and comfort with a queen bed, while upstairs you’ll find a serene king suite along with an additional guest suite -- 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 $245.00 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 the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.
It’s your vacation. Get Picky!®
- Checkin Available
- Checkout Available
- Not Available
- Available
- Checkin Available
- Checkout Available
- Not Available
{[review.title]}
Guest Review
| Room | Beds | Baths | TVs | Comments |
|---|---|---|---|---|
| {[room.name]} |
{[room.beds_details]}
|
{[room.bathroom_details]}
|
{[room.television_details]}
|
{[room.comments]} |
Secure Booking Experience