Capeside
Timeless Cape Cod character meets sophisticated modern comfort in this beautifully renovated three-bedroom, four-and-a-half-bathroom antique home in Orleans. Thoughtfully curated furnishings complement original architectural details, while a stunning chef’s kitchen and spacious living areas create an elegant setting for gathering. A converted gallery adds distinctive charm with vaulted ceilings, original beams, a wet bar, and loft, while an additional media space provides even more room to relax and unwind. Outside, a welcoming patio overlooks manicured grounds and a spacious lawn ideal for dining, games, and leisurely afternoons in the coastal air. Ideally positioned between Orleans and Chatham, the home offers convenient access to both downtown areas, celebrated beaches, golf, dining, and boutique shopping. Pleasant Bay is also nearby for kayaking and paddleboarding, making this refined retreat an exceptional setting for experiencing the best of Cape Cod.
Our promise
We've reviewed thousands of homes and approve only the best. Each one is professionally managed and vetted for comfort and style, raising the bar for every stay.
KEY Curation Notes
Amenities
Elevate your stay with add-on services
Book a home, then customize your experience. From beach gear delivery to pre-arrival groceries and private chefs, we coordinate everything you need so you can make memories in the waves and stories at sunset.
-500x500.jpg)
Bedroom details
Location
Inside the destination
Neighborhood: South Orleans - 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.
Parking information
During peak hours at town beaches, parking stickers are required. Of course, most of our properties are directly on or within easy walking distance of private, neighborhood association beaches, so no pass is required. For those properties that aren’t right on or within walking distance a pass is necessary. You can stop by the town offices to pick up a weekly pass or pay per visit. Beach passes are issued by vehicle so are not transferable.
We're here to help
Whether you have questions on this home or want us to source other options, we're a message away!
Reviews
Jen
This is a beautiful property in a great location. The house was spacious and so beautifully designed.
Policies
Cancellation policy
Plans change, we get it.
Enjoy peace of mind when booking with KEY.co.
Partial Refund: Receive a 75% refund when you cancel your reservation at least 120 days before check-in.
No Refund: Reservations canceled 119 days or less before check-in are not eligible for a refund.
Refunds subject to a 5% processing fee of the total.
Things you need to know
Self Check-In / Check-Out
This property has a seven-night minimum during the peak season and rents Friday to Friday during peak weeks or Summer.
Fresh sheets and bath towel sets for each guest are provided. A bath towel set includes a bath towel, hand towel and face cloth. Bed linens at the premises are provided – no need to pack them and bring them with you!
A “starter set” of cleaning/paper products is also provided. There will be paper towels and bath tissue to start off your week. Similarly, you will be provided with cleaning products like dish soap, laundry detergent, all-purpose cleaners, etc. We ask that you replace what you use so the guests coming in after you can enjoy the same convenience. Some kitchen trash bags will also be provided.
Restrictions
Guests & Occupancy
- No more than the number of guests listed on the lease may occupy the property at any time, including infants, children, and overnight visitors.
- Guests are responsible for all damage, loss, or added expenses incurred during the stay (including pay-per-view charges). All known damage or loss must be reported before departure to remain eligible for accidental damage coverage.
Events & Noise
- Weddings, receptions, reunions, or any gathering exceeding the approved occupancy are prohibited without prior written approval. Failure to obtain approval will result in a penalty equal to an additional full weekly rental rate.
Prohibited Activities
- Pets: No animals, birds, or pets of any kind unless explicitly approved in the lease. Violation fee: $5,000.
- Smoking/Vaping: Smoking or vaping is prohibited anywhere on the premises. Violation fee: $5,000.
- Illegal Substances & Fireworks: Illegal activities and fireworks are strictly prohibited.
- Security Cameras: Tampering with, disabling, redirecting, or obscuring exterior security cameras (e.g., Ring doorbell) is prohibited and may result in lease cancellation. No interior cameras are used.
Equipment & Amenities
- Utilities are provided (electricity, water, gas if applicable, heat, trash). Guests must use utilities responsibly and avoid waste.
- Appliances & Equipment _(if equipped)_: Appliances and equipment (HVAC, internet, cable TV, dishwasher, washer/dryer, gas grill) are maintained but not guaranteed. No refunds will be issued for outages or malfunctions.
- Parking: The number of vehicles parked at the property may not exceed the number listed on the lease and must be parked only in assigned spaces. Camper vehicles or vehicles providing sleeping accommodations are not permitted without prior written approval.
Checkout & Care
- Check-in: 4:00–6:00 PM (early arrival only if confirmed). Check-out: 10:00 AM. Guests must text upon departure to notify housekeeping. Late Checkout Fees: $500 per hour (or portion thereof) for up to two hours past checkout. After two hours, additional lease penalties apply. The property must be left clean and in good, habitable condition per the checkout checklist. Lost key fee: $25 per key.
Liability & Disclaimers
- Not responsible for lost or stolen items. Guests must pay shipping and handling for any items requested to be returned after departure.
- Guests assume all risk for injury, loss, or damage resulting from use or misuse of the property or its fixtures and agree to indemnify the landlord and agent.
- May enter the property with reasonable notice to inspect, make repairs, or protect the premises.
- Minor or non-material changes to furnishings, fixtures, equipment, or property details do not constitute liability.
- Failure to comply with lease terms may result in eviction with as little as two hours’ notice and additional charges equal to a full weekly rental rate, plus legal fees if enforcement is required.
- If the property becomes unavailable or uninhabitable due to fire, casualty, or legal violation, rent will be prorated or refunded accordingly. The landlord is not liable for additional losses.
