Port Manor
Set on 1.61 beautifully landscaped acres in Chatham, this remarkable estate blends historic New England character with exceptional space for gathering and relaxation. Originally owned by a sea captain more than 220 years ago, the expanded Colonial-style home showcases timeless architectural details, exposed beams, and thoughtfully updated interiors. The main house features a fully renovated kitchen, an impressive dining room, multiple inviting living spaces, and six well-appointed bedrooms, including two primary suites. Bordering the prestigious Eastward Ho! golf course and overlooking the natural beauty of Pleasant Bay, the property offers a peaceful setting just minutes from Jackknife Cove Beach and Strong Island Landing Beach. The outdoor experience is equally unforgettable, with expansive lawns, charming grape arbors, a wishing well, and a large private heated pool complemented by a fully equipped cabana. A spectacular guest house and barn add even more character, highlighted by a soaring great room with dramatic exposed beams, along with its own kitchen, bedrooms, and baths. Modern comforts, including central air or high-efficiency split units, smart TVs, and high-speed Wi-Fi, ensure a seamless stay, while the estate’s unique blend of history, luxury, and privacy creates an extraordinary Cape Cod retreat for families and groups seeking a truly memorable escape.
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KEY Curation Notes
Amenities
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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.
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Bedroom details
Location
Inside the destination
Neighborhood: Eastward Ho / Pleasant Bay Area - Set on 1.61 private acres near Pleasant Bay, the property is just a 2-minute drive to Jackknife Cove Beach and minutes from Strong Island Landing Beach.
Parking information
- Parking space available. - 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 and are not transferable.
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Reviews
Charles
Very nice property with plenty of space for our large group. The kitchen is a little small but that is made up for with a large finished barn and a beautiful pool. The large property is set beside a golf course which adds to the peaceful surroundings.
Policies
Cancellation policy
Plans change, we get it.
Enjoy peace of mind when booking with KEY.co.
75% 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.
The pool is open from Memorial Day through Columbus Day weekend.
Please note that the Guest House (Barn) is fully winterized (closed) from Mid-October through April for off-season stays each year. As a result, the property only has 6 bedrooms and 5.5 bathrooms, sleeping a maximum of 14 guests.
The main part of the barn is not air-conditioned, just the bedrooms and the kitchen/living room area.
This property has a seven-night minimum during the peak season (Rents Friday to Friday).
This property offers a three-night minimum stay during select weeks in May–June and September–November.
Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more, and the cleaning fee is waived.
Each property will have fresh sheets and bath towel sets for each guest. A bath towel set includes a bath towel, a hand towel, and a face cloth. Bed linens at the premises are provided – no need to pack them and bring them with you!
You will be provided with a “starter set” of cleaning/paper products. 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.
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