Sail Loft
Spanning more than an acre in charming Chatham, this beautifully updated family compound combines classic Cape Cod character with resort-inspired amenities and space for up to ten travelers. Two separate residences provide plenty of room to gather or unwind, with renovated kitchens, inviting living areas, central air conditioning, and multiple spaces for dining and entertainment. A covered patio extends the main living space outdoors, while the second residence adds rustic character with vaulted ceilings, exposed beams, a ping pong table, and its own elevated deck overlooking peaceful woodlands. Summer days revolve around the heated in-ground pool, hot tub, and expansive stone patio, complete with abundant lounge seating, outdoor dining, a fire table, grills, beverage center, and outdoor shower. Chatham Village’s restaurants, shops, and entertainment are within walking or biking distance, while Oyster Pond Beach and Lighthouse Beach can each be reached in less than a 15-minute walk. With generous indoor and outdoor spaces in a highly desirable setting, this private retreat offers an exceptional backdrop for memorable Cape Cod escapes.
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.
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Bedroom details
Location
Inside the destination
Neighborhood: Chatham Village - You can walk or bike to the restaurants, shops and entertainment unique to Chatham Village. Or slip into your swimsuit, grab a towel and head to nearby Oyster Pond Beach or famous Lighthouse Beach, your choice. Each less than a 15-minute walk.
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.
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Reviews
Kasumi
We had a wonderful weeklong August family vacation at this property. The check-in process was very smooth and easy with a very nice personal greeting from a property manager, Scott who was ready to answer any questions. The house was ready to welcome us and have fun. The garden was beautiful and lawn was large enough for children and adults to enjoy with multiple activities. The house had plenty of outdoor and indoor games for us to enjoy as well. The pool was very clean and had plenty of seating and umbrellas. The hot tub was a huge hit with the adults and we enjoyed star gazing every night. Communications with the property manager was very easy as they were just a text away and they responded very quickly. It was a vacation we will remember fondly always thanks in huge part to how seamless the stay was. Thank you!
Policies
Cancellation policy
Plans change, we get it.
Enjoy peace of mind when booking with KEY.co.
Full Refund: Receive a full refund (excluding credit card fees) 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 (Rents Friday to Friday).
This property offers a 3-night minimum stay during select weeks in May – June & September – November.
Guests are charged a cleaning fee for all stays less than 7 nights. Stay 7 nights or more, and the cleaning fee is waived.
Pool is open from Memorial Day to Columbus Day weekend.
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. Please 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.
- Not liable for additional losses if the property becomes unavailable or uninhabitable due to fire, casualty, or legal violation; rent will be prorated or refunded accordingly.
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