Sail Loft
Set on a sprawling acre-plus property in the heart of Chatham, this beautifully updated family compound combines classic Cape Cod charm with modern luxury. Featuring a spacious main house and a separate pool house, the property comfortably accommodates up to ten guests while offering plenty of room to gather and unwind. The resort-style outdoor space is centered around a heated in-ground pool and hot tub, complemented by multiple dining and lounge areas, an outdoor shower, fire table, beverage center, and two gas grills. Best of all, Chatham’s charming village shops, restaurants, Oyster Pond Beach, and iconic Lighthouse Beach are all within an easy walk or bike ride. Inside, the main house offers a thoughtfully renovated kitchen with granite countertops and a center island, along with inviting living spaces designed for comfort and connection. The primary suite is conveniently located on the main level, while additional bedrooms upstairs provide flexible accommodations for families and groups. Just steps from the pool, the pool house adds even more space to relax with its rustic lodge-inspired design, vaulted ceilings, full kitchen, family room, ping pong table, and additional sleeping quarters. Modern conveniences, including central air conditioning, high-speed Wi-Fi, SONOS audio, and multiple TVs, ensure every stay is as comfortable as it is memorable, creating the perfect setting for an exceptional Chatham getaway.
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 - Ideally located within walking distance of Chatham Village’s shops, restaurants, and entertainment, with Oyster Pond Beach and Lighthouse Beach both less than a 15-minute walk away.
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.
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.
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.
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 persons listed on the lease (including infants, children, and overnight visitors).
- Only the number of vehicles listed on the lease may park on the property. No camper vehicles with sleeping accommodations without prior written approval.
- Property is for vacation/recreational use only.
- Additional full weekly rental rate penalty if occupancy exceeds lease limits.
- Rents Friday to Friday in Peak Season.
Events & Noise
- Weddings, receptions, reunions, or gatherings exceeding lease occupancy require prior written approval. Violation results in an additional full weekly rental rate penalty.
- No refunds for noise or disturbances, including nearby construction not owned by Landlord.
Prohibited Activities
- No animals, birds, or pets unless specifically authorized in lease. Violation: $5,000 penalty.
- No smoking permitted. Violation: $5,000 penalty.
- Use of illegal materials, including fireworks, is prohibited.
- Exterior security cameras may be in use. Tampering, disabling, or obstructing cameras may result in lease cancellation. No interior cameras.
Equipment & Amenities
- Landlord provides electricity, water, gas (if applicable), heat, and trash removal. Tenant must avoid waste.
- Landlord will make reasonable efforts to repair equipment but does not guarantee against failure (A/C, internet, cable TV, dishwasher, washer/dryer, grill, etc.). No refunds for appliance or system malfunctions.
Checkout & Care
- Tenant must leave property in clean, good, and habitable condition per Checkout Checklist.
- All damage, loss, added expenses, and pay-per-view charges must be reported before departure. Failure to report may void damage protection coverage.
- $500 per hour (or portion thereof) up to 2 hours past checkout. Beyond 2 hours, additional lease penalties apply.
- $25 per lost key.
Liability & Disclaimers
- Trip insurance is strongly recommended.
- Not responsible for lost/stolen items.
- Tenant assumes responsibility for injury, loss, or damage caused by Tenant or guests and agrees to indemnify Landlord/Agent.
- Tenant must vacate upon required notice if in default. Holdover or refusal to vacate results in additional full weekly rental rate plus applicable per diem and attorney fees.
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