Windward Retreat
Overlooking the tranquil waters of Kelly’s Pond, this exceptional waterfront retreat combines sophisticated design with the relaxed charm of Cape Cod living. The open-concept main level is thoughtfully designed for gathering and entertaining, featuring an expansive chef’s kitchen with an oversized island that flows seamlessly into inviting living and dining spaces. A private study offers additional flexibility, while custom details and stylish finishes throughout create a warm and welcoming atmosphere. Upstairs, beautifully appointed bedrooms provide peaceful accommodations, including a stunning primary suite with a spa-inspired bath designed to showcase picturesque pond views. Outdoor living takes center stage with expansive decks offering the perfect setting to enjoy summer days and coastal breezes. Relax in the outdoor shower, gather for meals in the outdoor dining areas, or launch a kayak from the private dock for a day on the water. The home also features a spacious lower-level recreation area, a half basketball court that can be converted for pickleball, and easy access to nearby beaches, including West Dennis Beach less than a mile away. Blending waterfront serenity with outstanding amenities, this remarkable home offers an unforgettable Cape Cod escape.
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: West Dennis - Situated on Kelly's Pond. If you want to spend the day at an ocean beach, West Dennis Beach is less than one mile away.
Parking information
A larger, circular driveway provides plenty of parking.
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Reviews
We thoroughly enjoyed our weeklong stay with our family. We spent our days swimming in the pond, rinsing off in the outdoor shower and taking walks to the sound. We like to cook and found the kitchen to be very well stocked. The views from the home (especially from the kitchen and upstairs in the master bathroom) are so calming. We also enjoyed playing games at the built-in table in the family room. We hope to be back soon!
Policies
Things you need to know
A half basketball court will provide endless opportunities for rousing games (and can be turned into a pickleball court with the supplied net).
Guests provide their own linens and towels.
Sat. to Sat., 7-night minimum during the peak season. 4-night minimum during the shoulder seasons at a reduced rate.
A full suite above the garage that features a private entrance, 1 bedroom w/ king bed and 1 full bathroom w/ shower is available to add onto your rental with an additional charge in rent. Please inquire for details. Photos at the end of the listing show the suite.
Restrictions
Guests & Occupancy
- Primary Guest must be 25+ and present for the entire stay; violations may result in cancellation or eviction without refund
- Limited to stated sleeping capacity; over-occupancy may result in eviction without refund
- Primary Guest is responsible for all damages, charges, and rule compliance; credit card on file may be charged
- Use is limited to vacation/recreational purposes only
- Motor homes, campers, and tents are not permitted (violation may result in termination without refund)
Events & Noise
- Events: Weddings, parties, reunions, or large gatherings are not permitted
- Noise compliance: Must follow all local noise and occupancy ordinances
Prohibited Activities
- Pets: Not allowed unless pre-approved with signed addendum; non-refundable fees apply; violations may result in eviction, loss of deposit, and additional charges
- Smoking: Strictly prohibited; Guest responsible for any odor or damage-related charges
- Fire hazards: No campfires, fireworks, or open flames unless explicitly allowed
- Illegal/unauthorized use: Subletting and unapproved use are prohibited
- Unapproved modifications: Installing equipment (e.g., window A/C) or altering the space is not allowed; damage/repair costs apply
Equipment & Amenities
- HVAC & utilities: Doors/windows must remain closed when A/C is in use to prevent damage; misuse may result in repair charges
- Appliances & systems: Operation is not guaranteed; no refunds for malfunctions (includes A/C, internet, appliances, power outages, etc.)
- Internet/phone/TV _(if equipped)_: Long-distance calls and paid media are charged to Guest
- Provided items: Guests may need to bring linens, towels, and supplies unless otherwise stated; rentals may be available for a fee
- Equipment reporting: Damage must be reported within 24 hours; unreported or excess damage beyond coverage (up to $1,000 or $300 for shorter stays) is chargeable
- Locked areas: Restricted areas are off-limits; unauthorized access may result in charges
- Maintenance access: Authorized personnel may enter for inspection, repairs, or showings with notice where required
Checkout & Care
- Cleaning expectations: Must leave in clean, habitable condition; excess cleaning fees apply
- Damage reporting: Report cleanliness or maintenance issues within 24 hours of check-in
- Furniture & care: Return furniture to original placement; moving damage or misplacement may incur fees
- Trash: Must be properly disposed of per instructions; excess trash removal may incur charges
- Checkout compliance: Late checkout may incur fees up to $100 per 30 minutes
- Keys: Lost keys incur a $60 replacement fee
Liability & Disclaimers
- Not responsible for lost items; return shipping costs apply; unclaimed items may be discarded after 30 days
- Not liable for injury, illness, or damage occurring during the stay
- No refunds for non-essential failures (appliances, utilities, internet, etc.)
- No liability for weather, pests, allergens, or natural conditions
- Natural disasters: If uninhabitable, limited to a pro-rated refund of rent paid only
- No refunds or relocation for nearby construction disturbances
- Rented as-is; no refunds if expectations are not met
- Furnishings and features may change without notice; not guaranteed
- Errors or omissions in descriptions are not guaranteed
- Rates & availability: Subject to change without notice
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