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Whispering Pinescape

4 bedrooms·4.5 bathrooms·8 guests·3,587 sq/ft
Beach access
Pool

Located on one of Osterville’s most sought-after streets, this elegant Cape Cod retreat offers luxury, privacy, and exceptional outdoor living just moments from the beaches of Nantucket Sound. The spacious open-concept layout is designed for effortless gathering, featuring a beautifully appointed kitchen, dining area with direct access to the backyard, inviting sitting spaces, and a comfortable living room perfect for relaxing after a day by the water. A heated pool, expansive private yard, fire pit, and outdoor shower create a resort-like setting ideal for enjoying warm summer days and peaceful evenings under the stars. Thoughtfully designed across multiple levels, the home offers comfortable accommodations and flexible living spaces perfect for families and groups. The finished lower level adds additional lounge space and entertainment options, while amenities such as a ping pong table, beach chairs, beach towels, gas grill, and beach pass enhance the effortless coastal lifestyle. Just minutes from Osterville Village’s charming shops and dining, this sophisticated getaway captures the very best of Cape Cod living.

Our promise

Satisfaction Guarantee

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

A beach pass provides direct access to Nantucket Sound beaches, a short drive from the house. Beach towels, chairs, and toys are supplied, simplifying pool and beach days.
The heated pool and fire pit anchor a spacious private yard. An outdoor kitchen with a gas grill is ready for entertaining and alfresco dining.
The primary suite sits on the first floor with an en-suite bathroom, walk-in closet, and direct yard access. A second primary suite upstairs provides flexibility for larger groups or families preferring separate spaces.
The gourmet kitchen is fully equipped for self-catering, with all linens and a starter supply of essentials included. A washer and dryer are on-site for extended stays.
The heated pool and fire pit are centerpieces of the outdoor space. Confirm availability of the advertised hot tub directly with the property before booking, as it is currently offline.

Amenities

Indoor
TV
Air conditioning
Dryer
Internet
Washer
Outdoor
Garden/Backyard
Outdoor grill
Pool
Heated pool
Outdoor dining
Misc
WiFi
Beach pass
Beach chairs
Beach towels
Cooler

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.

Private chef

Private chef

In-home massage

In-home massage

Beach rentals

Beach rentals

Pre-arrival groceries

Pre-arrival groceries

Alcohol delivery

Alcohol delivery

Private driver

Private driver

Bedroom details

Bedroom 1 - First Level: King
Bedroom 2 - Upper Level: Queen
Bedroom 3 - Upper Level: Queen + Double
Bedroom 4 - Lower Level: Two Twins

Location

Inside the destination

Neighborhood: Wianno - Close to the beaches of Nantucket Sound, nearby is the Village of Osterville with shops and dining.

Parking information

Parking is available.

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

Karen S.

We had an fabulous time in Osterville at this gorgeous vacation rental! The home and the location were unbeatable!

Policies

Check-in: 4:00 PM
Check-out: 10:00 AM
Renter's age: 25+ years old
No smoking allowed
No events allowed
Pets allowed by request

Things you need to know

Hot tub not functional.

All linens and towels are included; a starter supply of items for the stay.

Restrictions

Guests & Occupancy

  • The primary renter must be 25+ and remain at the property throughout the stay; violations may result in cancellation or eviction without refund.
  • Overnight occupancy cannot exceed the stated sleeping capacity; violations may result in eviction without refund.
  • The primary renter is responsible for all occupants' compliance with rental terms.
  • The property is for vacation or recreational use only.

Events & Noise

  • Weddings, family reunions, large social functions, gatherings, and events are prohibited; violations may result in termination without refund.
  • All applicable local noise and occupancy ordinances must be followed.

Prohibited Activities

  • Pets: Prohibited unless the property is pet-friendly or prior approval is granted with a signed Pet Addendum. Non-refundable deposits may apply; unauthorized pets may result in additional charges, loss of deposit, or eviction without refund. _(If permitted)_ Pets must be crated when left alone, and waste must be removed.
  • Smoking: Prohibited unless otherwise stated; indoor smoking may result in cleaning, ionization, and damage charges.
  • Fires & Fireworks: Campfires, fireworks, and other fires are prohibited unless approved; wood-burning fireplaces are not permitted.
  • Motor Homes, Campers & Tents: Prohibited on the premises; violations may result in termination without refund.
  • Subletting: Prohibited without the property owner's written permission.
  • Unauthorized Equipment & Alterations: Window A/C units, unauthorized equipment, recreational items, and alterations causing damage or costs are prohibited.

Equipment & Amenities

  • HVAC & Utilities _(if equipped)_: Turn off lights, A/C, heat, TVs, and faucets when not in use; keep doors, windows, and skylights closed while A/C operates. Misuse-related damage may be charged.
  • Telephone & Entertainment (i_f equipped)__:_ Local calls are free; long-distance calls must use a personal payment method. Movie rentals, unauthorized long-distance calls, and other incidental charges are the renter's responsibility.
  • Linens & Towels: Must be supplied by the renter unless otherwise stated; linen packages/rentals may be available for a fee.
  • Equipment, Appliances & Plumbing: Operation of equipment and appliances is not guaranteed; report malfunctions, plumbing, or septic issues promptly. Use only septic-safe products.
  • Maintenance Access: Authorized personnel and licensed vendors may enter as necessary for repairs, care, or maintenance.
  • Locked Areas: Private storage areas are off-limits; unauthorized access or damage may result in charges.
  • Outdoor Furniture _(if equipped)__:_ Secure outdoor furniture and close umbrellas during forecasted weather; related storm damage may not be covered by damage protection.
  • Malfunctions: No refunds for non-essential equipment or amenity failures, including appliances, internet, cable, A/C, doors, or windows.

Checkout & Care

  • Property Inspection & Reporting: Inspect the property at check-in and report any issues; problems encountered during the stay should be reported within 24 hours.
  • Cleaning expectations: Wipe surfaces, wash and return kitchenware, empty the dishwasher, refrigerator, washer, and dryer, sweep or vacuum excess debris when applicable, and leave outdoor areas and grills clean _(if equipped)_. Excessive cleaning may incur charges.
  • Furniture & care: Return moved furniture to its original location; repositioning charges may apply.
  • Trash: Bag, secure, and dispose of trash as instructed; additional pickup or excessive removal fees may apply.
  • Checkout compliance: Follow the access times stated in the rental agreement; unauthorized early access or late departure may incur charges of up to $100 per half hour.
  • Keys: Return keys as instructed; lost keys incur a $60 service charge.
  • Departure Procedures: Return linens as instructed, lock doors and windows, and leave A/C at the arrival setting _(if equipped)_.

Liability & Disclaimers

  • Not responsible for lost, stolen, or forgotten items; return costs apply, and unclaimed items may be discarded or donated after 30 days.
  • Not liable for injury, sickness, loss, or property damage occurring during or after the stay.
  • No refunds or allergen-free guarantee for typical climate conditions, excess moisture, allergens, insects, pests, or related reactions.
  • Temporary power outages are non-refundable. If a natural disaster, act of God, or documented outage renders the property uninhabitable as determined by applicable law or local officials, affected rent may be prorated, excluding applicable commission and not exceeding rent paid.
  • No refunds or relocation for nearby construction or remodeling.
  • Property is rented as-is, subject to applicable habitability standards; unmet personal expectations do not qualify for refunds.
  • Property information is intended to be accurate but is not guaranteed; errors, omissions, or changes to furnishings and equipment may occur.