Rare Osterville Waterfront Compound - Private Beach, Dock, Hot Tub & Sunset View | House in Barnstable
8 Bedroom House in Wianno, Barnstable
Welcome to Anchor to Windward, a private waterfront retreat in the heart of Osterville. Set on two acres overlooking West Bay, this special property features a private beach, deep-water dock, spectacular west-facing sunsets, and two separate homes with 8 bedrooms and 7.5 bathrooms — offering plenty of space for families and groups of up to 20 to gather, relax, and enjoy Cape Cod.
The property includes a five-bedroom Main House and a separate three-bedroom Boat House directly by the water. The two-house layout is ideal for multigenerational family vacations and larger groups, giving everyone their own space while keeping the entire group together on one private property.
Spend your mornings swimming, kayaking, or paddleboarding from the beach, afternoons relaxing by the water, and evenings gathering for dinner on the waterfront patio before watching the sun set over West Bay. End the night in the seven-person hot tub overlooking the water.
THE PROPERTY
Main House — 5 Bedrooms
The Main House is designed for gathering, with bright, comfortable living spaces and beautiful views of West Bay throughout the home.
The waterfront sunroom is a favorite place to enjoy morning coffee, read a book, or watch the sunset. The fully equipped kitchen offers plenty of space for preparing meals for a group and opens to the family room and billiards area. Multiple indoor and outdoor dining and living spaces make it easy for everyone to spend time together without feeling crowded.
The Main House includes five bedrooms, all with water views, along with beautifully appointed bathrooms, air conditioning, laundry facilities, and an additional refrigerator.
Boat House — 3 Bedrooms
Just steps from the beach, the separate three-bedroom Boat House offers additional privacy and its own living space while keeping guests close to the Main House.
It's an ideal setup for grandparents, another family, older children, or anyone who appreciates having a little extra space during a group vacation. With the water right outside, the Boat House offers the quintessential Cape Cod experience.
WATERFRONT LIVING
The waterfront is what makes Anchor to Windward truly special.
Enjoy your own private beach on West Bay, swim directly from the property, launch a kayak or paddleboard, or spend the afternoon relaxing by the water. A deep-water dock provides direct access to the bay, while the outdoor shower and beach changing areas make coming and going from the water easy.
At the end of the day, gather around the teak outdoor dining table for dinner overlooking the bay, relax in the seven-person hot tub, or simply settle in to watch the sunset — the property's western exposure makes for spectacular evenings over the water.
HIGHLIGHTS
• Private waterfront property on approximately two acres
• Private beach on West Bay
• Deep-water dock
• 8 bedrooms across two separate homes
• 7.5 bathrooms
• Accommodates up to 20 guests
• Water views from many bedrooms and living spaces
• Separate three-bedroom Boat House
• Seven-person waterfront hot tub
• Outdoor dining overlooking West Bay
• Swimming, kayaking and paddleboarding directly from the property
• Outdoor shower and beach changing areas
• Billiards table
• Fully equipped kitchen
• Wet bar, wine refrigerator and ice maker
• Air conditioning
• Laundry facilities and second refrigerator
OSTERVILLE
Despite its peaceful and private setting, Anchor to Windward is just about one mile from the heart of Osterville Village.
Bike, walk, or drive into town for coffee, breakfast, shopping, groceries, and dinner, or spend the day exploring the beaches and villages of Cape Cod. Hyannis and the ferries to Nantucket and Martha's Vineyard are also a short drive away, making day trips easy.
Whether you're planning a multigenerational family vacation, a summer reunion, or simply looking for a beautiful place where everyone can be together, Anchor to Windward offers a rare combination of privacy, space, waterfront access, and proximity to Osterville Village.
Come experience summer on West Bay at Anchor to Windward.
Rare Osterville Waterfront Compound - Private Beach, Dock, Hot Tub & Sunset View is located in Wianno. Rare Osterville Waterfront Compound - Private Beach, Dock, Hot Tub & Sunset View provides accommodation, featuring Balcony/Terrace, Wellness Facilities, Child Friendly, among other amenities. This House features Air Conditioner, Parking and Pet Friendly to make your stay a comfortable one.
Rare Osterville Waterfront Compound - Private Beach, Dock, Hot Tub & Sunset View has 8 Bedrooms , 7 Bathrooms, and max occupancy of 20 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Wianno has interesting places to visit. If you want to learn more about the House in Wianno, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Facility Overview
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Heating
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Air conditioning
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Bathtub or shower
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Soap
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7+ bathrooms
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Jetted bathtub
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Towels provided
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Toilet paper
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Hair dryer
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8 bedrooms
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Bed sheets provided
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Dining table
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Dining room
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Fireplace
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Coffee/tea maker
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Oven
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Stovetop
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Electric kettle
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Paper towels
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Refrigerator
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Dishwasher
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Spices
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Microwave
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Washing machine and dryer
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Laundry facilities
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Beach towels
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Beach sun loungers
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On the beach
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Onsite parking
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1 total (up to 50 lbs per pet)
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Service animals exempt from fees
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Pet friendly
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Welcoming dogs only
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If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
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No elevators
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Smoke-free property
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Upper floors accessible by stairs only
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Marina nearby
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Fishing nearby
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Bicycle on site
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Water sports equipment
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Kayak on site
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Power boating nearby
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Whale watching nearby
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Wildlife and game walks nearby
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Water tubing nearby
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Golfing on site
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Fitness facilities nearby
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Golf nearby
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Birdwatching nearby
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Water skiing nearby
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Books
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Smart TV
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Stereo
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Arcade/game room
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Pool or billiards table
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Games
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Printer
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Desk chair
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Desk
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English
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Recycling
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Near a hospital
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Near outlet shopping
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Next to a golf course
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On the waterfront
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Near the sea
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Near the bay
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Near a health or beauty spa
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Iron/ironing board
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Phone
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Children's games
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Children's dinnerware
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Highchair
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Playground
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Children's toys
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Travel crib
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Children's books
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WiFi available
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Garden
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Balcony
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Outdoor furniture
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Barbecue grill
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Firepit
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Deadbolt lock
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Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
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Smoke detector installed (host has indicated there is a smoke detector on the property)
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Fire extinguisher
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Hot tub
Policies
Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed onsite parties or group events are strictly prohibited host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property safety features at this property include a fire extinguisher and a deadbolt lock this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation property registration number c0154430200
Reviews
FAQ's
Is this property pet-friendly for guests?
Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.
Does the property have a swimming pool?
No, this Wianno house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in property?
Best-rates for the Wianno house starts from $2,348 per night with includes Air Conditioner, Parking, TV, View, Sports/Activities, Hot Tub, Oceanfront, Bedding/Linens, Guest Services, Kitchen, Balcony/Terrace, Wellness Facilities, Child Friendly, Heating, Laundry, Pet Friendly, Ocean View, Security/Safety, Fireplace, Entertainment, Barbecue/Outdoor Cooking, Internet with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is property a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the property wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Wianno house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the property?
Based on the information reported by the owner or manager, the Wianno house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for property?
Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
