House in Osterville, MA
20 guests · 8 bedrooms · 7 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
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.
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.
Amenities
Non-smoking
Pets allowed
Map of Osterville, MA
Ratings and reviews
10 / 10Outstanding·Jul 2026
Exceptional beach retreat in Osterville walking distance to town. Perfect for our family reunion with a large kitchen, plenty of places to gather and eat from formal to informal to outside on the patio with a view of the sunset. Access to the water meant no need to go to the town beach (though we did). Very charming family home with lots of character and plenty of places to both gather and play cards or retreat to read a book.
10 / 10Outstanding·Jun 2026
Exceeded expectations. The pictures do not do this place justice....the property, the landscaping, the location, the house....really everything was exceptional. This does not feel like a sterile vacation rental, but rather a cherished family home. The well organized kitchen was stocked with everything you could imagine, the bedding was lovely, the beds comfortable, the host responsive & the patio table with seating for 10 overlooking the water couldn't have been a more lovely place to have dinner. This was the perfect place for our large family to gather. There was a snafu with the wifi that the host helped to resolve in a timely manner. We would love to come again!
10 / 10Outstanding·Nov 2021
Great
10 / 10Outstanding·Oct 2016
Our party consisted of 6 couples in town for a wedding at a nearby club. The property exceeded our expectations with plenty of room, activities and character. This property is in a perfect and private setting with beautiful sunsets and plenty of space to spend outdoors. Our group gravitated to the main house for meals and wandered down to the boat house for a cocktail for the evenings. The guests stayed busy by playing tennis, beach volleyball, billiards, using the hot tub and of course going down the slide! This is a precious home that has been well cared for and is a classic cape experience.
$$$$
Top rated by guests
10Outstanding
(11 Ratings)
"Exceptional beach retreat in Osterville walking distance to town. Perfect for our family reunion with a large kitchen, plenty of places to gather and eat from formal to informal to outside on the pat..."
Brian T.Don't miss out! Price and availability may change
