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8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay

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Anchor to Windward
Driveway Entrance View
Sunset Views
Private Dock
Patio off Sunroom - Main House

Reviews

10 out of 10
Exceptional

Highlights

  • On the beach
    A rare beachfront property in the area - enjoy direct access to the sand and sea.
8 bedrooms7+ bathroomsSleeps 20

Popular amenities

  • On beach
  • Spa pool on site
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine

Explore the area

View map
Barnstable, MA
  • Place, Stand Up & Paddle Cape Cod
    ‪2 min drive‬
  • Place, Public Beach
    ‪3 min drive‬
  • Place, Dowses Beach
    ‪6 min drive‬
  • Airport, Hyannis, MA (HYA-Barnstable Municipal)
    ‪18 min drive‬

Rooms & beds

8 bedrooms (sleeps 20)

Bedroom 1 - Primary Bedroom - Main House

1 King Bed

Bedroom 2 - Main House

1 Queen Bed

Bedroom 3 - Main House

2 Single Beds

Bedroom 4 - Main House

1 King Bed

Bedroom 5 - Main House

1 Queen Bed

Bedroom 6 - Primary Bedroom - Boat House

1 King Bed

Bedroom 7 - Boat House

1 Queen Bed and 1 Single Bunk Bed

Bedroom 8 - Boat House

1 Queen Bed and 1 Single Bunk Bed

7 bathrooms, 1 half bathroom

Bathroom 1 - Primary Ensuite Bathroom Main House

Soap · Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Hair dryer

Bathroom 2 - Ensuite Bathroom Main House

Soap · Towels provided · Shower only · Hair dryer

Bathroom 3 - Ensuite Bathroom Main House

Soap · Towels provided · Bathtub or shower · Hair dryer

Bathroom 4 - Ensuite Bathroom Main House

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 5 - Ensuite Bathroom Main House

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 6 - Primary Ensuite Bathroom Boat House

Soap · Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Hair dryer

Bathroom 7 - Hall Full Bathroom Boat House

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Hair dryer

Bathroom 8 - Half Bath 1st Floor of Main House

Soap · Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay

Our family home "Anchor to Windward" features 8 bedrooms and 7.5 baths on a 2-acre lot consisting of a main house with 5 bedrooms and 5.5 baths and a boathouse with 3 bedrooms and 2 baths overlooking a private beach on West Bay in Osterville, MA. The majority of bedrooms all have water views! The property features a deep water dock perfect for fishing and an outdoor 7-person seasonally operated hot tub/spa on an elevated deck with sunset views. The boat house has its own kitchen/family room and a garage/room that can be used for small gatherings. There is also an outdoor shower & changing rooms by the beach that guests are welcome to use. The main house features an updated high-end kitchen with wet bar, ice machine and wine cooler, and a full sized billiard table in the family room off the kitchen -- perfect for entertaining and family gatherings. Start your day swimming, paddle boarding, or kayaking in the bay and finish it off with a cocktail in the sunroom with wall-to-wall windows overlooking spectacular sunset views. Our home has A/C throughout and is located a short bike ride (1 mile) into Osterville for boutique shopping, groceries, and local coffee shops. Catching the island ferry for a day trip to Nantucket or Martha's Vineyard is just a quick 15 minute drive to Hyannis. Nothing is missing from this gorgeous and perfectly located summer home!

Note: During winter rental months, the boathouse is closed for the season.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Property owner has right to raise damage deposit
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit one pet total)
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number C0154430200
Property # 4891132vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Osterville

Located in Osterville, this holiday home is next to a golf course and on the beach. Hyannis Harbor is a notable landmark, and the area's natural beauty can be seen at Cape Cod Beaches and Mayflower Beach. Travelling with kids? Consider Stand Up & Paddle Cape Cod and Cotuit Center for the Arts. Looking to get your feet wet? Kayaking, waterskiing and water tubing adventures can be found near the property.
View more Holiday homes in OstervilleOpens in a new window
Map
Barnstable, MA

What's nearby

  • Stand Up & Paddle Cape Cod - 2 min drive - 1.5 km
  • Public Beach - 3 min drive - 2.5 km
  • Dowses Beach - 6 min drive - 3.9 km
  • Centerville Historical Museum - 8 min drive - 6.4 km
  • Craigville Beach - 10 min drive - 7.8 km

Getting around

  • Hyannis Transportation Center - 23 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 25 min drive

Restaurants

  • ‪Honey Dew Donuts - ‬11 min drive
  • ‪Dunkin' - ‬8 min drive
  • ‪Osterville Fish Market - ‬6 min drive
  • ‪Dunkin' - ‬3 min drive
  • ‪Dunkin' - ‬9 min drive

Frequently asked questions

Is 8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much does it cost to stay at 8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay?

As of 20 June 2026, prices found for a 1-night stay for 2 adults at 8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay on 20 October 2026 start from NZ$4,205, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at 8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay?

On-site parking is available at the property.

What time is check-in at 8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay?

Check-in begins at 4:00 PM.

What time is check-out at 8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay?

Checkout is at 10:00 AM.

Where is 8 Bedroom Home on Private Beach with Sunset Views Overlooking West Bay located?

Located in Osterville, this beachfront holiday home is next to a golf course and within 1 mi (2 km) of Stand Up & Paddle Cape Cod and Cape Cod Beaches. Public Beach and Dowses Beach are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Conor L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great experience

Great
Stayed 3 nights in Nov 2021
Archival

10/10 Excellent

Mike M.

Classic Cape Compound

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.
Archival

10/10 Excellent

John C.

Beautiful Home, Beautiful Setting

This house is huge and beautiful. We arrived with 16 members over three generations of our family. The house and property were immaculate. The 16 of us were accommodated comfortably between the house and boathouse. The house is beautifully furnished. There are 2 large eating areas, the formal dining room, and a nice sized breakfast room off a large modern, fully equipped kitchen. A large laundry room also houses an extra refrigerator. Off the comfortable living room is a less formal sunroom, ideal for morning coffee and evening cocktails, overlooking the outdoor terrace and the sailboats in the bay. The whole house is suffused with light and the gentle breeze off the water giving the place a cool comfort on the warmest of days. Upstairs, all bedrooms look out on the water. A casual and inviting boathouse is perfect for sunset cocktails while the kids play on the dock and beach. And most memorable are those sunsets over the bay.
Verified

10/10 Excellent

Julia K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

This home was magical . Couldn’t have asked for or wanted more.

Stayed 6 nights in Jun 2025

About the host

Hosted by Long Ellis

Host profile image

What makes this property unique

Anchor to Windward has been in our family for over 50 years. We would love to share our special place with you. Come see what makes this home so unforgettable.

Languages:

English
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