Luxury Vacation Rentals in Osterville

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 6 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Osterville

Wander Cape Cod Village

5 bedrooms•5 baths

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Home in Barnstable

5 bedrooms•4.5 baths

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New

Home in Osterville

4 bedrooms•4 baths

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Home in Osterville

7 bedrooms•6.5 baths

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New

Home in Barnstable

5 bedrooms•4 baths

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Home in Barnstable

6 bedrooms•4 baths

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Welcome to Osterville

Find a coastal escape where Cape Cod elegance meets five-star consistency. Our luxury vacation rentals in Osterville pair shingled charm with airy, modern interiors and thoughtful details throughout.

Every Wander home is beautiful and expertly operated, with hotel-grade amenities, ultra fast WiFi, pristine cleaning, and 24/7 concierge. Expect chef-ready kitchens, plush suites, spa-like baths, smart tech, and light-filled living spaces that open to decks and gardens.

Choose from serene retreats near the bays or tucked among pines, each designed for both relaxation and productivity. When you book with Wander, the pictures match the experience and every detail simply works.

Destinations near Osterville

Available soon in Osterville

Home in Barnstable

6 bedrooms•4 baths

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Featured vacation rentals in Osterville

Wander Cape Cod Village

5 bedrooms•5 baths

•

Home in Barnstable

5 bedrooms•4.5 baths

•

New

Home in Osterville

4 bedrooms•4 baths

•

Home in Osterville

7 bedrooms•6.5 baths

•

New

Home in Barnstable

6 bedrooms•4 baths

•

Highlights in Osterville

Experience the quiet coastal elegance of Osterville, featuring pristine beaches, historic charm, and a sophisticated yet laid-back village atmosphere.

Dowses Beach

Osterville Village Shopping District

Osterville Historical Museum

Armstrong-Kelley Park

Crosby Yacht Yard

Sampsons Island Wildlife Sanctuary

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Osterville

Wander Cape Cod Village

5 bedrooms•5 baths

•

Home in Barnstable

5 bedrooms•4.5 baths

•

New

Home in Osterville

4 bedrooms•4 baths

•

Home in Osterville

7 bedrooms•6.5 baths

•

New

Home in Barnstable

5 bedrooms•4 baths

•

Home in Barnstable

6 bedrooms•4 baths

•

View all homes

Most popular amenities for vacation rentals in Osterville

Other popular amenities & vacation types in Osterville

Beachfront vacation rentals in Osterville

Family vacation rentals in Osterville

Large group vacation rentals in Osterville

Discover more of Osterville

Between Nantucket Sound and the calm waters of West Bay and East Bay, Osterville channels the best of the Cape’s coastal character. Dowses Beach offers sweeping sand, salt marsh views, and sunrise walks, while hydrangea-lined lanes and classic shingle architecture set an elegant tone.

Warm tides and gentle breezes define summer days; autumn brings crisp light, quieter shores, and long horizons. From first light over the marsh to golden evenings on the Sound, the village rewards an unrushed pace and an eye for detail.

This effortless coastal rhythm is why Wander’s luxury vacation rentals in Osterville are the perfect choice, whether you travel for work or leisure.

FAQs: Vacation Rentals in Osterville

Why should I book a Wander in Osterville over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Osterville delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Osterville?

Some of our most popular vacation rentals in Osterville include Wander Cape Cod Village, Luxury Oyster Harbors Retreat With World Class Amenities RPAM057, and Heated salt water pool! Luxury home in the village. RPMS099. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Osterville?

Wander offers 6 vacation rentals in Osterville, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Osterville?

You can check-in to Wander vacation rentals in Osterville after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Osterville have WiFi access?

Yes. Every Wander home in Osterville has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.