Osterville, MA Villa Rentals

Osterville Villa

Private Nantucket style home with heated pool and beach pass

Price Dropped

House

Private Nantucket style home with heated pool and beach pass

10.0

Exceptional

(11 Reviews)

4 Bedrooms 3 Baths 10 Guests

US $1,345/Night 7 Nights - US $9,418

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Osterville Gem Steps to Main St! Relax fireside

House

Osterville Gem Steps to Main St! Relax fireside

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 4 Guests 505.9 ft²

US $390/Night 7 Nights - US $2,730

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Highly Rated

Cottage

Charming Cottage Getaway

10.0

Exceptional

(61 Reviews)

2 Bedrooms 1 Bath 3 Guests 500 ft²

US $411/Night 7 Nights - US $2,876

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House

Osterville Odyssey

9.0

Exceptional

(1 Review)

3 Bedrooms 3 Baths 6 Guests 1517.71 ft²

US $876/Night 7 Nights - US $6,129

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Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants

Price Dropped

House

Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants

10.0

Exceptional

(5 Reviews)

2 Bedrooms 1 Bath 6 Guests

US $406/Night 7 Nights - US $2,840

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House

Shake on the Cape

9.0

Exceptional

(1 Review)

4 Bedrooms 2 Baths 10 Guests 1926.74 ft²

US $824/Night 7 Nights - US $5,768

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Cottage

Charming cottage near Osterville Village and Dowses beach RPMS094

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 3 Guests

US $539/Night 7 Nights - US $3,771

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Swing Set Plunge pool and large yard await

House

Swing Set Plunge pool and large yard await

8.0

Excellent

(1 Review)

3 Bedrooms 3 Baths 8 Guests 1345.49 ft²

US $420/Night 7 Nights - US $2,940

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House

Osterville Gem Steps to Main St! Relax fireside

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 4 Guests 500 ft²

US $380/Night 7 Nights - US $2,663

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Walk to Shops & Dining: Cozy Osterville Cottage

House

Walk to Shops & Dining: Cozy Osterville Cottage

8.0

Excellent

(1 Review)

2 Bedrooms 1 Bath 5 Guests 904.17 ft²

US $271/Night 7 Nights - US $1,897

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House

Charming Ranch on the Cape

9.4

Exceptional

(3 Reviews)

2 Bedrooms 1 Bath 5 Guests

US $472/Night 7 Nights - US $3,301

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Elegant Family Osterville Retreat Near Dowses Beach

House

Elegant Family Osterville Retreat Near Dowses Beach

1 Bedroom 1 Bath 10 Guests 2454.17 ft²

US $1,112/Night 7 Nights - US $7,785

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More Top-Rated Villa in Osterville Area

Why Choose Rent By Owner for your Osterville Villa?

What makes our Villa special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Osterville

When should you plan your Villa stay?

Choosing the optimal time to visit here can enhance your experience, as the region offers different attractions and ambience throughout the year, making it essential to plan your trip according to seasonal weather patterns and local events for a memorable vacation in Osterville, Massachusetts.

Peak Season Highlights

Summer (June to August)

This is the most popular time to visit, as you can enjoy warm weather and long daylight hours on the coast.

Average Temperature Daytime: 75-85°F - Nighttime: 60-65°F

Fall (September to October)

During these months, the area is known for its vibrant foliage and mild temperatures, making it ideal for outdoor activities and scenic drives.

Average Temperature Daytime: 65-75°F - Nighttime: 50-55°F

Off-Season Highlights

Spring (April to May)

In spring, the region begins to blossom with fewer visitors, providing a peaceful setting to explore local scenery and enjoy pleasant weather.

Average Temperature Daytime: 55-65°F - Nighttime: 45-50°F

Winter (November to March)

The quieter winter months offer a cozy atmosphere with cooler temperatures, perfect for those seeking tranquility away from peak crowds.

Average Temperature Daytime: 40-50°F - Nighttime: 30-35°F

Weekly Weather Forecast for Osterville

How to Book Your Osterville Villa

What's our booking process?

Our platform allows you to browse a curated selection of villa. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Osterville

More Top-Rated Villa in Osterville Area

Common Villa Amenities

What amenities can you expect?

Our Villa are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy access to a spacious outdoor patio or deck perfect for relaxing evenings and al fresco dining.
Take advantage of private gardens or landscaped yards that enhance your outdoor experience.
Make use of convenient outdoor parking spaces available on the property.
Experience the comfort of furnished terraces offering beautiful views of the surrounding area.
Relax by the outdoor swimming pool, a popular feature in many properties here during warm seasons.
Utilize well-maintained outdoor grills or barbecue areas for cookouts with family and friends.
Benefit from proximity to beaches or waterfront access, ideal for enjoying the region’s coastal charm.

Top Attractions Around Osterville

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities, explore scenic beaches, and indulge in local dining experiences, all within easy reach of your ideal Osterville, Massachusetts accommodation, making it the perfect destination for a relaxing getaway.

Family Activities

Cadillac Mountain Trail: Embark on a family-friendly hike offering scenic views, perfect for experiencing the natural beauty of this region.
Marina Activities: Enjoy a day of boating, kayaking, or paddleboarding at the marina, providing fun water-based adventures for all ages.
Local Beaches: Spend relaxing afternoons on the pristine beaches, ideal for swimming, building sandcastles, or picnicking with your loved ones.
Children’s Nature Programs: Participate in educational programs and outdoor activities designed to engage children with the area's rich natural environment.

Adult Activities

Bird Watching and Nature Walks: Discover the diverse local wildlife and scenic landscapes with leisurely walks through protected natural areas nearby.
Fishing Excursions: Enjoy a relaxing day casting lines at popular fishing spots that promise a tranquil escape along the coastlines of this charming region.
Historic Tours and Museums: Explore the area's rich maritime history and heritage through guided tours and engaging museum exhibits.
Golfing Experiences: Play a round on well-maintained golf courses that offer beautiful views and challenging holes, perfect for your leisure time.

Other Places to Stay in Osterville, MA

Osterville Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Visit During Off-Peak Seasons: Visiting during the quieter months allows you to enjoy the area’s natural beauty and tranquility at a more relaxed pace, making your stay in this destination truly memorable.
Explore Local Dining Options: Indulge in the region’s fresh seafood and charming eateries to experience authentic flavors that complement your villa retreat.
Take Advantage of Water Activities: The area’s proximity to water offers opportunities for kayaking, boating, or fishing, enhancing your experience here with outdoor adventures.
Discover Hidden Gems and Scenic Spots: Wander off the beaten path to uncover scenic viewpoints and peaceful beaches that showcase the natural beauty of this destination.

Transportation Options

Car Rentals: You can easily rent a car here to explore Osterville and the surrounding region at your own pace.
Public Transit: The area is served by local bus services that provide convenient transportation options for visitors staying in nearby villas.
Taxis and Rideshare Services: Taxis and rideshare companies like Uber and Lyft offer flexible and accessible transportation throughout this destination.
Biking and Walking: The scenic pathways and sidewalks make biking or walking an enjoyable way to experience the region’s charming surroundings.

Local Customs Options

Seafood Etiquette: Locals here take pride in their fresh seafood, and you’ll find that sharing in a communal clamming or fishing experience is a cherished tradition.
Respect for Nature: It’s customary to leave natural sites undisturbed, reflecting the area's commitment to preserving its scenic beauty and coastal environment.
Historical Reverence: Visitors often observe a respectful attitude towards local history, especially when exploring landmarks and participating in community events.
Festive Celebrations: During seasonal festivals, engaging actively and with consideration for local customs enhances your experience of this inviting destination.

Osterville Villa Frequently Asked Questions

1. What are the top Villas in Osterville?

There are a lot of options in Osterville. If you plan on staying in the Osterville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Villas in Osterville:

2. How many Villas are available in Osterville?

Currently, the total number of properties listed by RBO in 2026 is over 164 in the Osterville area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Osterville. 

3. What is the cancellation policy for villas in Osterville, Massachusetts?

The cancellation policy varies depending on the specific villa listing. It’s important to review the terms outlined on the property page or contact the owner directly for detailed information.

4. Are there any additional fees associated with booking a villa in this destination?

Additional fees such as cleaning, service charges, or security deposits may apply. These details are specified in each listing, so be sure to read the full description or reach out to the host for clarification.

5. How do I know if a villa in the region is available for my travel dates?

Availability status is shown on each listing. If your dates are not available, consider contacting the owner for possible adjustments or explore alternative options within the area.

6. What amenities can I expect when staying at a villa in this area?

Amenities vary by property but often include essentials like Wi-Fi, parking, and fully equipped kitchens. Specific amenities are listed on each property page, allowing you to choose accommodations that suit your needs.

7. Who should I contact if I encounter issues during my stay at a villa in Osterville?

You should reach out to the property owner or host directly. Contact details are typically provided in your reservation confirmation to ensure prompt assistance during your visit.