Discover Your Perfect Osterville Vacation Homes

Osterville Luxury Rentals

See More Osterville Luxury Vacation Rentals
Find More Osterville Villas, Resorts, & Rentals on BedroomVillas

Osterville Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Osterville on PetFriendly.io

Osterville Large Vacation Homes

See More Family Vacation Rentals in Osterville on FVR

Why Choose Rent By Owner for your Osterville Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
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 Vacation Rentals stay?

Choosing the best time to vacation here ensures you experience the area's natural beauty and relaxing atmosphere at its peak, making your stay in Osterville, Massachusetts, truly memorable.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you can enjoy warm weather and longer daylight hours, ideal for relaxing seaside activities in this coastal area.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
autumn
Early Fall (September to October)

The early fall offers pleasant temperatures and fewer crowds, making it a perfect time to explore and unwind in this charming destination.

Average Temperature Daytime: 68°F to 77°F - Nighttime: 50°F to 60°F

Off-Season Highlights

image
Late Fall to Winter (November to February)

During these months, expect cooler weather with fewer visitors, providing a peaceful atmosphere for those seeking solitude and quiet exploration.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
image
Early Spring (March to May)

As the region transitions into spring, the area begins to awaken with mild temperatures, offering a serene setting before the busy summer season begins.

Average Temperature Daytime: 50°F to 65°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Osterville

How to Book Your Osterville Vacation Rental Home

What's our booking process?

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

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

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 Vacation Rentals in Osterville Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 a private outdoor patio or deck for relaxing and dining al fresco amid the scenery.
  • Take advantage of lush, landscaped gardens that enhance your outdoor experience in this coastal region.
  • Make the most of a spacious yard perfect for outdoor games and family gatherings during your stay.
  • Utilize outdoor grilling equipment to savor delicious meals with views of the surrounding area.
  • Explore nearby pathways or trails for walking, jogging, or biking through the scenic landscape.
  • Relax at a private swimming pool or hot tub available at select properties in this seaside destination.
  • Capitalize on waterfront access or proximity for activities like kayaking, paddleboarding, or fishing while here.

Top Attractions Around Osterville

What attractions are nearby?

Within this charming region, you'll find a variety of outdoor activities and scenic spots to explore, offering a perfect blend of relaxation and adventure during your stay.

image
image

Family Activities

  • Dowses Beach: Spend a day at this family-friendly beach, where you can relax on the sandy shores and enjoy safe swimming within calm waters.
  • Wianno Golf Course: Experience a fun round of golf suitable for all ages, set amidst scenic views that capture the region's charming coastal atmosphere.
  • Osterville Historical Museum: Discover local history through engaging exhibits that offer educational fun for children and adults alike in this inviting community setting.
  • Barnstable County Fairgrounds: Attend seasonal fairs, festivals, and outdoor events that bring families together for entertainment and local cultural experiences.
image

Adult Activities

  • Fishing Charters: Enjoy a day on the water with guided fishing trips that allow you to experience the region's rich maritime heritage firsthand.
  • Harbor Cruises: Explore the scenic coastline and learn about local history on a relaxing harbor cruise, perfect for unwinding in this seaside destination.
  • Golfing: Tee off at nearby golf courses offering picturesque views and challenging holes, ideal for adding some leisure to your stay here.
  • Wildlife Watching: Discover diverse bird species and marine life in the area’s protected nature reserves, providing memorable experiences for nature enthusiasts.

Other Places to Stay in Osterville, MA

Dowses Beach
Dowses Beach Vacation Rentals
Stand Up & Paddle Cape Cod
Stand Up & Paddle Cape Cod Vacation Rentals
Public Beach
Public Beach Vacation Rentals
Wianno
Wianno Vacation Rentals
More Places to Stay Near Osterville

Osterville Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During the Off-Peak Seasons: Visiting outside of peak summer months can help you enjoy a more relaxed atmosphere and better rates at your vacation rental here.
  • Explore Local Waterfront Activities: Take advantage of the region's scenic waterways by engaging in boating, kayaking, or fishing to fully experience the area's natural beauty.
  • Discover Nearby Dining and Shopping Spots: Supporting local eateries and boutiques enhances your stay and offers a more authentic experience of this destination.
  • Book Well in Advance: Secure your preferred vacation rental early to access the best properties and ensure availability during your planned travel dates.

Transportation Options

  • Boston Logan International Airport: You can arrive at this major airport, just a short drive from the area, for convenient access to your vacation rentals.
  • Cape Cod Transit Service: This regional bus service offers reliable transportation around Cape Cod, making it easy to explore nearby towns and beaches.
  • Local Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available within the region, providing flexible transportation during your stay.
  • Private Car Rentals: Renting a car locally grants you the freedom to discover all the scenic spots and hidden gems here at your own pace.

Local Customs Options

  • Community Events and Parades: Participating in local community events and parades is a cherished tradition here, offering an authentic glimpse into the area's close-knit spirit.
  • Cape Cod Souvenirs and Crafts: Supporting local artisans by purchasing handmade crafts and souvenirs helps preserve the region’s artisanal heritage.
  • Seafood Dining Etiquette: Enjoying fresh seafood often involves specific dining customs, reflecting the area's maritime roots and culinary traditions.
  • Respect for Marine Conservation: Visitors are encouraged to observe eco-friendly practices and show respect for marine life, emphasizing the region's commitment to preserving its natural beauty.

Frequently Asked Questions About Osterville?

1. What are the top vacation rentals 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 Vacation Rentals in Osterville:

2. How many vacation rentals have private pools in Osterville?

There are 19 vacation rentals with private pools near Osterville. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Osterville are best for families?

If you are looking for a family-friendly vacation home in Osterville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osterville:

4. How many Rentbyowner vacation rentals are available in Osterville?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 156 in the Osterville area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Osterville. 

5. What is the cancellation policy for vacation rentals in Osterville, Massachusetts?

Cancellation policies vary depending on the specific listing. You should review the cancellation terms listed for each property or contact the owner directly to understand your options and any potential fees.

6. How do I verify the safety and cleanliness standards of a vacation rental here?

Safety and cleanliness standards are typically detailed in the listing description. You can also reach out to the property owner for additional information to ensure the property meets your expectations for a secure stay.

7. Are there any special amenities or features included with vacation rentals in this destination?

Amenities vary across properties, from private pools to outdoor spaces. To find accommodations that suit your needs, review the listing details or contact the owner for specific amenities available during your stay.

8. What are the check-in and check-out procedures for rentals in this region?

Check-in and check-out times are specified in each listing. For any special requests or detailed procedures, it’s best to communicate directly with the property owner before your arrival.

9. Is there support available if I encounter issues during my stay in a vacation rental here?

Support options depend on the individual rental. Most listings offer contact information for the owner or local support services, so reaching out directly ensures a prompt resolution to any concerns during your visit.

Osterville Top Rated Vacation Rentals

See More Osterville Vacation Rentals