Osterville Oceanfront Vacation Rentals
500 ft²
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $330/Night
For 7 Nights US $2,309
495.14 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Ocean View
- View
US $305/Night
For 7 Nights US $2,133
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $508/Night
For 7 Nights US $3,553
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Ocean View
- Balcony/Terrace
US $494/Night
For 7 Nights US $3,455
1671 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $791/Night
For 7 Nights US $5,535
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
US $381/Night
For 7 Nights US $2,664
3300 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $1,016/Night
For 7 Nights US $7,110
3500 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,974/Night
For 7 Nights US $13,820
2700 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $384/Night
For 7 Nights US $2,691
3000 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $818/Night
For 7 Nights US $5,728
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $793/Night
For 7 Nights US $5,551
1500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $602/Night
For 7 Nights US $4,217
Why Choose Rent By Owner for your Osterville Oceanfront Vacation Rentals?
What makes our Oceanfront Vacation Rentals 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 Oceanfront Vacation Rentals stay?
Timing your visit to this charming coastal area is essential to fully enjoy the tranquility and natural beauty, with the best months for oceanfront rentals typically falling during the late spring through early fall when the weather is warm and inviting.
Peak Season Highlights
Summer (June to August)
During the peak summer months, this coastal destination experiences warm weather ideal for enjoying oceanfront rentals and outdoor activities.
Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
Early Fall (September to October)
The early fall brings pleasant temperatures and fewer crowds, making it a lovely time to explore the region's scenic oceanfront rentals and serene beaches.
Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
Off-Season Highlights
Late Fall to Early Winter (November to December)
As the area transitions into cooler weather, you can find more tranquil oceanfront rentals and enjoy the peaceful seaside atmosphere.
Average Temperature Daytime: 50-55°F - Nighttime: 40-45°F
Winter (January to February)
The quiet winter months offer a unique experience with fewer visitors and cozy accommodations along the coast, perfect for those seeking solitude.
Average Temperature Daytime: 30-40°F - Nighttime: 25-30°F
Weekly Weather Forecast for Osterville
How to Book Your Osterville Oceanfront Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of oceanfront 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
Common Oceanfront Vacation Rentals Amenities
What amenities can you expect?
Our Oceanfront 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 direct access to scenic beaches with outdoor seating areas perfect for relaxing by the water.
- Take advantage of spacious outdoor patios or decks ideal for al fresco dining and entertaining guests.
- Make the most of lush, private gardens that provide a tranquil setting for outdoor leisure.
- Benefit from outdoor showers to rinse off after a day spent at nearby beaches or exploring the area.
- Utilize well-maintained barbecue grills for enjoying cookouts with ocean views.
- Relax in outdoor lounge chairs or hammocks designed for soaking up the sun amidst natural beauty.
- Practice outdoor activities such as kayaking or paddleboarding with convenient storage or launching spots on site.
Top Attractions Around Osterville
What attractions are nearby?
Explore a variety of enjoyable activities nearby, from charming waterfront strolls and boating adventures to exploring local shops and dining options, all within close proximity when you stay in this destination's scenic oceanfront rentals that offer the perfect setting for relaxation and adventure.
Family Activities
- Wianno Golf Course Enjoy a family-friendly round at this scenic golf course known for its beautiful views and relaxed atmosphere, perfect for introducing kids to the sport.
- Millway Beach Spend a day relaxing or building sandcastles on this tranquil beach, offering safe swimming areas ideal for families seeking an oceanfront experience.
- Trails at Osterville Village Green Explore the charming village green with its walking paths and local spots, providing an enjoyable outdoor activity for all ages.
- Osterville Historical Society Museum Discover the area's rich history through interactive exhibits and family-friendly tours that bring the region's past to life.
Adult Activities
- Bird Watching Tours Discover the region’s diverse avian species on guided bird watching excursions that cater to all levels of enthusiasts.
- Fishing Charters Embark on a fishing adventure along the coast, where local charters offer an authentic experience in the area’s prime fishing waters.
- Kayaking and Paddleboarding Explore the calm waters and scenic shoreline by renting kayaks or paddleboards, perfect for both relaxation and outdoor exercise.
- Historical Harbor Walks Take a leisurely stroll through the historic waterfront, learning about the area's maritime heritage while enjoying picturesque views.
Other Places to Stay in Osterville, MA
Dowses Beach
Stand Up & Paddle Cape Cod
Public Beach
Wianno
Osterville Travel Tips
How Can You Make the Most of Your Stay?
- Explore the local waterways: Take advantage of the proximity to the water by booking activities such as kayaking or paddleboarding to fully enjoy the scenic oceanfront surroundings.
- Visit nearby beaches: Make the most of your stay by spending time on the region's beautiful beaches, ideal for relaxing, sunbathing, and soaking in the coastal atmosphere.
- Dine at local seafood restaurants: Savor fresh, locally caught seafood at nearby eateries to experience authentic regional flavors during your visit.
- Plan outdoor excursions: Discover the area's natural beauty through outdoor activities like walking along scenic trails or visiting protected coves, perfect for unwinding and connecting with nature.
Transportation Options
- Driving Renting a car offers flexibility to explore the picturesque coastline and nearby attractions at your own pace, making it an ideal option for accessing oceanfront rentals in this charming region.
- Public Transportation The regional bus service provides convenient access between key locations here, allowing you to enjoy the area's scenic views without the hassle of driving.
- Taxi and Rideshare Services On-demand taxi and rideshare options like Uber or Lyft are readily available, offering a reliable way to navigate around this destination comfortably and efficiently.
- Bike Rentals For a more active approach, bike rentals allow you to traverse coastal pathways and explore the area’s natural beauty while enjoying the fresh ocean air.
Local Customs Options
- Clam Baking Tradition: Participating in or observing a traditional clam bake is a cherished custom that highlights the area's maritime heritage and local flavors.
- Seasonal Lobster Celebrations: The region celebrates its connection to fresh seafood with seasonal lobster festivals and gatherings that showcase regional culinary traditions.
- Saltwater Beach Etiquette: Respectful beach practices, such as keeping the shoreline clean and observing quiet hours, are important customs here, especially at popular coastal spots.
- Local Craftsmanship: Supporting handcrafted goods and art, often inspired by the surrounding landscape, is a common way residents honor their cultural roots in this destination.
Osterville Oceanfront Vacation Rentals Frequently Asked Questions
1. What are the top Oceanfront 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 Oceanfront Rentals in Osterville:
- Heated Private Pool, Walk to beach & shops, fully renovated house
- Spectacular waterfront home/boat dock Indoor & Outdoor pool
- Pristine Osterville Cottage
- Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass
- Charming 4BR Osterville Home, Walk to Pond, 2 mi to beach, Hot Tub & Beach Pass
- Osterville Escape to our Spacious Family Getaway. Barnstable Beach pass included
- An Osterville Gem!Very close to town and beach!
- Beautiful designed, newly constructed home- all the amenities, close to beaches
- Swing Set, Plunge pool, and large yard await!
- Amazing Beautiful Osterville, Cape Cod, MA! Beach Pass, Fire Pit, Sleeps 10
2. How many Oceanfront Rentals are available in Osterville?
Currently, the total number of properties listed by RBO in 2026 is over 102 in the Osterville area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in Osterville.
3. What is the cancellation policy for oceanfront rentals in Osterville, Massachusetts?
The cancellation policy varies by listing. You should review the specific rental terms on the property’s page or contact the property owner directly to understand the applicable cancellation and refund options.
4. Are there any additional fees I should be aware of when booking an oceanfront rental here?
Additional fees such as cleaning, security deposits, or service charges are detailed in each listing. Be sure to read the full property description or reach out to the owner for clarification before confirming your reservation.
5. What amenities are typically included with oceanfront rentals in this area?
Most properties include essentials like Wi-Fi, parking, and kitchen facilities. Some may offer extras such as outdoor decks, private access to the water, or beach gear. Check the property details for a complete list of amenities available during your stay.
6. How do I secure my reservation at an oceanfront rental in this region?
Reservations are generally confirmed through the booking platform after you select your dates and provide payment details. For specific instructions or assistance, contact the property owner directly via the listing or customer support.
7. Is it possible to modify or cancel my reservation for an oceanfront rental once booked?
Modification and cancellation policies depend on the individual listing. Review the rental terms carefully or contact the owner to discuss flexible options and ensure your plans can be adjusted if needed.
More Rentals You May Like Near Osterville
10 Guests
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Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,379/Night
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3988 ft²
12 Guests
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20 Guests
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US $2,749/Night
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9 Guests
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- Ocean View
- Balcony/Terrace
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US $1,302/Night
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6 Guests
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Ocean View
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- Ocean View
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US $1,354/Night
For 7 Nights US $9,476
8 Guests
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Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
US $956/Night
For 7 Nights US $6,695
12 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $5,796/Night
For 7 Nights US $40,572
9 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $854/Night
For 7 Nights US $5,976
6 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $667/Night
For 7 Nights US $4,669
2171 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $620/Night
For 7 Nights US $4,340
12 Guests
6 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $4,838/Night
For 7 Nights US $33,867
2758 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $1,185/Night
For 7 Nights US $8,292
