Your comfortable vacation rental in Osterville, Massachusetts locates you in a charming seaside resort that blends small town affability with the sublime scenery of Cape Cod. The beach is never far away in this picturesque village, which is amply served with exciting seasonal events, especially for its size.

Choose the perfect vacation rental
Best Vacation Home Deals in Osterville
Save up to 63%
Find a dreamlike accommodation from $95 per night by searching and comparing the 558 properties listed in Osterville. Each of the properties from our partner websites are directly compared by our algorithm to help you save up to 63%.
Top-Rated Rentals and Accommodations in Osterville
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Recommended Vacation Rentals in Osterville
Find your perfect vacation rental in Osterville: from $95 per night
Budget-friendly Vacation Rentals in Osterville
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Vacation rentals and apartments with air conditioning
Keep cool during your trip to Osterville and book a vacation rental with air conditioning.
Best vacation rentals with a balcony
Looking for a home with a balcony? Check out these vacation homes in Osterville with their own private patios and balconies.
Vacation Rentals With Fireplaces
Get warm and cozy on cold winter nights in Osterville by booking a vacation home with a fireplace.

Popular Rental Amenities in Osterville
Our search page's filters will help you find the ideal vacation rental in Osterville. HomeToGo's data reveals that "Pets allowed" and "Air conditioning" prove to be the most frequently provided features in Osterville. You could even look for rentals if you want a rental with a jacuzzi (20 rentals include "Hot tub" in Osterville) or if you'd like to have a fenced-in yard (44 rentals in Osterville include "Fenced").
The Weather in Osterville
You can see our climate diagram above. During July, maximum temperatures go up to more than 81° Conversely, January is the coolest month in Osterville, with temperatures going under 25° The rainiest month is February while the driest month is August.
7-Day Weather Forecast in Osterville
Accommodations for your vacation in Osterville
Seaside suppers on Cape Cod
In the summer, the farmers' market at Osterville groans heavily with the weight of juicy and delicious produce, grown locally. Come and check out the stalls, which are also packed with homemade cakes, cookies, and other goodies.
The coastal location of Osterville guarantees fresh fish in the restaurants that line the marina too.
Water sports and seasonal festivals
Your whole family will adore sailing in Nantucket Sound, and will love the bike excursions along the coastal pathways.
Boating fans will be enamored of the marina's range of vessels, which you can easily charter and explore the area by sea. Don't miss the seasonal Village Days, which entail floats, food, and live music.
Information about vacation rentals in Osterville
🏡 Vacation rentals available | 558 homes |
---|---|
💳 Possible discounts | up to 63% |
🌙 Nightly prices starting at | $95 |
⭐ Popular amenities | Pets allowed, Air conditioning and Pool |
🐾 Pet friendly homes | 146 homes |
🏊 Vacation rentals with pools | 87 homes |
Frequently Asked Questions
What is the typical price per night for a vacation home in Osterville?
The price of a night's stay in Osterville starts at $95. If you are looking for a house rental, the nightly price is $838 on average. A cabin Osterville will cost on average $539 per night.
How many vacation rentals are available to book in Osterville?
Currently there are 558 rentals in Osterville to choose from and rent for your upcoming trip.
What are the most popular amenities for vacation rentals in Osterville?
Travelers search for Pets allowed, Air conditioning, and Pool when booking a vacation rental in Osterville.
How many vacation homes with a pool are there in Osterville?
There are 87 vacation rentals across 5 providers in Osterville.
Are pets allowed in vacation rentals in Osterville?
If traveling with a pet in Osterville, 26% of vacation rentals allow pets.
What are the best months to travel to Osterville?
When looking for a vacation rental in Osterville, consider that rainy season is typically in February or December, with August often being the driest.
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