Osterville Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Osterville

Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
662 Main Street, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is S$139 per night from 4 Sept to 5 Sept
S$139
4 Sept - 5 Sept
includes taxes & fees
6.8/10 (826 reviews)
"Great place"

Reviewed on 5 Aug, 2025

Hyannis Plaza Hotel
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
The price is S$213 per night from 2 Sept to 3 Sept
S$213
2 Sept - 3 Sept
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"Restaurant new looks good!"

Reviewed on 3 Aug, 2025

Falmouth Inn
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,447 reviews)
"Good price for the busy summer time . Kids loved the arcade and both pools. Breakfast was great as well!"

Reviewed on 4 Aug, 2025

Get rates
Bayside Resort Hotel
See all 6,375 properties in Osterville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does an Osterville holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Osterville costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Osterville?
The off-season is the best time to visit Osterville if you're trying to keep costs down. Another tip for finding cheap Osterville holiday packages? Try to avoid public holidays and any major festivals or events.
How many days is enough for Osterville?
The ideal duration for your Osterville holiday depends on what you'd like to do. Usually, a handful of days to a week will give you time to visit all the main attractions and explore some hidden treasures along the way.
How to find the best Osterville package deals?
Begin your search for an Osterville package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Osterville package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Osterville adventure underway.
Is it cheaper to book an Osterville holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Osterville holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Osterville?
If you're considering a spontaneous Osterville holiday, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Osterville?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Osterville.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodation will likely be the largest expense during your trip to Osterville.
  3. Decide how long to go away for: Now that you know more about Osterville, you can figure out the ideal length of your break. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose an Osterville holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.