Osterville Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Osterville

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is 3.977.467 ₫ per night from 14 Sept to 15 Sept
3.977.467 ₫
6.057.703 ₫ total
14 Sept - 15 Sept
includes taxes & fees
8.6/10 Excellent! (291 reviews)
"Very family friendly, great pool, multiple fire pit for roasting marshmallows, indoor heated water park, arcade games. There is a cafe, a gift shop, a bar and restaurant with a door and out in the center of the resort where there is fire piths, a ballroom inside for free dance lessons. There is free ..."

Reviewed on 23 Aug 2025

Margaritaville Resort Cape Cod
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is 3.919.594 ₫ per night from 2 Sept to 3 Sept
3.919.594 ₫
4.880.552 ₫ total
2 Sept - 3 Sept
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"The owners were having a problem with the hot water that/day/evening. They were super apologetic even though we did not mind( if taking a cold shower is gonna ruin my day-I’ve got issues). Everything was turned back on by 7:00 pm. Contractor looked like he had been run over by a truck he was so tired. ..."

Reviewed on 24 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! (1,485 reviews)
"We had a great 5 night stay . Bay view room great access to pool and kitchen below. The included breakfast worked out great . Our room service was great we will definitely stay again ."

Reviewed on 22 Aug 2025

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Bayside Resort Hotel
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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.

Popular places to visit

Stand Up & Paddle Cape Cod

Take the family on an outing to Stand Up & Paddle Cape Cod during your trip to Osterville. Attend a sporting event or simply enjoy the seafood restaurants while you're in the area.

Stand Up & Paddle Cape Cod

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.