Osterville Vacation Packages

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Your Osterville Vacation

Come and experience this captivating city for yourself with a Osterville vacation package. Consider staying in the neighborhood of Mashpee Neck, which is great for walking and views, and your time here will be nothing short of unforgettable. Ready to start exploring your surroundings? Cape Codder Water Park, Hyannis Harbor and Cape Cod Melody Tent are three of the best places to visit during your trip to Osterville. Whoever you're heading away with and whatever you want to spend, your ultimate Osterville vacation is only clicks away with Expedia.

Top Osterville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyannis Inn

Hyannis Inn

2 out of 5
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Hyannis (HYA)
8.6/10 Excellent! (1,009 reviews)
The staff were so accommodating, friendly. Excellent location. Highly recommend

Reviewed on Aug. 1, 2025

Inn on Main

Inn on Main

3.5 out of 5
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Hyannis (HYA)
10/10 Exceptional! (68 reviews)
Terrific B&B on Cape Cod - super dog friendly and very hospitable! Excellent breakfasts, charming space, and wonderful hosts. It’s a very convenient mid-Cape location, you will not regret booking with them.

Reviewed on May 10, 2025

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Hyannis (HYA)
8.6/10 Excellent! (206 reviews)
Hallways seem to have no A/C and fins up water park was way to hot in there! & also wished the outdoor pool had cooler water … felt like I was in warm bathsm

Reviewed on Aug. 1, 2025

Chapter House

Chapter House

3.5 out of 5
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Hyannis (HYA)
9.2/10 Wonderful! (153 reviews)
Really enjoyed the bar, which was a great spot for a late afternoon drink before dinner

Reviewed on Aug. 2, 2025

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Hyannis (HYA)
9.4/10 Exceptional! (1,004 reviews)
The location was great and in walking distance to everything. The breakfast is almost all pre-packaged food. That was disappointing. The room was ok. I expect extremely clean rooms and was disappointed that when I moved the table and a few items , there were ketchup stains that had not been cleaned. I cleaned it and said nothing to the family. The woman who greeted us the first night was extremely friendly . Her name was Mary😊

Reviewed on Jul. 22, 2025

Ready to book your vacation to Osterville?

 

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Osterville Hotel Deals

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 CA $125 per night from Sep 2 to Sep 3
CA $125
CA $157 total
Sep 2 - Sep 3
includes taxes & fees
6.8/10 (814 reviews)
"Parking was not an issue. Room's were spacious and clean and beds comfortable. There was minimal towels in bathroom and the TV kept freezing up for a second or two at times. The pool towels, when available were very small. The handle on the pool stairs was very wobbly, and pool needs renovating. ..."

Reviewed on Jul. 31, 2025

Hyannis Plaza Hotel
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $285 per night from Aug 28 to Aug 29
CA $285
CA $342 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (1,433 reviews)
"Jon at Moby Dick Pub was an absolute legend."

Reviewed on Aug. 1, 2025

Bayside Resort Hotel
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 CA $253 per night from Aug 24 to Aug 25
CA $253
CA $368 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (238 reviews)
"Great location, spacious rooms, good size pools and a lazy river. It is a restful oasis to retreat to, once you have explored the towns of the cape, including Hyannis, Chatham and Falmouth Great fun and friendly staff."

Reviewed on Jul. 30, 2025

Margaritaville Resort Cape Cod
See all 6,393 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.
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Frequently asked questions

How much does an Osterville vacation package cost?
Offering great value package deals from CA $674 on Expedia, you'll be pleasantly surprised at how much a vacation to Osterville costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Osterville?
To pick up cheap Osterville vacation packages, plan your getaway outside of peak times like public holidays and major events. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Osterville?
To get the most out of your Osterville vacation, we recommend staying for 4 days. Divide your time between visiting Kalmus Beach, Popponesset Beach and other major sights, in addition to exploring neighbourhoods like Sandalwood Village and West Hyannisport. If you've got some time to spare, add a day trip or tour to your Osterville vacation itinerary.
How to find the best Osterville package deals?
Use Expedia's filters to find some terrific Osterville package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Osterville package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book an Osterville vacation as a package?
Expedia vacation 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 usually get a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Osterville vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Osterville?
If you've got your Osterville vacation dates locked in, book as early as you can to score some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Osterville?

  1. Choose your travel dates: What you plan to do in Osterville and your preferred season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Osterville.
  3. Decide how long to go for: Now that you know more about Osterville, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, book the right Osterville vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.