Oyster Bay Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Oyster Bay Vacation
Reserve a Oyster Bay vacation package that includes everything you need and no unnecessary extras. Great for views, cafes and watersports, consider staying in the neighborhood of Waikawa Bay. Te Weu Weu Bay is one of the must-see attractions to include on your sightseeing agenda during a trip to Oyster Bay. Whoever you're heading away with and whatever you plan to spend, your ultimate Oyster Bay vacation is only clicks away with Expedia.
Ready to book your vacation to Oyster Bay?
Oyster Bay Hotel Deals
Harbour View Motel
30 Waikawa Road Picton
CA $99
CA $114 total
Sep 28 - Sep 29
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Thetwo bedroom apartment is wellappointed with a good lookout. The tableand and balcony, leading onto the grassy shared seating area, is clever. The apartment layout is good and having the bedrooms down stairs is also a good layout. The shower unit is perhaps in need of perhaps some renovation however ..."
Reviewed on Sep 8, 2026
Edit Picton
25 Waikawa Road Picton
Fully refundableReserve now, pay when you stay
CA $74
CA $85 total
Sep 20 - Sep 21
includes taxes & fees
8/10 Very good! (1,001 reviews)
"The furniture and fixures were poor at best. It was dark in the room in various areas as there were 4 x lights not working. The kitchen was very poorly lit for a work space. Staff attitude was uninterested . Breakfast was 1.5 star -- bad cafe level. Barely $10 -not $30 worth. The lounge looked like ..."
Reviewed on Sep 9, 2026
Picton Beachcomber Inn
27 Waikawa Road Picton
Fully refundableReserve now, pay when you stay
CA $78
CA $90 total
Sep 30 - Oct 1
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"The property was located approximately 200metres from bars and restaurants and was on the main road to the picton ferries. We had a fabulous view of the harbour and marina. Parking wasn’t an issue. Will stay here again"
Reviewed on Sep 10, 2026
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 Oyster Bay vacation package cost?
You'll find cheap prices on Expedia for your Oyster Bay break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Oyster Bay costs.
What are the cheapest months to go to Oyster Bay?
If you're looking to book a cheap Oyster Bay vacation package, consider visiting in May, June and July. You'll usually find better rates on hotels and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Oyster Bay?
Usually, a handful of days is enough to tick off the main sights during your Oyster Bay vacation. But if you want to have more time to relax or take day trips, think about extending your trip.
How to find the best Oyster Bay package deals?
Use Expedia's handy filters to find some fabulous Oyster Bay package deals. When you begin 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 break for midweek, or search for Oyster Bay package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book an Oyster Bay vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging stays and flights separately. Better still, you can customize your Oyster Bay escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Oyster Bay?
Land amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Oyster Bay vacation.
How to plan a trip to Oyster Bay?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Oyster Bay.
- Set your budget: Factor in expenses like flights, food and transportation when calculating how much to set aside for your trip to Oyster Bay. Then, choose a hotel that works with your budget, whether that's a wallet-friendly option or a deluxe retreat.
- Decide your trip length: Consider how much time you want to spend exploring Oyster Bay. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
- Bundle your airfare and accommodations: Once you've settled on your dates and duration, book the ideal Oyster Bay 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.
