Oyster Bay Vacations

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Find the Best Oyster Bay Vacation Packages

Oyster Bay Hotel Deals

Edit Picton

Edit Picton

3.5 out of 5
25 Waikawa Road Picton
Fully refundableReserve now, pay when you stay
The price is ￥11,002 per night from Nov 9 to Nov 10
￥11,002
￥12,703 total
Nov 9 - Nov 10
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Great affordability, clean, well-equipped"

Reviewed on Oct 28, 2026

Edit Picton
The Boathouse Lodge

The Boathouse Lodge

2 out of 5
9 Auckland St Picton Marlborough
Fully refundableReserve now, pay when you stay
The price is ￥7,249 per night from Nov 18 to Nov 19
￥7,249
￥8,387 total
Nov 18 - Nov 19
includes taxes & fees
8.6/10 Excellent! (229 reviews)
"."

Reviewed on Oct 21, 2026

The Boathouse Lodge
Harbour View Motel

Harbour View Motel

4.5 out of 5
30 Waikawa Road Picton
The price is ￥16,587 per night from Nov 2 to Nov 3
￥16,587
￥19,075 total
Nov 2 - Nov 3
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Staying one night as catching the ferry but super view and close to the local irish bar!!"

Reviewed on Oct 30, 2026

Harbour View Motel
See all 139 properties in Oyster Bay
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 getaway. However, factors like the hotel choice, length of stay and season will influence 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 traveling in May, June and July. You'll typically find better prices on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Oyster Bay?
The ideal duration for your Oyster Bay vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to tick off all the major attractions and explore some hidden treasures along the way.
How to find the best Oyster Bay package deals?
Begin your search for an Oyster Bay package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Oyster Bay package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oyster Bay adventure underway.
Is it cheaper to book an Oyster Bay vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component individually. And you'll still get the freedom to create a personalized Oyster Bay vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Oyster Bay?
If you're considering a spur-of-the-moment Oyster Bay vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Oyster Bay?

  1. Choose when to go: Check your schedule and pack your bags. Your preferred season and the activities on offer will also help you decide when to escape to Oyster Bay.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and meals to experiences and flights. Your hotel will likely be the largest expense during your trip to Oyster Bay.
  3. Determine how many days away: Start by compiling a list of the attractions and activities you'd like to get to in Oyster Bay. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodations and airfare: Once you've nailed down your travel 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.