An aerial view of a coastal area with a clear demarcation between land and water, a sandy beach, and a distinct shoreline.

Oyster Bay Vacation Packages

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  • Your Oyster Bay Vacation

    When a break in the city is calling, answer it with a Oyster Bay vacation package. The neighborhood of Cove - East Side - Shippan, which is good for cycling, coastal beaches and walking, makes a wonderful base for your adventures. If your trip to Oyster Bay includes a little sightseeing, check out popular attractions like Sagamore Hill National Historic Site, Long Island University Post Campus and Cold Spring Harbor Laboratory. Whoever you're escaping with and whatever you want to spend, your dream Oyster Bay vacation is just clicks away with Expedia.

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    A large, historic house with a red brick porch and a covered front porch area.

    Photo by Henry Tovmassian

    Sagamore Hill National Historic Site

    Rating: 8.8/10 (20 reviews)

    Learn about the local history of Cove Neck when you take a trip to Sagamore Hill National Historic Site. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

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    A grove of cherry blossom trees with pink flowers.

    Planting Fields Arboretum State Historic Park

    Rating: 9.2/10 (7 reviews)

    Take the family on an outing to Planting Fields Arboretum State Historic Park during your trip to Upper Brookville. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

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    A beach with people, a large yellow duck sculpture, and a clear sky with clouds.

    Photo by Erick

    Theodore Roosevelt Memorial Park

    Rating: 10.0/10 (2 reviews)

    Explore the great outdoors at Theodore Roosevelt Memorial Park, a lovely green space in Oyster Bay. While in this family-friendly area, you can savor the top-notch restaurants.

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    Theodore Roosevelt Sanctuary and Audubon Center

    Rating: 10.0/10 (2 reviews)

    You can take time to visit Theodore Roosevelt Sanctuary and Audubon Center during your travels to Oyster Bay Cove. Wander the picturesque gardens in this quaint area.

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    20th Century Cycles

    Rating: 10.0/10 (2 reviews)

    You can browse the exhibits at 20th Century Cycles, a museum with a storied past, during your travels to Oyster Bay. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

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    Beekman Beach

    Rating: 8.0/10 (2 reviews)

    Why not spend a lazy afternoon at Beekman Beach during your trip to Oyster Bay? While you're in the area, wander around the natural setting.

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    What to do in Oyster Bay

    Private Long Island Sound Sailing Experience

    Private Long Island Sound Sailing Experience

    CA $919

    per traveller

    0% of travellers recommend

    Captain Steve sails a Beneteau 343

    Captain Steve's Sailing Experience on Long Island

    CA $776

    per traveller

    0% of travellers recommend

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    Oyster Bay Hotel Deals

    East Norwich Inn

    A hotel hallway with wooden flooring, framed artwork on the walls, and potted plants.
    • Address: 6321 Northern Blvd., East Norwich, NY, 11732, US
    • Location: 3.4 km from Oyster Bay
    • Star rating: 2.5/5
    • Guest rating: 8/10 (Very good, 1807 reviews)
    • Price: CA $169, CA $194 total, includes taxes & fees, Nov 17 - Nov 18

    Hampton Inn & Suites Huntington Downtown

    A brick building with a grand entrance, large columns, and a fire pit in the center.
    • Address: 227 Main Street, Huntington, NY, 11743, US
    • Location: 8.9 km from Oyster Bay
    • Star rating: 2.5/5
    • Guest rating: 9.2/10 (Wonderful, 556 reviews)
    • Price: CA $254, CA $291 total, includes taxes & fees, Dec 14 - Dec 15
    • Review: Been there a couple times very accommodating staff

    SureStay Plus by Best Western Woodbury Inn

    A spacious living area with a sofa, a glass coffee table, and a dark armchair. There is a kitchen visible in the background with wooden cabinets and a countertop.
    • Address: 7940 Jericho Tpke, Woodbury, NY, 11797, US
    • Location: 7.9 km from Oyster Bay
    • Star rating: 2.5/5
    • Guest rating: 7.4/10 (Good, 1001 reviews)
    • Price: CA $134, CA $150 total, includes taxes & fees, Nov 30 - Dec 1

    Viana Hotel and Spa, Trademark Collection by Wyndham

    A hotel lobby with a reception desk, blue chairs, a chandelier, and a staircase leading to the upper floors.
    • Address: 3998 Brush Hollow Rd, Westbury, NY, 11590, US
    • Location: 11 km from Oyster Bay
    • Star rating: 4/5
    • Guest rating: 9/10 (Wonderful, 1033 reviews)
    • Price: CA $265, CA $296 total, includes taxes & fees, Nov 23 - Nov 24
    • Review: Great place and will visit again.

    The Inn At Fox Hollow Hotel

    A restaurant with a stone fireplace, multiple tables, and chairs. There are two visible exits and a television on the wall.
    • Address: 7755 Jericho Turnpike, Woodbury, NY, 11797, US
    • Location: 7.6 km from Oyster Bay
    • Star rating: 4/5
    • Guest rating: 9.2/10 (Wonderful, 1005 reviews)
    • Price: CA $384, CA $429 total, includes taxes & fees, Dec 13 - Dec 14
    • Review: Great for a date night getaway . Staff was kind and helpful. Would definitely stay again.

    Hilton Garden Inn Roslyn

    A hotel room with a bed, desk, chair, and a painting on the wall.
    • Address: 3 Harbor Park Drive, Port Washington, NY, 11050, US
    • Location: 12.8 km from Oyster Bay
    • Star rating: 3.5/5
    • Guest rating: 9.2/10 (Wonderful, 1000 reviews)
    • Price: CA $205, CA $229 total, includes taxes & fees, Nov 22 - Nov 23

    Best Western Premier Plainview-Long Island Hotel

    A room with a large window, two chairs, and a fireplace.
    • Address: 333 S Service Rd, Plainview, NY, 11803, US
    • Location: 12.1 km from Oyster Bay
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 236 reviews)
    • Price: CA $224, CA $251 total, includes taxes & fees, Dec 7 - Dec 8
    • Review: Good hotel!

    Holiday Inn Plainview-Long Island by IHG

    A greenhouse venue with tables, chairs, and floral decorations.
    • Address: 215 Sunnyside Blvd, Plainview, NY, 11803, US
    • Location: 10 km from Oyster Bay
    • Star rating: 3/5
    • Guest rating: 8/10 (Very good, 1005 reviews)
    • Price: CA $177, CA $197 total, includes taxes & fees, Dec 13 - Dec 14

    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 Oyster Bay vacation package cost?

    You'll find cheap prices from CA $1,126 on Expedia for your Oyster Bay escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Oyster Bay costs.

    What are the cheapest months to go to Oyster Bay?

    Plan your trip for the off-season and you're likely to find cheap Oyster Bay vacation packages. Keep in mind that school vacation periods and local events and festivals can have an impact on prices, so do a little research before booking.

    How many days is enough for Oyster Bay?

    For your Oyster Bay vacation, a handful of days will be enough to see the top spots. Make sure to stop by Stehli Beach — it's one of the top attractions in this destination. If you're looking for more adventure, consider basing yourself here and going on some day trips from Oyster Bay.

    Is it worth booking a vacation package to Oyster Bay?

    Oyster Bay offers everything you need for an amazing escape. Get your Oyster Bay vacation off to a flying start by visiting popular attractions like Theodore Roosevelt Sanctuary and Audubon Centre.

    How to find the best Oyster Bay package deals?

    Use Expedia's handy filters to help you find some unbeatable Oyster Bay package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Oyster Bay package deals in the off-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 well in advance.

    Is it cheaper to book an Oyster Bay vacation as a package?

    An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays individually. Better still, you can customize your Oyster Bay trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.

    When to book a vacation package to Oyster Bay?

    If you're planning a spur-of-the-moment Oyster Bay adventure, check out 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 find sensational deals on your hotels and flights by booking ahead.

    How to plan a trip to Oyster Bay?

    1. Pick your travel dates: The things you'd like to do in Oyster Bay and your preferred season will help you decide when to travel.
    2. Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Oyster Bay. Then, pick a property that fits your budget, whether that's a low-cost option or a swankier retreat.
    3. Decide how long to go for: Now that you're up to speed on Oyster Bay, you can work out the ideal length of your vacation. Create a draft plan and give yourself enough time to cover everything you want to do.
    4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick an Oyster Bay vacation package that brings all your bookings together.

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