Plan your trip

A rocky shoreline with waves crashing onto the beach, a house on stilts, and a forested hillside in the background.

Wading River Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Sign in

  • Be picky

    Search almost a million properties worldwide

  • Find vacation rentals that suit your style

    Cottages

    Apartments

    Condos

    Villas

    Houseboats

    Check prices for these dates

    Check prices for these dates, December 13–14, 2026

    View in a map

    Our top choices for Wading River vacation homes

    1. Cozy beach hose minutes from Hamptons

    A spacious living area with a fireplace, a wooden staircase, and large windows.

    2. Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

    A living room with a sofa, a coffee table, a TV mounted on the wall, and a window with a view of houses outside.

    3. Peaceful 3BR Garden Cottage Long Island Escape

    A garden with a small waterfall, rocks, and statues.

    4. Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

    A two-story house with a front porch, a gravel pathway, and a small garden area.

    5. Jacuzzi year-round - Villa Luz Private Home

    A residential property with a covered patio, outdoor seating, and a hot tub.

    6. Near the Hamptons - Private Pool, Jacuzzi Retreat

    A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

    7. Modern Vacation home. Close to The Hamptons

    A modern kitchen with a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

    8. Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

    A hot tub with two chairs, a pergola, and a wooden deck.

    9. Beachfront Jacuzzi All Year - Black Swan Home

    A modern building with large windows overlooking a beach.

    10. The Royal Suite - Ronkonkoma

    A covered outdoor seating area with a white door, a 'No Smoking' sign, and string lights.

    11. 3 Story Beach Waterview, 3 KING bed, golf putting green!

    A dining area with a table set for four, large windows, and a ceiling fan.

    12. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

    A modern living room with a grey sofa, round coffee table, and a white fireplace.

    13. Stony Brook Village 3BR ranch, fire pit

    A modern kitchen with white cabinetry, a central island, and a dining area with a round table and chairs.

    14. Immaculate Waterfront 2 bedroom!

    A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

    15. Historic Home near Stony Brook Village & Beach

    A living room with a sofa, a coffee table, a mirror, and a patterned rug.

    16. Peaceful private 2-bedroom house in Bayport. Amazing location!

    A modern living room with a grey sofa, a wooden coffee table, a flat-screen TV mounted on the wall, and a ceiling light fixture.

    17. Elegant 5-Bedroom Hamptons Home with Private Pool

    A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

    18. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

    A wooden interior with a staircase, a blue sofa, and a fireplace.

    19. Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras

    A hallway with a white door, a window with a decorative glass design, and a potted plant on a shelf.

    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.

    View all properties

    Learn more about Wading River

    Quiet beaches along Long Island's North Shore invite you to relax with a book or hunt for seashells at low tide. Duck Pond Day festival brings locals together each September with live music, while nearby Wildwood State Park offers scenic hiking trails.

    See all hotels in Wading River

    A rocky shoreline with waves crashing onto the beach, a house on stilts, and a forested hillside in the background.

    Top reviews in Wading River

    The Inn And Spa At East Wind

    An outdoor dining area with tables set for a meal, large windows, and a ceiling fan.

    Hotel Indigo Long Island - East End by IHG

    An outdoor dining area with brick walls, tables, and chairs.

    Holiday Inn Express & Suites Riverhead - Long Island by IHG

    A buffet with various food items, including omelets and baked goods, served in metal trays.

    Danfords Hotel and Marina

    A covered wooden deck with white railings, blue doors, and hanging flower arrangements.

    Holiday Inn Express Stony Brook by IHG

    A breakfast bar with cereal, fruit, and yogurt options.

    Shorewood Inn

    A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

    Seven Beach Lane

    A modern two-story building with a pool area featuring sun loungers and umbrellas.

    Comfort Inn Medford - Long Island

    A hotel lobby with a reception desk, a blue sofa, a flat-screen TV, and a fireplace.

    Explore a world of travel with Expedia