Family-friendly vacation rentals in Aquebogue

4.98 out of 5 average rating, 184 reviews

Quiet Canoe Lake Cottage getaway

Peaceful private home on lush green resort like compound with historical outbuildings plus an additional studio apartment available for larger groups.Ideal for couples or a small family looking to explore the North or South forks of Long Islands East End and a short drive to the Hamptons famous beaches, villages and restaurants.A true garden lovers getaway with extensive flowers, vegetable and fruits and even our own apiary providing local raw honey. Near lots of wineries, restaurants and 2 miles from Tanger outlet mall shopping & top 5 rated Splish Splash Water Park. .Adjacent to the Peconic River for canoeing, kayaking, fishing or birding. The quiet winding country roads on either side of the river are a favorite destination for walking/joggers, biking and motorcycle touring. Riverhead town is a great central location and an easy drive to bay and ocean beaches. The area is still very much a rural farming area and a foodies delight with many pick your own fields,farmers markets, farm stands, wineries, horse, buffalo, and goat farms and even a potato vodka distillery and tasting room! We have an awesome Aquarium in town and our newly reopened Suffolk Theater with nightly live music and shows. Riverhead has lots of inexpensive small cafe style eateries for those on a budget.

4.95 out of 5 average rating, 111 reviews

Walk to Vineyards, Beach, Restaurants • Sleeps 8

• Spacious 3 BR house in heart of Jamesport - includes King, Queen & 2 twin beds. Queen air mattress also available. • Great for family vacations, weekend getaways & local weddings. • Clean sheets, pillows, fresh towels & toiletries. • Backyard complete w/ outdoor bbq, fire pit, hammock & patio seating. • Cook in open kitchen fully equipped w/ dishes, utensils, spices, pots & pans; eat local ingredients from nearby farms & markets. • Indoor & outdoor dining tables seat up to 8 guests.

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Apartment in Ridge

4.74 out of 5 average rating, 166 reviews

The Silver Pine Cone

Welcome to the hamlet of Ridge. The gateway to Long Islands many treasures. Whether you are venturing out to the North Fork wineries or a scenic drive on the south shore beaches on your way to the Hamptons. A beautiful cozy private (not a shared space) full one bedroom downstairs lower level apartment, living room w/full size sofa sleeper, kitchen/dining room, full bathroom and a completely separate yard with patio furniture exclusively for your use. Everything you need to enjoy your stay.

4.96 out of 5 average rating, 194 reviews

Cottage in The Hamptons

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

4.97 out of 5 average rating, 159 reviews

Cottage in North Fork

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

4.98 out of 5 average rating, 166 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

4.97 out of 5 average rating, 151 reviews

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.95 out of 5 average rating, 135 reviews

Home in The Hamptons

Luxury 5BR Hamptons Stay • Close to Beaches

🌟 Rated 4.95 with 130+ glowing reviews – book with confidence! Escape to this stylish 5BR retreat in Hampton Bays—minutes from beaches, dining, and shops. Enjoy open living, a finished basement with ping pong and gym, plus a spacious backyard for relaxing or entertaining. Perfect for families or groups, this modern home offers comfort, convenience, and Hamptons charm near top beaches and attractions. Includes fast WiFi, Smart TVs, BBQ grill & beach gear for the perfect stay

4.86 out of 5 average rating, 107 reviews

Cabin in North Fork

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

4.96 out of 5 average rating, 140 reviews

Guesthouse in North Fork

Walk to Beautiful Beach in Heart of Wine Country

Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.

4.93 out of 5 average rating, 116 reviews

Apartment in North Fork

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!