Family-friendly holiday rentals in Napeague

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway. (No AI used in these photos!)

Montauk Beach Bungalow East Apt.

Charming, clean, private, quiet, 2 bed 1 bath ocean view apartment across from ocean beach via through dunes path. Check the surf from the living room window. Dine in or out with the moon rising over the ocean. Includes BBQ and fire pit, outside table. Private entrance, lawn, outdoor shower, storage space for bikes, etc. Perfect vacation rental. Full kitchen with stove oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc - monthly discounts. Small bathrm & shower

Modern Montauk retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy, all-season getaway with open-plan interior & large, private fenced yard. • 950 sq ft, 2 BRs (compact but comfy), 1 Ba, full high-end kitchen, W/D, A/C • Wood stove, Solo stove, patio, outdoor shower, high-end linens & furnishings/decor • Steps to LI Sound & Harbor. 3 mi to ocean/Town • Owner is in a private studio w/ own entrance in the house. No shared spaces! • Ask about dogs & flexible rental periods CLICK MORE for IMPORTANT INFO!

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.

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Sunny & Serene Private Cottage near Downtown EH

Our lovely one-bedroom cottage sits on a quiet lane 3/4 of a mile from downtown East Hampton. The cottage is light and bright, with whitewashed walls, vaulted ceilings and skylights, lots of windows and beautiful minimalist décor. It's an incredibly peaceful place to wake up in the morning, with a gorgeous green yard right outside the many bedroom windows. Every bay and ocean beach around East Hampton is 5-10 minutes away and Nick and Toni's is less than a 10 minute walk.

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

MONTAUK OCEAN FRONT!

Charming oceanfront Montauk locale with perfect proximity to all town activities! Fall asleep to the lull of ocean waves. Ocean view and steps to the sand and town! New kitchen, Queen bedroom,Queen sofabed in living area, new rain shower bathroom, plus a large front deck for al fresco dining! Perfect for families, and a girls weekend!

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.