Holiday rentals with breakfast in Northwest Harbor

NEW: Charming East Hampton home w/ POOL!

Welcome to our charming 3 bedroom, 2.5 bath, 1,700+ SF home. Enjoy the heated pool all summer or relax by the fireplace in the fall and winter months. Sunlight shines through two skylights and oversized windows for the beautiful natural light that East Hampton Springs are famous for. We are just a few minutes drive to all EH bay and ocean beaches as well as EH Town and Amagansett Village. Countless restaurants, shops, farmer's markets, vineyards, art galleries, etc. are all very close by!

Family · Location · Layout

Chic, Modern, Family-Friendly Home in East Hampton

This clean, beautiful, well appointed home is the perfect place for your summer (or winter) getaway! With updated appliances and designer furniture, this chic getaway is both fun and sophisticated. Whether you're a family or a small group of friends, you will make wonderful memories swimming in the heated gunite pool, playing badminton in the yard, grilling on the deck or sipping wine on the balcony. Close to the village, and both bay and ocean beaches! Rental Registry Certificate: RR-25-371

Location · Family · Amenities

A Cheerful 2 - Bedroom Cottage

The cottage is the perfect resting spot for travelers. While staying here you can enjoy nature, farms, vinyards, beaches, golfing, and local attractions. We are conveniently located between the North and South Forks of Long Island. We are in walking distance to the Hampton's Jitney. A 2 min drive to the LIE. And just a 40 min drive to the Orient Pt Ferry. We are 30 mins to The Hamptons, and 5 mins to the LIRR. Most importantly we can assure your stay with us will be, peaceful and comfortable.

Family · Location · Wi-Fi

A beautiful 2 BR apt near beach W/hot tube

✨ Luxury Family Retreat | Modern Comfort Near Beach & City ✨ Welcome to your home away from home! This modern, family-friendly getaway is designed for total relaxation and convenience. Enjoy an open floor plan, stylish décor, and all the comforts you need for a peaceful stay. 🏖 6-minute drive to the beach 🚆 3 minutes to the train station 🌇 Close to city attractions 🌿 Quiet suburban neighborhood Come unwind, connect, and recharge — you’ll feel right at home the moment you arrive.

Family · Location · Beach

The Waterfront Suite on the Peconic River 💙

One spectacular suite by the water's edge, specially designed to bring the natural beauty of the Peconic River into a room full of comfort and leisure. Featuring coastal designed furnishings, indulgent fabrics and timeless colors, this second-floor suite overlooking the Peconic River has a relaxing living room, kitchen, dining area, along with a king bedroom, modern bathroom with shower, and an intimate wraparound veranda with cozy outdoor seating to enjoy the panoramic views.

Family · Location · Breakfast

Artists pet friendly apartment and cabin, sauna.

Full apartment with full bathroom 10 minutes to all Hampton towns. Quiet property Walking distance to free SUP boards and canoes and only 2 minute drive to a dog friendly beaches. Extra bedroom is a Cabin in the middle of the property and was a recording studio, now has queen bed, wifi, fridge, micro wave, heat and AC, TV and DVD player but no bathroom. You have your own parking spots, entrance and outdoor dining area and outdoor shower.

Location · Check-in · Access

Casa al Mare Beachfront Retreat with Ocean View

Welcome to Casa al Mare! If you are looking for a place to relax and recharge, look no further. Enjoy this spectacular direct waterfront home while still very close to the city. Yale and downtown New Haven are 15 minutes away. Step out of the glass doors to the patio and walk on the sandy beach! Relax, walk on the sand or swim in Long Island Sound. Stunning water views await you every day.

Family · Value · Outdoor spaces

The Bay & Vine Retreat

Escape to Southold in the heart of North Fork wine country. Steps from vineyards, the bay, and a private beach, this luxury retreat features an heated pool, private dock access, and spacious indoor/outdoor living. Minutes to local farms, seafood markets, water sports, top restaurants, and the charming waterfront village of Greenport — perfect for relaxing coastal getaways year-round.

Location · Family · Outdoor spaces

RENOVATED AND SPACIOUS SUMMER HOME WITH WATER VIEW

Steps from the beach, this beach house is the perfect destination to enjoy beautiful Shelter Island. Recently renovated summer home across a private beach with large windows, and a sizable garden. Ideal for families, couples or single people. There are bikes at the house, a grill, wifi, games, TV and internet, Xbox etc. You wake up to the sound of birds chirping and nature.

Location · Family · Accuracy

The Unhampton

This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!

Location · Value · Sleep quality

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

Value · Location · Pool

Blissful Bridgehampton

If you want to heat the pool, there will be an extra charge. Very private that sits back on a preserve. 20 by 40 gunite pool. Close to the Hampton Classic. 15 minutes to East Hampton, 10 min Southampton. Bridgehampton and Sag Harbor Town is 5 to 7 minutes away.

Value · Family · Getting around