Holiday rentals with breakfast in Shelter Island Heights

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 · Wi-Fi

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 · Kitchen

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.

Location · Family · Amenities

POOL + Beach Oasis! Winter deals 2+ nights!

Chef kitchen: 2 ovens/lux app's/coffee bar w/ Nespresso/Keurig 2 living rooms Dining room seats 10 1st floor Primary Suite: king bed, gas fireplace, furnished deck overlooking pool, 4 piece bath: huge shower & jacuzzi tub 2 of 4 Guest rooms on 1st fl Gym/yoga rm: bench + weights (no treadmill) TV's in bedrooms inc. Firesticks Fenced backyard oasis w/ heated mineral spring pool, loungers, shaded cabana, outdoor dining, & Weber BBQ, outdoor shower Kitchenette in den/office Central AC/heat/fans

Location · Family · Backyard

Beautiful Hampton Home, 4 bedroom, heated pool

Beautiful Hampton 4 bedroom, 3 1/2 bath home, with heated pool, outdoor shower, located on one acre,in beautiful upscale neighborhood ,located on quiet cul-da-sac street.Close to Sag Harbor town and beaches. Large 65" TV in huge Cathedral main living room. 65" TV also in large separate den with treadmill. King Size bed on 1St floor with 2 beds next door. New large Spa bathroom on 1st floor. King Size Master bedroom 2nd floor,50"TV ,and en-suite bathroom. 2 beds in add bedroom, with en-suite

Family · Location · Pool

A 1 BR Luxury Apt to relax w/hot tube

Experience relaxation and style in this luxurious, With modern décor and an open floor plan, this serene retreat offers the perfect “home away from home.” Located just 3 minutes from the train station and a 6-minute drive to the beach, you’ll enjoy the best of both worlds. Unwind in the spacious living area. Whether you’re traveling with family or friends, this space makes quality time effortless. Escape, explore, and enjoy — your perfect getaway awaits. https://www.airbnb.com/l/omZEnqfH

Value · Location · Hot tub

Modern Hamptons Home

Escape to a beautifully renovated Hamptons retreat designed for comfort, privacy, and effortless outdoor living. Enjoy a spacious deck and private fenced backyard featuring a unique outdoor lounge, BBQ grill, fire pit, and refreshing outdoor shower. Inside, bright and stylish spaces offer all the comforts of home. Perfect for relaxing, dining outdoors, and creating memorable moments with family and friends, all while being conveniently located near beaches, restaurants, shopping, and local.

Value · Location · Parking

Summer Cottage

Cottage in Roses Groves, Southampton, NY. Great location to avoid traffic on 27. Cottage has access to a private beach on the Peconic Bay (5 min walk). 15 min drive to ocean beaches in Southampton, and Southampton village. 10 min drive to Watermill, 20 min to Sag Harbor and BH. A farm and a deli are less than a mile away. Two restaurants nearby Perfect for artists, ocean lovers, book lovers and families. A/C in living room and bedrooms. Located on a quiet street, very relaxing

Value · Family · Walkability

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.

Location · Value · Wi-Fi

Sag Harbor Beach Cottage

Quaint, clean beach cottage with designer gardens that offer privacy. Conveniently located 2 1/2 blocks from Circle beach and Hidden Cove Marina, it is a short drive into downtown Sag Harbor and a 1/4 mile walk to Trout Pond. and nature trails. Up the street we have a grocery store, liquor store, restaurant and deli. Kayak rentals nearby. Outdoor shower with hot water for rinsing off and a gas grill for outdoor dining. Central AC/Heating system.

Family · Value · Sleep quality

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 · 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 · Biking