Holiday rentals with a home theatre in The Hamptons

Charming 2BR Cottage, Walk to Town

Beech Tree Cottage is a charming 2-bedroom, 1-bath, two-story cottage conveniently located in the peaceful historic district of Sag Harbor, NY. It is a 5-minute walk along the waterfront to Main Street and the center of the village. PLEASE NOTE: We are currently only accepting week- or month-long stays for July and August. We will open up forshort stays in summer subject to availability after May 15. (Short stays are ok in other months.) Please review our house rules before making an inquiry.

New Midcentury-Dream Modern Gym Pool Beach

Welcome to your EH retreat! This 2025 modern renovation combines sleek with sophistication over 5 bedrooms and 3 full baths. Outside enjoy a large fenced backyard with 20x40 pool, loungers, outdoor living room, fire pit, outdoor shower. Inside indulge in hotel comforts—shampoo, conditioner, towels, fresh linens, and robes. Relax in one of the 3 living rooms with big-screen TVs and high-speed WiFi or workout in the full gym w/ sauna. The kitchen has all modern appliances and even includes coffee.

Southampton Village Near Ocean & Shops - Suite "A"

Our suite "A" features location, location, location! You are so close to everything, you can leave your car behind! Just two blocks from historic Main Street. Ocean beach is less than a mile at the end of the road. Brand new lower level apartment. Private entrance. Enjoy sipping wine outdoors in a private sitting area. Off street parking for one car available. Level 2 EV charger w/J1772 plug available for overnight charging. On the premises for use is a heated gunite pool & outside shower.

Moonlit Manor | Shelter Island Escape w/ Sauna

June Dates Available Where design meets relaxation steps from idyllic Hay Beach, Moonlit Manor offers peace, style, and whimsy. Watch songbirds and deer through the picture window, catch a film in the jungle-inspired home theater, or cook in the Jetsons-worthy kitchen. Three bedrooms, a cozy study, private office and a fitness room with Tonal keep comfort and creativity in balance. Outside, garden paths lead to a barrel sauna for four: your private retreat for cool evenings under the stars.

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.

Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open

Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families, friends or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings, games room and movie room. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool (can be heated for a fee).

Hamptons Perfection: salt Pool, Sauna and Location

Situated on a half-acre of land, this classic offers the ideal Hamptons getaway. Located between the picturesque village of Sag Harbor and EH. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 3 bathrooms and heated pool | sauna, & EV Charger offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – Please note there is a basement apt w a seperate entrance w the owner living in that dwelling.

New listing | 50ft Pool on 1.6 Private Acres

NEW LISTING! More than a vacation rental, this is a family home with a story—and a soul. Set on 1.6 private acres along a peaceful country road, it's perfect for walks or jogs to the nearby waterfront. Enjoy a 50' heated saltwater pool, four bikes, a ping-pong table, an authentic saloon piano, and a hidden movie screen. Recently renovated while preserving its character, it's minutes from beaches, wineries, restaurants, and farm stands.

NY Waterfront Home with Private Beach Access

Breathtaking views of the Great South Bay and Fire Island from this updated home sitting on almost two acres of stunning prime waterfront property. The large deck is perfect for relaxing. The property has one of the few natural cut-outs with a path to the water.Near the Fire Island Ferry, Patchogue train station and wonderful restaurants of both Bellport and Patchogue Village as well as the nearby Hamptons and Wineries of Long Island.

East Hampton 3 Bed / 3 Bath Charmer w Pool

Situated on a half-acre of land, this classic shingle cottage with designer interiors offers the ideal Hamptons getaway. Located in the picturesque area of East Hampton, less than 5 miles from town, bay 7 Ocean beaches. 3 bedrooms, 3 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Village Fringe Designer Home

Design-forward East Hampton retreat 5 minutes from the Village and 15 from Sag Harbor. Features vaulted living room, chef’s kitchen with two Bosch dishwashers, whole-house Sonos, stylish bedrooms, two remote-work spaces. Outside: heated saltwater pool, hot tub, 1,900 sq ft of decking, umbrellas, fire pit, Big Green Egg, and EV plug. Basement lounge has projector, 5.1 surround, extra fridge/freezer, and workout area.

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!