Vacation rentals in Ditch Plains

Ditch Plains/ Chic ocean view beach retreat

Private magical 2 acre surf retreat a five min walk to the famed Ditch Plains beach. Nestled on a private road in the best area, this newly renovated airy 3 bedroom, 3 bath has luxurious lawns, sprawling nature, and stylish lounging areas indoors and out. Wolf & Bosch luxury appliances. Tasteful furnishings and linens. Listen to the waves and enjoy sunsets and ocean & lake views from several patios and balconies. Plus Weber BBQ, wi-fi. central A/C & heat, charming outdoor dining area & fire pit.

Ditch Plains Beach Cottage

Super Cute 2 bedroom cottage overlooks nature just 3 short blocks to iconic Ditch Plains beach. New modern bathroom and kitchen connects the front and rear decks and back yard. Rear deck has an outdoor shower. Each bedroom features a queen bed (one bed being a tempurpedic) with Egyptian cotton sheets and down pillows. Both bedroom come with ample closet space. There is a Bose bluetooth sound system, Wifi, Cable and Apple TV. Four bicycles are provided for easy cruising to the beach. RR-25-598

Montauk Surf Cabin with Deck on a Nature Preserve

Relax and enjoy the best Montauk has to offer at this peaceful, comfortable, and stylish cabin. With 4 BR and 2 BA (one en suite in the primary), everyone has space and comfort in this gem of a home. Out back, overlooking the nature preserve, you'll find a large deck with lounge seating, a huge dining table and an ice plunge and sauna. Only about a mile from Ditch, Town and the Dock, at the end of a private gravel road, this unique space is the perfect location for you and your friends or fam.

Atlantic Whispers

Wake up to ocean vistas every morning in a charming cottage. There are stunning views of the waves, soothing ocean sounds, and a gentle sea breeze. Sip coffee on a sun-drenched porch, enjoy a sunset stroll along sandy beaches, or simply unwind with the mesmerizing horizon as your backdrop, this cottage provides the perfect blend of comfort and charm. The cottage features a cozy interior with a working fireplace, modern amenities, and large windows that showcase the stunning seaside scenery.

Cozy Poolside 1 BR in town | Fast WiFi

Enjoy crisp ocean air and stunning pool views from our private terrace, with two heated pools, open for your enjoyment through October 12th! This bright, 5-star coastal retreat features blazing-fast 493 Mbps Wi-Fi and a welcoming dining area that doubles as a comfortable remote workspace. Our railroad-style retreat comfortably fits 4, with queen-sized bed and sofa-bed. Located just steps from the Montauk sand, you can easily walk to both the beach and town for the ultimate autumn escape.

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.

Sea Roost

This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts

6 minute walk to Ditch Plains Beach

IMPORTANT: From Memorial Day 2024 - Labor Day 2024: weekly (1 week/2 week/3 week rentals must start and end on Saturdays. Monthly rentals can start on the first of the month regardless of the day of the week. Great beach house close to Ditch Plains beach with 3 bedrooms and 2 bathrooms. 2 queen beds and 2 bunk beds, deck, barbecue, outside shower, huge yard, recreation room. Spend your days at the beach and grill at night. Wifi, tv, and outdoor fire pit.

Ditch Plains Family Beach House

Sunny 4 bedroom house on a quiet street overlooking a preserve just 3 short blocks to iconic Ditch Plains Beach. Fully equipped kitchen opens out to upstairs deck and grill. There is wifi, cable, central a/c and aloha vibes. Upstairs living room equipped with TV, downstairs set up like a home office. Can bike to beach or town. Rear deck has a spacious outdoor shower. Tankless hot water means no cold showers EVER. East Hampton Rental Registry: 18-371

Sea Ranch At Ditch Plains - Welcome To The Beach

Wake Up To Your Own Private Sea Ranch Retreat — Inspired by the California coastal design belief that human life should live harmoniously with the natural elements of the land & sea. With that we've crafted the perfect hideaway for anyone (you, your friends, the family) to relax / unplug / & enjoy a much needed escape to The End in a space designed to recharge. 4 Bedrooms, 2 Bathrooms, 2 Streets Off Ditch Plains Beach - what more could you need!

Secluded 1Br cottage on the lake, close to Ditch

This is the best of Montauk living, right by the lake, close to Ditch, and with an incredible, lush front yard suitable for outside dining or having a couple friends over for dinner. Walk down to the lake to enjoy the sunset, or stroll over to the Crow's Nest for drinks or dinner. No need to drive, it's well within walking distance. Join the many that have experienced the magic of our cottage at South Lake.

Salt Box in Ditch Plains Montauk

Summer home away from home. Enjoy a view of Lake Montauk as you BBQ and dine on the spacious patio. Just walking distance to the best surf break on the east coast. This traditional salt box style home offers 4 bedrooms, 2 full bathrooms, an outdoor shower and open concept kitchen and living area. The perfect spot to enjoy all Montauk has to offer and make your memories at "The End".