Vacation rentals in Ditch Plains

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Top-rated vacation rentals in Ditch Plains

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Superhost

A bright sitting area features a white shiplap ceiling with exposed beams. A light-colored sofa is adorned with decorative pillows, positioned near a coffee table. A telescope is placed by a window, offering views of the lush outdoor greenery visible through the glass doors.

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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.

4.91 out of 5 average rating, 35 reviews

Guest favorite

Home in Montauk

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

4.84 out of 5 average rating, 38 reviews

Top guest favorite

Home in Montauk

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.

4.91 out of 5 average rating, 11 reviews

Superhost

A bright studio cottage features a spacious bed with light linens and a working fireplace. A round table with two white chairs sits on a soft area rug, while a blue accent chair is positioned in the corner. Soft light enters through large windows.

Bungalow in Montauk

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.

4.9 out of 5 average rating, 672 reviews

Top guest favorite

Condo in Montauk

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.

5.0 out of 5 average rating, 98 reviews

Top guest favorite

A bright living area is illuminated by natural light through large windows. A decorative black wall with a welcome message adds character. A comfortable seating arrangement and dining space is featured. Art pieces are displayed, enhancing the creative ambiance of the space.

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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.

4.98 out of 5 average rating, 125 reviews

Guest favorite

A two-story house with a wooden exterior blends into the landscaped surroundings. An expansive front yard features manicured green grass and shrubs. A porch wraps around the upper level, complemented by bicycles stored underneath, while large windows provide views of the outdoor scenery.

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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

5.0 out of 5 average rating, 19 reviews

Superhost

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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!

5.0 out of 5 average rating, 3 reviews

Top guest favorite

The exterior of a contemporary home is presented, featuring a well-maintained lawn with a fire pit surrounded by several outdoor chairs. A hot tub is visible on the side, set against a backdrop of lush greenery and a clear blue sky.

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Stylish Montauk Village Escape for Any Season

Stylish Montauk retreat with 3 bedrooms, 2 full baths, and 2 half baths. Just minutes from beaches, shops, and restaurants. Soak in the hot tub, gather around the fire pit, or savor breathtaking sunsets from the private deck. Modern interiors, central air, and Wi-Fi make it cozy year-round. Spacious, elegant, and inviting, perfect for families, friends, or romantic escapes seeking comfort, luxury, and ultimate Montauk getaway!

5.0 out of 5 average rating, 57 reviews

Guest favorite

An outdoor dining area is located beneath a wooden pergola, surrounded by a spacious lawn. A stone patio features a table with blue metal chairs. Lush greenery is visible in the background, along with a cottage painted in muted colors, accented by vibrant flowering bushes.

Cottage in Montauk

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.

4.87 out of 5 average rating, 126 reviews

Top guest favorite

A bright kitchenette features modern cabinetry and a stainless-steel sink. Adjacent, a dining area with two chairs faces a spacious living room, highlighted by large windows allowing natural light and showcasing a comfortable sofa and wall-mounted TV.

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Dockside 2BR - Marina - Dining - Charter Access Un

Any closer to the marina and you’d be swimming in the Atlantic. Our sweet little cottage sits right on Westlake Marina. From your front door, you can book a charter, grab a bowl of Westlake Fish House’s famous clam chowder, or walk to Gosman’s for a sundae and a sunset. Inside enjoy heated floors, plush beds, and a fully-equipped kitchen, making this a perfect place to land after all the Montauk fun.

4.97 out of 5 average rating, 38 reviews

Top guest favorite

The traditional salt box home is set against a backdrop of Lake Montauk. Features include a spacious upper balcony patio with seating and a lower ground-level patio with loungers and a fire pit. The surrounding yard offers open green space with trees and nearby road access.

Home in Montauk

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".

5.0 out of 5 average rating, 24 reviews