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Holiday rentals in Ditch Plains

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Top-rated holiday rentals in Ditch Plains

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The interior of the cabin features a spacious bed framed by large windows that invite natural light. A small dining table is set beside a plant, and the wooden ceiling enhances the cozy ambiance. A decorative blanket adds a splash of color to the bed.
Cabin in Montauk
4.96 out of 5 average rating, 498 reviews

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Guest favourite
A cozy bedroom features a queen-sized bed covered with a red blanket. Surrounded by wooden walls, large windows allow natural light to illuminate the space. A vibrant area rug sits on the floor, while decorative surfboards and a wooden dresser add character to the room.
Cottage in Montauk
4.95 out of 5 average rating, 76 reviews

Huge Cottage W Private Bath, indoor&outdoor Shower

Your very own Montauk Cottage on green acres. 1 mile to Ditch, half mile to L.I. Sound **2 NIGHT MIN Very Private Only a single, queen-sized bed. ALL friendly DOGS welcome provided they are always leashed, do not tear up furnishings, bark when left alone, are picked up after outside and are kept off the furniture. NO UN-HOUSEBROKEN PUPPIES OR WEE WEE PAD DOGS PLEASE. WE ACCEPT DOGS ONLY. NO CATS OR OTHER PETS. NO EXCEPTIONS. Friendly dogs & Chickens on property. Roosters will Crow in the AM.

Top guest favourite
An outdoor seating area features a round table surrounded by four wooden chairs under a vibrant red umbrella. The grassy ground extends towards a clear view of the ocean, framed by trees and shrubs, with a gravel path leading away from the space.
Bungalow in Montauk
4.93 out of 5 average rating, 108 reviews

Montauk Beach Bungalow East Apt.

Charming, clean, private, quiet, 2 bed 1 bath ocean view apartment across from ocean beach via through dunes path. Check the surf from the living room window. Dine in or out with the moon rising over the ocean. Includes BBQ and fire pit, outside table. Private entrance, lawn, outdoor shower, storage space for bikes, etc. Perfect vacation rental. Full kitchen with stove oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc - monthly discounts. Small bathrm & shower

Top guest favourite
An open living area features a comfortable sectional sofa and a large area rug, with natural light streaming through multiple windows. A dining table is visible, accompanied by stools, and the kitchen area includes modern appliances and a view into the outdoor patio space.
Flat in Montauk
4.95 out of 5 average rating, 130 reviews

Modern Montauk retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy, all-season getaway with open-plan interior & large, private fenced yard. • 950 sq ft, 2 BRs (compact but comfy), 1 Ba, full high-end kitchen, W/D, A/C • Wood stove, Solo stove, patio, outdoor shower, high-end linens & furnishings/decor • Steps to LI Sound & Harbor. 3 mi to ocean/Town • Owner is in a private studio w/ own entrance in the house. No shared spaces! • Ask about dogs & flexible rental periods CLICK MORE for IMPORTANT INFO!

Guest favourite
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.
Home in Montauk
5 out of 5 average rating, 13 reviews

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

Top guest favourite
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.
Home in Montauk
4.98 out of 5 average rating, 118 reviews

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.

Top guest favourite
The entrance features a glass door that opens to a welcoming living space. Two lanterns flank the doorway, providing soft illumination, while a cozy armchair is visible inside. Pebbled pathways lead towards the entrance, setting a relaxing tone for arrivals.
Flat in Montauk
5 out of 5 average rating, 23 reviews

Guest Suite in Montauk

Forget your worries, and relax in this newly renovated ground floor, studio apartment. Your private entrance opens to an expansive living space, welcoming you to your Montauk get away! Queen bed. L-shaped couch (with capacity for one-additional guest. Kitchenette with seating welcomes you to eat at home. In addition to the private bathroom, there is access to a shared outdoor shower. Baby/toddler supplies available upon request. Two night minimum stay.

Top guest favourite
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.
Home in Montauk
5 out of 5 average rating, 55 reviews

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!

Guest favourite
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
4.88 out of 5 average rating, 121 reviews

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.

Top guest favourite
A bright kitchen features a large island with wooden countertop and seating for three. Stainless steel appliances and open shelving provide ample storage, while large windows allow natural light to fill the space. French doors open to a deck area with views of the outdoors.
Home in Montauk
4.99 out of 5 average rating, 80 reviews

Renovated Montauk Home

This 3 bedroom, 2.5 bath home is located close to all that Montauk has to offer. Main level offers the master bedroom with on suite bath, open living kitchen & dining area with French doors off of the kitchen leading to the back deck. Second level has 2 additional guest bedrooms and full bathroom. Additional features include outdoor shower, washer and dryer, BBQ grill, WiFi and TV. RR#26-158

Guest favourite
A bright living area features a spacious sectional sofa adorned with blue pillows, positioned near large windows that offer panoramic views of the water. A rustic coffee table adds a touch of charm, while the light-colored walls create a serene ambiance.
Cottage in Montauk
4.88 out of 5 average rating, 252 reviews

Waterfront Cottage, Fort Pond MTK

Perfect cottage perched above Fort Pond with epic views and relaxed bohemian vibes. The cottage is private with a private deck on shared grounds with a fire pit, hammocks, paddle boards, kayak, and lake access. The grounds are expertly landscaped and take full advantage of fort pond views. We do live on the property full time and enjoy making our space a safe and clean environment.

Guest favourite
The exterior of the beach house is presented, showcasing a dark blue façade complemented by a wooden deck. A white door is visible, flanked by two large windows that allow natural light. Surrounding greenery adds to the inviting entrance.
Home in Montauk
4.9 out of 5 average rating, 501 reviews

DITCH PLAINS SURF HOUSE

Beach house on quiet street, 200 yards to Montauk's best surfing beach, Ditch Plains. The house is a simple all white home with 2 decks, BBQ, bikes, kayak, and easy open floorplan. You can hear the ocean all day long on this hidden Montauk street. Easily walk or bike to the beach, where you find waves, food trucks in the summer & miles of sand and ocean heading west to Montauk.

Popular amenities for Ditch Plains holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Montauk
  6. Ditch Plains