Vacation rentals in Hither Hills

A serene lakeside scene captures padded Adirondack chairs arranged in a row on grassy terrain, facing the lake. The sunset reflects vibrant pink and orange hues across the water, enhancing the peaceful ambiance of the natural setting.

4.99 out of 5 average rating, 182 reviews

Duffy's on Lake Montauk 2

These newly renovated units are located on Lake Montauk, five minute drive from town and the ocean beaches. The property offers paddle boards, kayaks and beach chairs. There is a BBQ grill, a fire pit to enjoy sunsets and lounge chairs lake front to relax. The unit has a full kitchen, washer/dryer, queen bed, small living area, large screen TV and wifi. The units sit at a 90 degree angle to the lake with partial lake views from the deck. PRICES INCLUDE SUFFOLK COUNTY SALES AND OCCUPANCY TAX

4.96 out of 5 average rating, 467 reviews

Cabin in Montauk

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

4.96 out of 5 average rating, 106 reviews

A surfer is seen riding a wave, showcasing a spray of water as it crashes. Three additional surfers are positioned nearby in the water, all engaged in the activity. The scene is set against a clear blue sky and a tranquil ocean backdrop.

Guest suite in Montauk

Twin Pond Ocean View Studio 3

Semi-private path to one of the best beaches in Montauk. Imagine not having to deal with Ditch parking but beach passes included! Twin Pond is a compound on 2.5 acres on Old Montauk Highway. Studio is one of 7 units—galley kitchen (no cooktop) with 180 degree views (1) Qn Size Bed. Walk to Town & restaurants. Modern chic with flat screen TV and WiFi. Ideal for couples/sm family. Outdoor furniture and a gas grill. Dog fee is $150 per dog. Only small to medium size dogs. No cats or other animals.

5 out of 5 average rating, 54 reviews

Montauk Retreat - Steps from Beach and Town

This 2nd floor two room suite across the street from the beach is steps to shops, restaurants & more! The bedroom and living room are divided by a galley kitchen. Perfect for a cozy spring stay for families or couples! Includes toiletries, beach towels & chairs, a fully stocked kitchen with a Keurig and tea kettle, and board games! Features a queen-sized bed and pull-out sofabed, a large smart TV, fast WiFi, dining table and a terrace overlooking a heated pool (Memorial Day to Columbus Day).

5 out of 5 average rating, 75 reviews

A bright kitchen is highlighted by white cabinetry and modern appliances. A central island with a wooden countertop provides additional workspace. Light streams through multiple windows, while green pendant lights add a touch of color above. The kitchen features potted plants and a cozy rug.

Home in Montauk

3 BR/Pool. Walk to Beach & Town!

Vacation at our charming Good Tauk Beach Cottage, a whimsical & retro-inspired retreat nestled in the heart of Montauk, NY. Boasting stunning lake views, our fully renovated 3BR, 2BA cottage features a playful and colorful design, perfect for families & long-term travelers. With a private backyard oasis featuring a sparkling pool, BBQ, and dining patio, our cottage offers the perfect blend of relaxation + entertainment. Plus, you'll love being centrally located from Montauk's top attractions!

A wooden boardwalk extends towards the water, lined with colorful kayaks resting on the sand. A large ship is anchored in the distance, while the sky is painted with shades of orange and purple from the sunset, reflecting on the serene water.

5 out of 5 average rating, 228 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

A serene view of a sandy beach area with tufts of grass, framed by calm waters under a sky dotted with fluffy clouds. The horizon features a distant jetty, contributing to the tranquil coastal atmosphere.

4.98 out of 5 average rating, 84 reviews

Beautiful modern retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy getaway. The open-plan interior (wood stove, high-end furnishings/linens/appliances) leads to a covered patio & large yard. (firepit, shower, grill). Beautiful touches everywhere, landscaped for privacy & just a few blocks to LI Sound & Harbor. 3 mi to Ditch Plains or Town. See last photo for accurate location. Note: Owner is in a separate private studio with own entrance. Ask about pet or flexible rental period. 4 people max INCL KIDS.

4.99 out of 5 average rating, 94 reviews

A wide sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. The landscape includes a sloping dune area lined with sparse vegetation on one side, contributing to the tranquil coastal scene.

Vacation home in Montauk

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a short , 3 block walk to one of the most beautiful ocean beaches in the Hampton's! This apartment is located in beautiful, wooded quiet neighborhood. It is a short drive into town where you will find restaurants and shops. This apartment has an open concept living space with a fully equipped kitchen with everything you need ,2 cozy bedrooms and one bath with a walk in shower. We supply beach towels, chairs, umbrella and beach wagon.

5 out of 5 average rating, 29 reviews

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

Montauk Village

Remarkable newly built home in Montauk, Winter Sunset View, Walk to Beaches and Restaurants. You will have a stylish experience at one of the most sought after seaside destinations. 3 bedroom, 2 full bathroom and 2 half baths. 9 minute walk to village beaches, restaurants/bars, and shopping In the mood to stay in? Enjoy the hot tub and fire pit. Watch the beautiful Montauk Sunsets "winter is best" from the deck! Central air, internet and wifi

An expansive view of the ocean is visible through sliding glass doors. Sunlight illuminates the beach and blue waters, while white curtains gently frame the scene. Outdoor seating, including two white chairs and a chaise lounge, is positioned on the private terrace, inviting relaxation.

4.86 out of 5 average rating, 111 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

A well-maintained outdoor space features a round wooden table with a large red umbrella, surrounded by wooden chairs. Lush greenery and ornamental grasses frame the area, and a scenic view of the ocean is visible in the background, providing a serene setting for outdoor dining.

4.9 out of 5 average rating, 220 reviews

Montauk Beach Bungalow West

Charming, clean, private, quiet, 2 bed one bath ocean view apartment 500 feet from door to ocean beach through lovely dunes. Dine inside or out with view of the moon rising over the breaking waves. Includes BBQ and fire pit. Full kitchen with stove, oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc. - small bathroom and shower and large outdoor shower

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Hither Hills vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Hither Hills

4.92 out of 5 average rating, 172 reviews

The image captures a serene sunset over the water, with vibrant orange and pink hues blending into the sky. In the foreground, two dark umbrellas are positioned over a wooden deck, which features a few tables and chairs. Gentle waves can be seen in the distance.

Resort in Montauk

Montauk Waterfront Loft Room

CarolynRating, 5 stars3 days ago

Great space! Clean and beautifully decorated. Great neighborhood and stunning views of the water. The pool and area were very well taken care of. Clear and simple instructions. We would stay here again and recommend you book this place!

A waterfront sun-deck features several white Adirondack chairs arranged around a stone fire pit. The area is surrounded by a pebbled surface, offering views of the tranquil water. Nearby, additional seating areas are visible along the deck, with the sky displaying clear blue hues.

5 out of 5 average rating, 25 reviews

Sun N Sound Resort, Montauk, NY

RonaldRating, 5 stars3 days ago

Absolutely outstanding stay! The host went above and beyond with exceptional customer service, making us feel truly welcome and cared for from start to finish. Would stay again!

4.96 out of 5 average rating, 272 reviews

Comfortable lounge chairs with green cushions are positioned on a stone patio, offering views of a nearby swimming pool. Lush greenery surrounds the area, and sunlight filters through the trees, creating a serene outdoor space that invites relaxation.

Private room in Montauk

The Black and White Room.

AdamRating, 5 stars4 months ago

Host is extremely accommodating and considerate. When it snowed he put salt down. Beautiful place with a beautiful fireplace. Peaceful. Host is responsive to all questions. The best stay we had out east and we will return again.

4.9 out of 5 average rating, 10 reviews

Vacation home in Montauk

Lovely vacation home, steps away from the ocean!

KpRating, 5 stars7 months ago

Excellent location. Enough space for 4 people with standard amenities. Hosts were responsive and accommodating. Would recommend this home.

The outdoor deck features a seating area with four chairs, offering a clear view of the sandy beach and calm waters. Lush greenery is visible in the foreground, leading to the shoreline. A serene blue sky stretches overhead, complementing the tranquil seaside setting.

5 out of 5 average rating, 6 reviews

Condo on the Sound - Navy Beach

AshleyRating, 5 stars7 months ago

Tara’s place was a perfect for a weekend getaway! Close enough to town and great view of the sunset!

5 out of 5 average rating, 8 reviews

A landscaped outdoor area features a gravel surface with two lounge chairs positioned near an outdoor fire pit. Two freestanding umbrellas offer shade, and the surroundings include vibrant greenery and flowering plants. The cottage's exterior is visible, showcasing large black windows.

Home in East Hampton

New Designer Cottage: Steps To Beach On 1.5 Acres

SarahRating, 5 stars9 months ago

I had the absolute joy of staying at Katie and Robs magical home for a long weekend celebrating my mothers 75th birthday with my sister. What they have created is a true sanctuary! We all felt like we were on retreat. Every detail of their home is thoughtfully done and is just stunning! The bedding was luxurious, and it felt like you were in a home out of a design magazine. It was also in the the most beautiful setting, with an easy walk to a stunning bay, and a short drive to shopping and restaurants. It was truly dreamy!

The exterior of a distinctive resort is displayed, showcasing a blend of architectural styles with red brick and timber accents. A well-maintained lawn surrounds the buildings, and a clear blue sky is visible above, enhancing the inviting atmosphere of the property.