14 Best Montauk Beach House Rentals, Cottages, & Surf Shacks

As the pandemic continues toward the one-year mark, Americans across the country are searching for safe ways to get away and escape the day-to-day. For 8.5 million New Yorkers and other Tri-State residents looking beyond the Catksills & Hudson Valley, the sleepy beach town of Montauk offers beautiful beaches, ample art galleries, and some of the region's best surf (and horseback riding?!). Not to mention a wealth of cute cottage and contemporary cabins straight out of a Wes Anderson film. All just over two-and-a-half hours from Manhattan.

Located on the east end of the South Fork peninsula of Long Island, Montauk exists just beyond the glitz and the glamour of the highly-frequented Hamptons and laid-back bayside town of Sag Harbor. But it’s so much more than just a summer getaway. The hamlet of just over 3,600 residents offers its visitors a great deal, including six state parks, recreational and commercial fishing, and of course, beautiful beaches.

Over the decade, the secluded nature of Montauk has earned it a well-known locale for notable residents, many of whom utilized the town to influence their art. In the 1970's Andy Warhol owned one of the more notorious estates-recently listed for sale at $65 million-known for hosting guests including Mick Jagger, Jackie Onassis, and John Lennon. Photographer Peter Beard—prior to his disappearance last spring—contrasted his world-renowned images of Kenya's wilderness and national parks with his six acres basecamp estate overlooking the Atlantic Ocean (which be also bought in 1972 for $135,000). And years later, the foundation of playwright Edward Albee funded the William Flanagan Memorial Creative Persons Center as a residence for writers and visual artists.

More recently, Montauk has seen its influence reflected in more popular culture, from music to literature to television. Perhaps most notably, however, is its use as a plot-point of Charlie Kaufman’s 2004 film “Eternal Sunshine of the Spotless Mind.” Countless surf books and architectural hardcovers include the area at land's end, as well.

If you’re interested in garnering some of the genius artistic energy, looking for a public beach worth splaying out on, or keen to learn to surf, we at Field Mag have found a slew of delightful Montauk rentals to visit and enjoy, regardless of season. Montauk is modestly-sized as well so park the rental car at your cottage and spend the rest of your visit on foot. Each one of the following 14 Airbnb beach houses, VRBO bungalows, and rental cabins offers a change to your WFH routine or a true holiday away from your cramped apartment, and could inspire your creative work even further.

Montauk, NY — Waterfront Cottage

Vibe: Home Sweet Home

This two-bedroom cottage provides a delightful Montauk getaway with access to a pond, alongside a fire pit, paddle boards, and kayaks for the good weather. Originally erected by a French-Canadian fisherman in the 1930s, the cottage is one of two properties on this compound for visitors to make full use of their European-style adventure right along the waters of New York. The home decor is a mix of tchotchkes from international adventures and homemade treasures from Montauk craftspeople, providing all the more charm to this home away from home.

Rate: $319/night

Montauk, NY — Tiny Cottage

Vibe: Simple and Sweet

A cozy vacation rental right off Gurney’s Beach Resort and adjacent to Hither Hill — the only luxury Hamptons hotel located right on the beach — and a public bike path, this recently-opened cottage gives a great deal of privacy while also providing tranquility. On top of sharing this tiny space (measuring just 12 feet by 16 feet) with a furry friend or a partner, host Jason recommends taking advantage of a large spacious mahogany outdoor shower and a clay Chiminea fireplace on the outdoor deck. Of course, perhaps a bit more doable when it’s warmer — but that doesn’t diminish the fact that this find is perfect for those seeking a relaxed adventure.

Rate: $222/night

Montauk, NY — Bright & Modern A

Vibe: Modern Muse

For travelers seeking a bit more space to stretch their legs, this 3-bedroom A-Frame esque vacation home is great for each and every season of the year. With 16-foot high ceilings and tons of natural light, the space offers its visitors loads of open space to relax, entertain, and enjoy, including outdoor dining for 8-10, six brand new bicycles for exploration, and a built-in hot tub, open year round. Additionally, the home is surrounded by a large nature preserve, helping to make it feel like a true hidden gem.

Rate: $462/night

Montauk, NY — Idyllic Cottage

Vibe: Home on the Harbor

Renovated in 2016, this idyllic space calls to mind the picture-perfect space for travelers to enjoy the Hamptons to the utmost. At 1,200 square feet, the home offers tons of space for its visitors, alongside beautiful views off the Accabonic Harbor. Guests can enjoy some outdoor time on the large deck, or view the nesting family of Bald Eagles from the warmth of the indoor, open-concept living area.

Rate: $495/night

Montauk, NY — Look Sharp A-Frame

Vibe: Easy, Breezy, Beautiful - Beach House.

A few degrees shy of a gable or A-Frame house, this abode just yells ‘beach’! The bright, all-white interior is simple but clean and cozy, with the warm brick fireplace taking center stage. A walk to Ditch Plains beach, spend the day surfing then come home and chill on the deck, sans sand. Be warned though, this one comes with a 14 night minimum stay, and a hefty price tag. "That's New York, baby!"

Rate: $1,072/night

Montauk, NY — Classic 40's Cottage

Vibe: Wood Panel Glory

Harkening back to architectural charms of 1945, this remodeled two-story cottage offers visitors both old-school charm and newfound amenities. Upon entering, you can lounge in the enclosed front porch and dining area, or head straight upstairs toward the “tree-house” style bedroom, featuring a Juliet balcony. On top of its charms, the home also offers guests private access to the beach right off the Atlantic Ocean.

Rate: $665/night

Montauk, NY — Secluded Beachfront Cabin

Vibe: Contemporary Surf Shack

This find is quite possibly the largest home we can recommend to Field Mag readers — but it additionally adds so many vintage aspects. Guests can thoroughly enjoy and relax in all of the aspects of this classic A-Frame, with its four bedrooms, open concept kitchen, and living room all facing the private beach on Lake Montauk. Owner Brandon Holly recommends utilizing the stone fireplace to ward off the chilly weather and take in the lake’s gorgeous views at sunrise and sunset or taking the provided beach bikes down the road to Gin Beach.

Rate: $600/night

Montauk, NY — Twin Pond Oceanview Cottage

Vibe: Beachside Bliss

Harkening back to long ago adventures, this cottage is a renovated part of the vintage motel Twin Pond, all along the Old Montauk Highway. Six guests can enjoy the semi-private property with its open-concept living room with 180-degree views of the Atlantic, and grab your beach towel to head down to the gorgeous pristine beaches throughout the hamlet.

Rate: $750/night

Montauk, NY — Contemporary Architect's Cabin

Vibe: The Belly of the Whale

This newly-built contemporary cottage along Three Mile Harbor provides guests a stylish stay at the hands of a determined architect. Designed with an open-concept feel, the home is meant to be lived in — and the owner encourages guests to walk around the home and the property barefoot to become one with the space. Additionally, the unique home offers 15-foot-tall ceilings which allow great sunlight throughout the day, a large open air porch, a spacious private yard and boat rental. For some exercise, head to the East Hampton tennis court for the day.

Rate: $414/night

Montauk, NY — 4 Season Beach House

Vibe: Brooklyn Loft meets Beach House

This cabin was reimagined to reflect the feel of a Brooklyn loft with all of the joys of a cozy hideaway. The owners consider both fall and winter to be marvelous times to make use of this home, with amenities including a crackling fireplace and cedar lined sauna set up to enjoy the most of the indoors while it’s chilly outside. A blend of retro and new styling, the home mixes the benefits of European minimalist style with a beach house, all awaiting your visit to escape the city

Rate: $900/night

Montauk, NY — Oceanview Studio

Vibe: Studio Sweet Studio

In the winter, a small joy is sitting in front of crackling fire — with this property, you have the opportunity to lounge, warm up, and enjoy (and, dare we say, make some s’mores?). This cottage is cozy and quaint for just two guests, with a full queen size bed, full kitchen, and a mod, mid century fireplace. In pleasant weather, the hosts recommend guests to fully utilize the chairs and grill right outdoors, before heading down to South Edison Beach along a short-walk through the dunes or head inland to Hither Hills State Park.

Rate: $195/night

Montauk, NY — Spacious Retreat

Vibe: Family-Friendly

A large compound for up to eight guests, this spacious bungalow offers visitors a peaceful space close enough to the buzz of Montauk’s main downtown. An airy and sunny home, the space offers up many beautiful aspects for warm weather: a sunroom, a pergola, a pond, a firepit, a large BBQ grill and an outdoor eating area complete with lounge chairs. For colder weather, guests can make great use of the indoor steam shower and wide open living space to enjoy family activities.

Rate: $486/night

Montauk, NY — Laid-Back Bungalow

Vibe: California Surf Shack Meets Brooklyn Makerspace

A quaint getaway but with a 2021 spin. Recently renovated and designed, this two-bedroom bungalow brings the elements of modern luxuries (open concept spaces, bright paint colors, and eclectic furniture) with the relaxing and sophisticated parts of an old-school fisherman’s cottage. With views of Fort Pond, The home has an abundance of natural light, making for perfect calming indoors time, while also offering a fully fenced-in yard with space for tanning, barbecuing, and general merriment. The Fort Pond Bay beach, ocean beach, and Downtown Montauk are all within walking distance if you’re looking for things to do.

Rate: $400/night

Montauk, NY — Renovated Bungalow

Vibe: Rustic Contemporary

This newly renovated space is incredibly close to many of Montauk’s delightful attractions, including Gosman's, Salivars Restaurant, and a number of secluded beaches. On the property itself, guests can enjoy the outdoor space with family and friends, with a gorgeous hammock, delightful flower garden, and BBQ pits. Indoors, the soft wood accents throughout the home pair with the quaint tranquility of fully enjoying a WFH visit away from your home.

Rate: $450/night