Montauk has long been known as a summer weekend getaway for New Yorkers who want to avoid the much-glamorized (and pricier) Hamptons. Located on the far, eastern end of Long Island, Montauk has long been lauded as “the anti-Hamptons” and endearingly referred to as “the end of the world.”
However, Montauk’s charm extends well beyond the summer and into the fall and winter months, as there is still plenty to do in the offseason that gives visitors a taste of this little gem less than 150 miles from NYC—and the best way to stay is by renting one of the many cute cottages along the beach available all year round.
A Beachy Retreat With Picturesque Views
Located in the lovely Heather Hills area of Montauk, the Hither House Cottages offer the perfect escape for those looking to visit this gorgeous town in the offseason. Each of the Hither House’s Cottages has something special to offer every traveler, whether they are looking for a fun, busy weekend or a peaceful, relaxing getaway just minutes from the Atlantic Ocean.
- Address: 10 Lincoln Rd. Montauk NY
- Hours: Monday-Sunday 9:00 AM-12:00 AM
- Contact: (631) 668-2714 or (631) 709-2012
Hither House Cottages has a variety of accommodations, each with its own distinctive flair and décor. The rates provided below only reflect off-season (Nov.1-March 31) and after-season (Sept.10-Nov. 1) nightly and weekly rates, are based on 2 person occupancy and do not include tax and service fees. Rates are subject to change, so be sure to check their website for the most current info.
Cozy wood paneling complements comfy, airy rooms in this popular cottage that sleeps up to 4 people. There's also a patio area where guests can relax and have a BBQ or get together.
- Off-Season: Weekdays $285 and up, Weekends $325 and up, Weekly $2,155 and up
- After Season: Weekdays $365 and up, Weekends $395 and up, Weekly $2,645 and up
This one-bedroom studio is bright and cozy, with a wood stove and seating area for relaxing, hanging out, or just soaking in the chill Montauk vibes. There’s also a full kitchen area for whipping up some delicious meals for a romantic night in.
- Off-Season: Weekdays $145 and up, Weekends $155 and up, Weekly $1,045 and up
- After Season: Weekdays $205 and up, Weekends $225 and up, Weekly $1,455 and up
Seaview Cottage and Guest House Suite
An intimate cottage that sleeps two people, the Seaview Cottage boasts a partial ocean view and plenty of windows and comfy furnishings. The Guesthouse Suite is another attractive two-person option; its wood paneling is warm and inviting while its back deck and small yard are perfect for enjoying both the crisp fall and brisk winter air.
- Off-Season: Weekdays $135, Weekends $145, Weekly $975
- After Season: Weekdays $185, Weekends $205, Weekly $1,355
This one-bedroom cottage is a cozy couple’s retreat with rustic wood paneling and vibrant, blue kitchen cabinetry that has a cool, beachy vibe.
- Off-Season: Weekdays $105, Weekends $155, Weekly $765
- After Season: Weekdays $145, Weekends $155, Weekly $1,045
East And West Cottages
Both the east and west cottages are one-bedroom, offer a partial ocean view, and sleeps two to four people. Complete with a grassy backyard area for relaxing and comfy common areas, these cottages are perfect for a getaway with friends or family.
- Off-Season: Weekdays $145 and up, Weekends $155 and up, Weekly $1,045
- After Season: Weekdays $195 and up, Weekends $235 and up, Weekly $1,485 and up
North And South Cottages
Each of these cottages has a private deck and sleeps up to four people. The spacious outdoor area is great for fall hangouts (winter, too— just bundle up!) and the inside is a homey and welcoming place to relax and get warm at the end of the day.
- Off-Season: Weekdays $130 and up, Weekends $135 and up, Weekly $925 and up
- After Season: Weekdays $185 and up, Weekends $205 and up, Weekly $1,355 and up
Things To Do In Montauk
Though it's known as a summer town, visitors can find also find something special in Montauk in the fall and winter. Whether it’s relaxation and quiet beaches, peace and solitude, and beautiful views in the winter; or fewer crowds and still-warm water, swimming, surfing, and restaurants a-plenty in the fall, Montauk’s got it—complete with a charming small-town vibe and stunning, picturesque views.
Fall Flavor And Flair
In the fall, the water is still warm and many of the restaurants, bars, and shops are still open for those who like a bit of bustle without too much hustle. This is also a great time to hike around Montauk's many trails.
- Have some good eats at fresh restaurants like the Harvest on Fort Pond. A local fave with farm-to-table tasty Italian fare and a family-friendly atmosphere. Seafood lovers will also love Inlet, where they can nosh on Montauk’s famous Pearl Oysters. Clam Bar is another great option for bris, fall outdoor dining, and the good news is, it’s close to Hither Hills!
- Visit the Montauk Brewery for some fun vibes and great-tasting options like the Pumpkin Ale.
- Take a hike or a walk on the beach.
- Visit Camp Hero State Park and see the lighthouse and many other historic buildings.
- Take a fishing charter or boat tour.
- There are plenty of nearby towns like Sag Harbor and Amagansett for a fun afternoon or day trip.
Winter Wonderland That’s Oh So Quiet
Montauk in the winter is quiet—many of the restaurants and shops are closed for the season, so visitors who want a busier atmosphere would be better off visiting in the spring or summer. However, lovers of fantastic views, peace and quiet, and the eerie beauty of a deserted beach will find Montauk to be the perfect winter getaway.
- Take a walk along the beach. Yes, bundling up is almost certainly a must, but the blue ocean and brisk air are well worth a little chill in your bones.
- Have a tasty dinner at Scarpetta’s and enjoy their delish seafood and top-of-the-line wine selection, or head to Shagwong for a burger, beer, and cool pub vibes.
- Get warm in an Igloo at Gurney’s Montauk. These tiny huts are super cute, cozy, and fun—and come in a variety of themes from Harry Potter to Astrology. The best part is, the proceeds go to charity.
- Have a spa day.
- Visit nearby towns like Bridgehampton and East Hampton for more shopping, entertainment, and restaurant options.
- Relax with hot chocolate in the warmth of your cottage.
Sure, Montauk is super fun in the summer—but for travelers who enjoy a quieter vacation that still offers plenty to see and do, winter and fall flings are where it’s at. Start planning your off- or after-season getaway today and imagine your future self sitting on a quiet, serene beach or cozying up in a comfy cottage—all in the charming town of Montauk.