Apartment vacation rentals in Montauk

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Top-rated apartment rentals in Montauk

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Guest favorite

Apartment in Sag Harbor

4.94 out of 5 average rating, 136 reviews

Whaling Captain Pierson's Cottage

Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 515 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Guest favorite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Guest favorite

Apartment in Guilford

4.98 out of 5 average rating, 253 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Guest favorite

Apartment in Hampton Bays

4.96 out of 5 average rating, 268 reviews

The House of the Mermaid aka La Casa della Sirena

Welcome to The House of the Mermaid! Come stay in this newly renovated and decorated basement apartment in my house in a quiet and residential area of Hampton Bays. Close to all that you could ever want; restaurants, bars, shopping, and beaches. Perfect getaway for any season. The Hamptons are known for their amazing Summers at the beach, but don't forget about all that Long Island has to offer throughout the seasons. Shopping at Tanger Outlets, apple/pumpkin picking, and the N.F. vineyards!

Guest favorite

Apartment in Sag Harbor

4.99 out of 5 average rating, 134 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Guest favorite

Apartment in Hampton Bays

4.97 out of 5 average rating, 340 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

Guest favorite

Apartment in New London

4.98 out of 5 average rating, 290 reviews

Quiet Neighborhood home close to everything

Spacious & charming 2 bed RM APT on the 3rd fl of my home, gives you all the comforts of home while you’re away. We are a quick walk to L&M (Yale) Hospital, Mitchell College, And EB NL Campus. Short drive to the Coast Guard Academy, Conn College, Domion (Millstone) and The US Submarine Base. And if you’re here for fun, we are 1.5 miles to Ocean Beach (borrow our pass for free access) 20 min to Mohegan Sun & 25 to Foxwoods and 15 min to Mystic. Follow us on Insta at 199Thames.

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

Guest favorite

Apartment in Montauk

4.97 out of 5 average rating, 150 reviews

Duffy's On Lake Montauk 3

Recently renovated in soft blues and whites, these sleek units offer a full kitchen, washer/dryer, living area and large deck steps from Lake Montauk. Paddle boards , kayaks and beach chairs offered. All units have Bose players and Roku. The units sit at a 90 degree angle to the lake with partial lake views from the deck. The lake and beachfront are a 1 minute walk from the unit. PRICES INCLUDE SUFFOLK COUNTY SALES AND OCCUPANCY TAX

Guest favorite

Apartment in Sag Harbor

4.88 out of 5 average rating, 134 reviews

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. No pets - owner is allergic. No infants/children.

Guest favorite

Apartment in Montauk

4.91 out of 5 average rating, 201 reviews

Montauk Beach Bungalow West

Inquire about discounts for monthly bookings. 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. -