Holiday rentals in Northwest Harbor

Chic, 1 block to waterfront dining,8 mins Main St

Make yourself at home at this chic serene Hamptons oasis! Located just 1 block to waterfront dining + 8 mins to Main St Enjoy your large private home nestled in nature w/ zen vibes. Hang poolside, spark up the firepit + BBQ, enjoy the outdoor shower, cook in your Chef's kitchen + stream on your 80' TV. Walk 1 block to waterfront dining + cafe to enjoy morning coffee on the sea + dinner + cocktails while watching the sun set over the harbor. You'll be 8 mins to Main St., beaches + so much more!

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".)

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Luxe Beach Cottage-Steps to Water-USGolf-Firepit

Kick back and relax in this calm, stylish beach cottage with NEW Kitchen and NEW bathroom (completed April 2026) in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, BBQ and my own tiny cottage “Bouy Cottage” is across the lawn so I (or other guests may be there in May-Sept. Beach chairs, umbrella and smiles!

Barefoot Bliss | Quiet Family Retreat Heated Pool

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

Chic house NW Woods. Massive 50 ft heated pool.

Kick back and relax in this calm, stylish space. Just 10 minutes from beautiful sammy's beach,this home is perfectly situated for enjoying the Natural beauty of East Hampton. Grab the Provided beach chairs and towels for a relaxing day by the water. Guests consistently rave about the stunning 50-foot heated pool,beautifully landscaped grounds,and thoughtfully curated decor that creates that perfect East hampton getaway. 10 minutes to the Heart of Town. Fast Responsive Communication.

Peaceful cottage

Take a break and unwind at this quiet, peaceful retreat! This 3 level cottage includes lower level garage parking for one car and laundry. The main level holds a full kitchen, spacious living room, and half bath. The second floor bedroom has an en-suite bathroom. Situated beside the main house, on 2.5 acres surrounded by forest, with easy access to trails. Close to ocean and bay beaches, midway between East Hampton and Sag Harbor. Perfect for a couple with an appreciation for nature!

4 BR/3BA Quiet Pool Home

We welcome you to our family home, up to 5 guests, pets are welcome with additional pet fee. Nice new pool and surrounding deck with outdoor sitting area, chairs, umbrella, and charcoal grill. 1 gbps internet for movies streaming on disney plus, prime video, or for your work. 5-8 minutes to town and the beaches. Plenty of nice restaurants and great local shopping. We don't allow other guests on property that is not mentioned in advance. No gatherings and no parties. Thank You.

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Beachglass Barn en-suite retreat prvt pool 2 baths

Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.