Holiday houses in Sagaponack

4.94 out of 5 average rating, 154 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".)

4.96 out of 5 average rating, 156 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.

4.76 out of 5 average rating, 41 reviews

Home in The Hamptons

Cheerful 3 bed-3bath beach cottage home with pool

Heart of the Hamptons is situated this bright, beach house 5 minutes from the ocean, BH/Sag Harbor town, & Wolfer vineyards. 2 master suites w/ ensuite bathrooms and an additional guest room with adjacent bathroom that comfortably sleeps 6 -1 King, 1 queen, 2 twin. Open kitchen that adjoins the dining area and the double height living room w/ fireplace. Sparkling heated pool (OPEN MD-mid Sept) and palatial lawns with room to roam. Keep it simple at this peaceful and centrally located getaway.

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Guest suite in The Hamptons

4.79 out of 5 average rating, 189 reviews

Serenity Near the Beach

Perfectly situated near beaches, waterfront dining , town, and art sites. Peaceful private room and full bathroom with private entrance from outside. Equipped with everything you need to enjoy beach. Enjoy beautiful view of natural setting from deck. We provide microwave, coffee maker, mini refrigerator, dishware, and table in room and outdoors - does not include living room or kitchen. Perfect for work or vacation. Space attached to the house but 100% private. No smoking. No children.

4.98 out of 5 average rating, 176 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!

4.95 out of 5 average rating, 80 reviews

Cottage in The Hamptons

Steps to the Beach - Designer Cove House Cottage

All new modern interior and exterior furnishings by luxury interior designer. Enjoy fabulous water views on the expansive mahogany deck from this sweet beach cottage that was completely renovated and is a short walk to beautiful Long Beach and just a couple of miles to Sag Harbor's Main St. The home features an open floor plan, cozy gas fireplace, an updated kitchen with stainless appliances and Viking range. Three bedrooms (one with a private office) and an outdoor shower.

4.93 out of 5 average rating, 121 reviews

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 .

Guest suite in The Hamptons

4.96 out of 5 average rating, 165 reviews

B our guest! Central 2 all Prvt entrance Prvt Pool

Beautiful, bright, spacious King suite w fireplace, two 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/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/snacks and breakfast treats provided.

Guest suite in The Hamptons

4.9 out of 5 average rating, 356 reviews

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. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

4.96 out of 5 average rating, 28 reviews

Villa in The Hamptons

SERENITY AT SHOREWOOD Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

4.98 out of 5 average rating, 324 reviews

Cottage in The Hamptons

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

5 out of 5 average rating, 17 reviews

Home in The Hamptons

Sag Harbor Village Waterfront

Peaceful, waterfront cottage on Upper Sag Harbor Cove, located within Sag Harbor Village. There is a dock with room for a medium size boat or jet skis. House includes three stand up paddle boards, two kayaks, two bicycles an outdoor grill and outdoor dining area and seating.

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Other great holiday rentals in Sagaponack

5 out of 5 average rating, 121 reviews

Light, bright and airy getaway!

CatherineRating, 5 stars10 months ago

Denyse’s apartment cottage was perfect for my stay. I wish i was there longer than one short night! Everything was spotless. Denyse met me when i arrived to show me around. All around excellent and i highly recommend her place when in the area.

4.96 out of 5 average rating, 216 reviews

Sag Harbor Home, Perfect for the Solo Traveler

MarcosRating, 5 stars2 weeks ago

Staying at Barbara’s was, without question, the best Airbnb experience I’ve ever had — and I’ve had some truly wonderful ones. From the moment I arrived, she greeted me with the warmest smile and a peaceful, welcoming energy that immediately made me feel at home. She had fresh cookies waiting for me, bottled water by the bedside, and made sure I had everything I needed to feel comfortable and cared for. In the morning, I woke up to the smell of fresh coffee and the most beautiful breakfast spread — homemade zucchini bread, muffins, fruit, teas, and English muffins — all lovingly prepared. Her home is immaculate, beautifully decorated, and so thoughtfully arranged. I had one of the most restful nights of sleep I can remember in her incredibly comfy bed, waking up completely recharged. And her cat? The cutest I’ve ever seen — gentle, friendly, and just added to the charm of the whole experience. Barbara is a truly exceptional host in every way. I left her home feeling so grateful, res

Home in The Hamptons

4.89 out of 5 average rating, 54 reviews

A blissful place in Bridgehampton

ViliaRating, 5 stars10 months ago

I had a wonderful stay in July. The house is well-located between Bridgehampton and Sag Harbor. it is very clean and furnished nicely. The back yard and pool are sheltered and beautiful. The owners were very helpful and responsive.

4.95 out of 5 average rating, 39 reviews

Cottage in The Hamptons

*Chic, Family Friendly Hamptons Cottage With Pool

BrianRating, 5 stars5 months ago

This is an amazing location. Beautiful kitchen with all of the amenities. The living area is comfortable and spacious. The whole home feels much larger than it appears in the photos. Would 100% stay here again.

5 out of 5 average rating, 8 reviews

Southampton apt walk to village

RoshniRating, 5 stars1 week ago

Had a lovely stay! Beautiful apartment with private entrance. The living spaces, bathroom, kitchen and bedroom were modern, very clean and had all the necessary amenities for a comfortable stay. The place is within walking distance of the train station and village. Would absolutely stay here again.

4.96 out of 5 average rating, 153 reviews

Perfect in SH ~ Private Room Near Village Center

NeeleRating, 5 stars1 month ago

we had such a lovely time at Jayne’s place! The room was very clean, we loved the garden and her cats! It was perfect for a little city getaway! We definitely want to come back:)

4.95 out of 5 average rating, 164 reviews

Lily Pad ~In the Prettiest Cottage on Lily Pond

RuthRating, 5 stars1 week ago

My wife and I really enjoyed our stay. Joelle was really friendly, cheerful and vibrant. We really enjoyed meeting her and chatting. While we saw her every day she also gave us our own space and pretty much free-run of the living-room and kitchen area. Her home is lovely and true to the pictures. The view of the lily pond at the back is beautiful. The location is great, just a few minutes drive from Sag Harbor. As other reviewers have noted, there was some road-noise coming through to the bedroom at night. However, this was easily overcome by turning the fan on. We would happily stay again. thank you Joelle!

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