Holiday rentals in Sagaponack

4.93 out of 5 average rating, 151 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

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 Bridgehampton

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.

4.98 out of 5 average rating, 178 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 Sag Harbor

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.

Guest suite in East Hampton

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 Sag Harbor

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, 293 reviews

Home in Sag Harbor

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

4.98 out of 5 average rating, 325 reviews

Cottage in East Hampton

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 Sag Harbor

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

Home in East Hampton

5 out of 5 average rating, 24 reviews

Walk to village and hidden from the hustle EH home

Sneha SusanRating, 5 stars14 months ago

Victors place was warm and cozy - the perfect retreat from the hustle and bustle of everyday life. It was private and made us feel right at home. Victors house is well stocked with all the required supplies. They have the Monopoly - Hampton edition which made it fun while driving around the Hamptons.

Private room in Sag Harbor

4.96 out of 5 average rating, 216 reviews

Sag Harbor Home, Perfect for the Solo Traveler

MarcosRating, 5 stars3 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

5 out of 5 average rating, 10 reviews

Home in Water Mill

Waterfront home next to the beach in Southampton !

ManuelaRating, 5 stars3 weeks ago

Our family of five just spent Memorial Day weekend at this house. The views and location are amazing. Rohit is very responsive and friendly. The house is very practical, super clean, very nice kitchen, everything is new. Hope to go back soon!

Home in Bridgehampton

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 Bridgehampton

*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, 21 reviews

Cozy Get Away Sag Harbor Village Studio

DouglasRating, 5 stars1 day ago

Despite the elevated prices in Sag Harbor this weekend, likely due to the long Juneteenth holiday, the rate, while high, was well worth it compared to other available options. The property offered a perfect balance of peaceful and private, yet still conveniently close to the heart of town. I would absolutely stay here again and highly recommend it to anyone looking for a relaxing escape that’s still within easy reach of the action.

Private room in Southampton

4.96 out of 5 average rating, 154 reviews

Perfect in SH ~ Private Room Near Village Center

StephenRating, 5 stars2 weeks ago

Jayne’s home is a beautiful retreat. The bedrooms are lovely, the setting is beautiful and she takes pride in her gardens and caring for her guests. She is a great host. This was our second stay with her and she always has repeat visits from guests. Thank you so much!