Holiday rentals in Bridgehampton

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.

5 out of 5 average rating, 9 reviews

Home in Sag Harbor

Oh Buoy! Charming Cottage Steps to Beach | Firepit

This nautical-inspired "tiny house" cottage in beloved Sag Harbor is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. The sunny living room features a sitting area and stylish kitchenette. The bedroom has a full sized-bed and en suite bath. Fully appointed for your stay, just bring your bathing suit! Outside is your own little deck with a bistro table and a fire pit / BBQ area, and my own house is just across the lawn so I'm readily accessible! 1 parking spot.

Superhost

Apartment in Bridgehampton

4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Beautiful duplex corner townhouse unit completely renovated in 2021 & in the heart of Bridgehampton Village. 2 min walk to shops, restaurants, main street and a bicycle ride to the beach. Situated all the way at the end of the building it provides ample privacy with Pool open July 4 - Labor Day only. Free parking (2 spots) w/ extra guest parking. Central air conditioning, private patio, ring doorbell/cam, self check in, curated kitchen w/ all supplies. Linens, towels, soap & shamp included

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!

4.85 out of 5 average rating, 34 reviews

Home in Sag Harbor

Curated Artist Home with New Pool

Light, bright, and conveniently located, the “10 minute house" is 10 min to Sag Harbor Main Street, Southampton Main, and Watermill. 5 minutes to Long Beach and 5 seconds to a brand new gunite swimming pool. Next to Elizabeth Morton wildlife preserve with hiking, birding, and beach. Noyack Deli, Bell & Anchor, and Cromers Market nearby. Gigabit internet, heat / AC, high end fixtures and furniture. Substantial artwork. Sustainability focused home. Pets allowed with additional fee.

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.

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 .

4.99 out of 5 average rating, 70 reviews

Cottage in Sag Harbor

Charming Scandinavian Inspired Beach Cottage

Steps from Circle Beach. Charming 2 bed/ 2.5 bath w a separate studio w a twin daybed and 1/2 bath, outdoor shower, large outdoor entertaining patio with a grill. The master bed has a queen bed and the bunk room has a full bed w a twin on bed on top. Located in the cute beach community of Pine Neck, this is Sag Harbor's best kept secret! Chef's kitchen is equipped with top of the line appliances and gadgets. The master bathroom features a clawfoot soaking tub.

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.

Guest house in Sag Harbor

4.86 out of 5 average rating, 107 reviews

Charming 2BR Cottage, Walk to Town

Beech Tree Cottage is a charming 2-bedroom, 1-bath cottage conveniently located in the peaceful historic district of Sag Harbor, NY. It is a 5-minute walk along the waterfront to Main Street and the center of the village. PLEASE NOTE: We have a 2 night MINIMUM stay for bookings and 3 nights on holiday weekends. Please review our cancellation policy and house rules before making a request.

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.

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Popular amenities for Bridgehampton holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Bridgehampton

Home in Bridgehampton

5 out of 5 average rating, 4 reviews

Hamptons oasis with private yard and salt pool

KatieRating, 5 stars11 months ago

We had a great time at Casa Birchwood in Bridgehampton! Carl was a very responsive and proactive host. The home was beautiful and well stocked, made for a very comfortable stay. We absolutely loved the outdoor pool area and backyard - definitely a highlight!

Private room in Sag Harbor

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

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!

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.

4.95 out of 5 average rating, 63 reviews

Flat in Sagaponack

Hamptons Elegant and Comfortable Apartment

QuentinRating, 5 stars9 months ago

We had a pleasant stay at Cinthya and Holger. What a peaceful place, it felt like a retreat. Thank you for the flexibility, we will be back!

5 out of 5 average rating, 20 reviews

Cozy Get Away Sag Harbor Village Studio

CassRating, 5 stars10 months ago

H was sooo kind and thoughtful. She kindly welcomed us and offered privacy. H's place was exactly as described and sooo cozy. I hope to return. Thank you so much!

5 out of 5 average rating, 8 reviews

Flat in Southampton

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.