Holiday rentals in Bridgehampton

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".)

Cheerful 3 bedrm-4 beds-3 bath -beach home w pool

Heart of the Hamptons is situated this bright, beach house 5 min 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 (add charge) pool (MD-mid Sept) and palatial lawns with room to roam. Keep it simple at this peaceful and centrally located getaway

Hamptons Elegant and Comfortable Apartment

Enjoy your stay in this beautifully decorated and completely private basement apartment - with all original artwork- in the center of the Hamptons with the added convenience of being close to major towns and beaches. Large bedroom with comfortable king sized bed and high quality mattress and linen. Large-screen smart TV with many channels. Closet space, well equipped kitchenette, bathroom with glass-enclosed shower. Seating area for 4 and second large-screen smart-TV with comfy oversized couch.

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

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!

Head of Pond House - Waterfront Cottage

Welcome to the charming, waterfront Cottage at Head of Pond House! Enjoy a peaceful retreat with beautiful lake access year-round and pool access from Memorial Day to October. The cottage features two comfortable king beds, including one in a cozy loft area, a full bath, WiFi, a projector for movie nights, and a fully stocked kitchen. Whether you’re looking for a relaxing escape or a comfortable base to explore the Hamptons, our waterfront cottage is the perfect spot for your getaway.

Designer home in Sag Harbor : 5BR walk to beach

Nestled in Sag Harbor, this elegant 5-bedroom home offers a saltwater heated pool just 2 miles away from the town. A mere five-minute stroll takes you to the Serene Green local farm stand and Long Beach Bay, where you can indulge in swimming, paddleboarding, and witnessing breathtaking sunsets. The chef's kitchen is perfect for culinary adventures, and you can savor your meals either poolside under the charming string lights at the 8-person farm table or indoors at the 8-person table

Hamptons Waterfront Getaway – Stylish & Serene

Waterfront Luxury Retreat in Sag Harbor. As featured in Mansion Global and Homeworthy. This serene designer home offers direct bay access for kayaking and paddle boarding, plus a private path to Clam Island for peaceful walks and beach picnics. Enjoy a gourmet kitchen with Viking and Sub-Zero appliances, spa-like en-suite baths, and plush bedding. Minutes to bay beaches and Sag Harbor village—your private escape awaits. Ideal for romantic getaways, relaxing weeks, or a summer reset.

Brand New Sun Filled Home

OUR HOUSE A beautiful newly renovated Southampton two story home with spectacular light, offering the best of indoor-outdoor living. A large deck off of the kitchen with small porches off of two primary suites and a small sitting area off the first floor junior suite. On almost one acre of land, there is plenty of peaceful space. Very central - two miles from the beach and town. Two car garage with built in electric vehicle charger. Gas fireplace. All appliances are brand new.

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.

Steps to Train, Dining & Beach US Open Golf

SOUTHAMPTON HOUSE NEW YORK charming cottage escape with a separate guest house, perfect for 7 guests. Relax in our private courtyard, complete with an outdoor kitchen with green egg, and fireplace for cozy nights under the stars. Just steps from the LIRR and walkable to downtown’s boutiques, restaurants, and attractions, our location is unbeatable. We’re just 2 miles from Coopers Beach.

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.