Vacation rentals in Sagaponack

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Location · Value · Wifi

New Bridgehampton Sag Harbor Hamptons Cottage

This exclusive modern cottage blends attractive architectural design with warm, inviting interiors, offering a private park like retreat just moments from the village's finest vineyards, restaurants, shops, & beaches. Family-friendly, work-ready and equipped with high speed internet. Ideal for small groups, families, or remote workers. Bridgehampton/Sag Harbor Attractions: Wolfer Estate Vineyard, Children’s Museum, Hampton Classic Horse Show, Bay Theatre, Long Wharf & Golf Clubs. Come and relax!

Location · Value · Accuracy

Whaling Captain Pierson's Apartment

Whaling Captain Pierson's Apartment 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 TOO and Whaling Captain Pierson's Cottage).

Family · Location · TV

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.

Family · Value · Laundry

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Value · Location · Hospitality

Beachglass Barn Gated prvt pool King suite 2 bths

Beautiful, bright, spacious King suite w fireplace, 2 en-suite bathrooms & private separate poolside entrance. Pool is 4 u only! We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Solo travelers feel secure here. 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 best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Value · Family · Pool

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!

Location · View · Nearby

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

Location · Walkability · Backyard

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. Strictly 2 person max. Not suitable for infants/children No pets - owner is allergic.

Family · Value · Hospitality

Pool Central Private Bridgehampton Home

Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. NOTE* Rest assured, as always, even more so now, our housekeeper is aware to put in the extra tedious clean needed for a happy healthy stay! 7 minute drive to Hampton classic or less 20 min bike ride. Restaurants, studio 89 gym, on same rd. Ocean+bay 5-10 min drive. Bike to 1 ocean Yoga/winery. Halfway to Sag Harbor+Bridgehampton. There is pet fee.

Family · Value · Wifi

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.

Location · Value · Sleep quality

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).

Location · Value · Sleep quality