Vacation rentals in Sagaponack

Chic w/ large pool ~ 1 block to waterfront dining

Serene, chic Hamptons oasis! Located 1 block from waterfront dining + 8 mins to beaches + Main St. Enjoy your large private home nestled in nature, perched back on a quiet tree lined street. Swim in your pool, spark up the BBQ + firepit under the starry sky! Cook in your Chef's kitchen + stream on the 80' TV. Walk 1 block to waterfront dinner + cocktails watching the best sunsets. Enjoy morning coffee on the sea. Walk back home in 4 minutes. You'll be 8 minutes to Main St., beaches + more!

Location · Family · Pool

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.

Value · Location · Getting around

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 · Condition

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

Location · Family · Beach

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.

Value · Family · Indoor spaces

Beachglass Barn Gated prvt pool King suite 2 bths

Clean beautiful bright King suite w/cozy Fireplace 2 full ensuite Baths & private separate Poolside Entrance. Pool is URS alone! We are just mins to beaches, shopping, golf, hiking, biking, yoga, eateries and wineries. Solo travelers are 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. Enjoy coffee/tea/treats

Value · Location · Beach

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 · TV

Hamptons Waterfront Getaway – Stylish & Serene

Waterfront Luxury Retreat in Sag Harbor. As featured in Vogue, 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.

Location · Family · Outdoor spaces

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.

Location · Family · Breakfast

Cottage 3 minute walk Bridgehampton town

Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. Depending check in/out flexible. 5min. drive or less 10 min. Bike to Hampton classic. Fenced backyard. Near Hampton jitney, train. Walk to town,fitness, bike to the ocean rd. beach. Same road of nature reserve, kids museum, farmers market. 5 min. drive to commons. Grill,Bikes,beach chairs+toys,Yoga mats, SUP Boards. $50+pet fee- number, size,duration of stay.

Family · Location · Accuracy

Peaceful Suite w/Pool, Hot tub, Private Entry.

A peaceful private suite in East Hampton’s Northwest Woods. Enjoy your own entrance, access to the pool, hot tub, and sauna, and easy access to beaches, town, and everything the Hamptons has to offer. Perfect for a relaxing getaway, whether you’re here for the beaches, a wedding, work, a quiet escape, or to explore the Hamptons.

Value · Location · Cleanliness

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 · Family · Layout