Vacation rentals with a fireplace in Amagansett

4.95 out of 5 average rating, 232 reviews

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.

4.94 out of 5 average rating, 154 reviews

A charming cottage is set within a lush green landscape, framed by trees. Sag Harbor Cove is visible in the background, showcasing a serene waterfront view. The grounds are spacious, providing an inviting atmosphere for relaxation or artistic inspiration.

Apartment in Sag Harbor

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".)

Superhost

A serene outdoor space features a heated saltwater pool surrounded by gray paving stones. Five lounge chairs with colorful cushions are positioned under large umbrellas, overlooking a lush green backyard with trees and hedges, enhancing the peaceful setting.

4.86 out of 5 average rating, 206 reviews

Walk2Beach, HeatedSaltWaterPool, Yard4Dog, Welcome

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Guest suite in East Hampton

A spacious pool area features a large swimming pool surrounded by a wooden deck. Lounge chairs are positioned along the perimeter, with vibrant flowers enhancing the outdoor setting. A decorative lamp provides soft lighting, while trees and greenery offer a natural backdrop.

4.99 out of 5 average rating, 135 reviews

Hamptons Dream Suite

Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also at TV and blue Ray player in the bedroom.

4.93 out of 5 average rating, 110 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

5 out of 5 average rating, 12 reviews

The kitchen is bright and airy, featuring white cabinetry and modern appliances. A round wooden dining table with a vase of yellow flowers sits in the center. Natural light is allowed in through a skylight, contributing to the inviting atmosphere.

Home in Amagansett

Amagansett walk-to-the-bay Beach House

Escape to this idyllic Amagansett cottage with inviting views of the peaceful Napeague Bay. Across from Fresh Pond estuary and bordering a reserve out the backyard, our perfectly quiet home is in a world unto itself away from Hamptons traffic. Cozy fireplace, sunlit rooms, and an outdoor 2-person soaking hot tub under the stars await. Watch sunrise over Montauk, cycle 10-min to town (or 15 to an ocean beach), explore wooded trails across the street, and paddle on the open bay.

4.93 out of 5 average rating, 14 reviews

Home in Amagansett

Amagansett, Waterfront retreat

(4 night minimum) Perfect place for a family, couple, or friends. Close to Amagansett Village and 12 minutes to Montauk, this waterfront retreat is great for nature activities like windsurfing, kiteboarding, sailing, stand-up paddle board, hiking, biking, and much more. Located just minutes from ocean beaches and 3 minutes to the "Napeague stretch", home to the famous "Lobster Roll" a/k/a "LUNCH" and the Napeague Clam Bar restaurants. East Hampton registry RR 25-417

Guest suite in East Hampton

A clear, inviting pool is framed by a spacious patio area. Four blue lounge chairs with vibrant green and white cushions are positioned alongside the pool, providing a relaxing space to enjoy the outdoors. Lush greenery and colorful flower pots enhance the surrounding ambiance.

4.96 out of 5 average rating, 163 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.

Four lounge chairs are arranged under large umbrellas, providing shade beside a serene pool area. The colorful cushions on the chairs complement the lush green landscaping, which features diverse foliage and natural textures, enhancing the outdoor relaxation space.

4.98 out of 5 average rating, 130 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

Guest suite in Sag Harbor

An inviting outdoor sitting area features wooden chairs positioned near French doors. The space is surrounded by lush greenery, and a stone pathway leads to the entrance of the studio apartment. Flowering vines and potted plants add a touch of nature.

4.89 out of 5 average rating, 352 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.

Superhost

A calm beach scene is depicted, featuring light sand stretching along the shore. Gentle waves approach the beach under a cloudy sky. A small boat is visible in the distance, while colorful umbrellas can be seen on the left, indicating a gathering of beachgoers.

4.63 out of 5 average rating, 94 reviews

Sun-drenched retreat with private beach pass

A peaceful oasis nestled in the best part of East Hampton Springs. Surrounded by enormous oak trees, less than a mile to the bay beach, 10 mins to the ocean, our 3 bedroom, 2 bathroom home is perfect for quality time away with friends and family. With a fully stocked cook's kitchen, contemporary art lining the walls, comfy couches, a vintage record collection, a fireplace, bbq & outdoor fire pit for s'mores and hangs, you won't want to leave!