Holiday rentals with a fireplace in Shinnecock Hills

A spacious living area features a navy sectional sofa adorned with patterned throw pillows. A white coffee table sits in the center, displaying magazines. Natural light fills the room through large windows, enhancing the cozy, beach-themed decor.

4.89 out of 5 average rating, 237 reviews

Nautical Cottage Near Beach, Wineries, Golf, Shops

Coastal themed cottage located in the center of The Hamptons. Super Hosts! Great WiFi. Bright & comfortable space! Cowfish/Canoe Place Inn closeby! Near WINERIES, BEACHES, GOLF, WATERFRONT RESTAURANTS, & SHOPPING. 4 bedroom areas 2 full baths & outdoor shower. Spacious backyard w/ fire pit & deck w/ string lights. Lot's to do each season for couples, friends, coworkers & families. Everything you need & want in a Hampton's home. Large screen TVs/Roku, Foosball. Access to loft bedroom by ladder.

Sleep qualityHeatingBeach

4.92 out of 5 average rating, 173 reviews

A charming view is displayed through a large window, overlooking a green lawn that leads to a serene waterway. A decorative piece resembling a swan rests on a small table, casting a soft shadow as sunlight streams in.

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".)

Sleep qualityHeatingLocation

4.96 out of 5 average rating, 55 reviews

A large outdoor pool is surrounded by lounge chairs and umbrellas, inviting relaxation. Well-maintained gardens and trees frame the area, with a spacious deck along one side. The bright blue sky enhances the tranquil atmosphere of this inviting outdoor retreat.

Home in Shinnecock Hills

Spectacular Southampton Retreat!

Experience a lifestyle of relaxation and create lifelong memories with loved ones. Imagine yourself lounging by the pool with your favorite drink, surrounded by beautifully manicured gardens that help you unwind and calm your mind and body. Located just beyond Southampton Village, south of the highway, our 1-acre estate features a spacious 4-bedroom, 2.5-bathroom home This property is perfect for a relaxing Hamptons getaway offering a large pool, comfy beds, sunroom, BBQ, fire pit + much more

Indoor spacesHeatingBathroom

5 out of 5 average rating, 26 reviews

Home in Shinnecock Hills

Dream Colonial with Heated Pool Southampton, NY

This picturesque abode boasts classic cedar shingle siding, exuding timeless elegance and charm. Conveniently situated south of the highway, this residence offers easy access to all the amenities of Southampton. Dive into relaxation and soak up the sun in your private pool oasis. Embrace the comfort of generous living spaces designed for relaxation and entertainment. Host unforgettable gatherings in the beautifully landscaped outdoor space, perfect for summer barbecues and al fresco dining.

Indoor spacesBeachPool

5 out of 5 average rating, 110 reviews

A lush backyard features a children's playset alongside a hammock. Adirondack chairs are arranged around a fire-pit, framed by trees and greenery. A serene waterfront view is visible, with a dock extending into the calm waters, enhancing the natural landscape.

Villa in Southampton

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Sleep qualityIndoor spacesNearby

An outdoor space featuring a saltwater pool with a jacuzzi positioned nearby. A patio area includes an umbrella and ample seating options. Lush green grass surrounds the pool, while two white decorative swan floats are visible on the water, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 59 reviews

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

Located in Hampton Bays just a 5 min drive to beaches, waterfront restaurants, wineries & golf courses. This vacation property offers an open concept single family home w/ 4 bedrooms, 5 baths, a spacious living room, an outdoor deck and patio with a table and chairs, pool, jacuzzi and a pool house! The pool is opened mid May - second week of October and can be heated at an additional cost. Located just 5min away from Hampton Bays town and 5min drive to one of our lovely beaches.

Sleep qualityIndoor spacesNearby

4.98 out of 5 average rating, 54 reviews

A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.

Home in Shinnecock Hills

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Chic, 5-bedroom, 3.5 half-bath home is close to the water and the village of Southampton. The sparkling pool has a beautiful backdrop of a lushly landscaped garden. Southern exposure in the backyard brings an abundance of sunshine inside and out. The home includes an outdoor sauna, fire pit and rock garden perched above the pool for your very own spa retreat. The inside of the home is thoughtfully designed with a relaxed, chic & luxury feel making it the perfect Hamptons getaway.

Sleep qualityIndoor spacesDecor

4.97 out of 5 average rating, 187 reviews

A spacious living area features high ceilings and natural light streaming through large windows. A white sofa is paired with wooden chairs, while a glass coffee table sits on a woven rug. An elegant dining area is visible in the background with a large table.

Cottage in Southampton

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Indoor spacesSleep qualityLocation

4.89 out of 5 average rating, 56 reviews

Cottage in Southampton

Enchanting Cottage in the Heart of Southampton Vil

Enchanting Cottage in the Heart of Southampton Village Escape to this delightful cottage nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, restaurants, and entertainment, this retreat boasts private gardens and access to a refreshing pool. 🛏️ Bedrooms: 1  🛁 Bathrooms: 1 🌳 Outdoor Space: Private gardens 🏊 Pool Access: Available (open MDW -LDW) 🚘 Two Parking Spaces

Indoor spacesSleep qualityHospitality

4.92 out of 5 average rating, 172 reviews

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

Home in Mattituck

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Indoor spacesSleep qualityBathroom

4.83 out of 5 average rating, 217 reviews

The living area is characterized by high vaulted ceilings and large windows allowing natural light. A sofa with light cushions is centered around a wooden coffee table on a neutral rug. A decorative fireplace is framed with a modern mantle, adding warmth to the space.

Home in Southampton

Stylish & Chic w hot tub/ Near Beaches & Village

Chic & cozy Hamptons retreat just minutes from Southampton Village and beaches! Enjoy a private backyard with sundeck, hot tub, fire pit, outdoor shower, and indoor fireplace. Next door to world-famous Shinnecock Hills Golf Club and 15 mins to Poxabogue public course. Close to Wölffer Estate, Duck Walk, and Channing Daughters wineries. Walk the nearby Scallop Pond Preserve or Elizabeth Morton Wildlife Refuge. Perfect year-round getaway!

Sleep qualityIndoor spacesCleanliness

Guest suite in Hampton Bays

A cozy outdoor seating area features four upholstered chairs arranged around a circular table. A red vase holds greenery in the center. A black grill and an umbrella are visible in the background, with a bamboo privacy screen enhancing the serene atmosphere.

4.95 out of 5 average rating, 129 reviews

Hamptons Cozy Cottage

My cottage for "2" or perfect for “1” (Are you a medical professional, or Golf caddy, tennis pro?) Perfect! We are just minutes to the Bay and Ocean beaches , Many great nearby restaurants, Charter boat/Sunset Cruise are within walking distance. The town is opposite direction 2 miles. North Fork 10 Miles: Shop: Tanger Outlets and Wineries, Breweries. Beach Chairs/Towels and Bikes are available upon request.

Indoor spacesSleep qualityAmenities

Popular amenities for Shinnecock Hills Accommodation with Fireplace

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fireplace

4.97 out of 5 average rating, 214 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

Sleep qualityIndoor spacesTV

4.98 out of 5 average rating, 224 reviews

A living room is featured with a stone fireplace as the focal point, surrounded by wooden cabinetry. Large windows invite natural light, and a mix of seating options includes a gray sofa and two blue chairs. A coffee table sits at the center, adorned with a decorative bowl.

Home in Sag Harbor

Sag Harbor home away from home

Sleep qualityHeatingKitchen

A bright living room features a light-colored sectional sofa accompanied by dark accent chairs. A glass coffee table sits in the center, showcasing various books. Natural light streams through large windows, revealing a view of the outdoors. Decorative elements include a wall-mounted TV and an ornate cabinet.

4.96 out of 5 average rating, 57 reviews

Sophisticated and Sweet

Sleep qualityHeatingHospitality

Home in Westhampton Beach

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

4.97 out of 5 average rating, 108 reviews

Brand new house with an all year round hot tub.

Sleep qualityIndoor spacesCleanliness

5 out of 5 average rating, 13 reviews

Hamptons Retreat • Hot Tub • Minutes to Beaches

Indoor spacesAccuracyQuiet

4.96 out of 5 average rating, 55 reviews

An open-plan living area features a spacious dining table surrounded by black chairs. Natural light floods in through several windows and skylights, illuminating the modern kitchen equipped with sleek cabinets and stainless-steel appliances.

Home in Southampton

Renovated Southampton Home+Pool

HeatingSleep qualityAmenities

A spacious deck is furnished with comfortable seating and a dining table, overlooking a marina with various boats. The water reflects clear blue skies, creating a serene atmosphere. A patterned area rug adds a touch of style to the outdoor space.

5 out of 5 average rating, 30 reviews

2.5 Miles from the 2026 U.S OPEN, Waterfront

Indoor spacesSleep qualityBathroom

An open living space features a comfortable sofa adorned with patterned cushions, complemented by a light wood coffee table. A dining area with a round table is visible, and large glass doors provide access to the backyard, bringing in natural light.

4.93 out of 5 average rating, 128 reviews

Hamptons "Get Away" Near Beach/Wineries/Golf

Indoor spacesSleep qualityParking

Apartment rentals with a fireplace

4.96 out of 5 average rating, 73 reviews

A tranquil beach scene captures the shoreline with gentle waves lapping at the sand. The sky is painted with warm hues of orange and yellow as the sun sets on the horizon. The sandy beach showcases a serene and welcoming atmosphere.

Apartment in Shoreham

Lovely Loft Apartment with Private Beach Access!!

Sleep qualityIndoor spacesLocation

4.94 out of 5 average rating, 108 reviews

An open living space features a cozy seating area with a black futon, adjacent to a sleek TV stand with an electric fireplace. A small dining table is positioned nearby, and modern appliances are visible in the well-equipped kitchen with dark cabinetry.

Apartment in Centereach

1 Bedroom Apartment with Kitchen & Full Bath

Indoor spacesSleep qualityParking

4.98 out of 5 average rating, 118 reviews

Apartment in Norwalk

Brook Haven Home away from home!

Indoor spacesSleep qualityAmenities

Apartment in Shinnecock Hills

A cozy living area features wood-paneled walls and a neutral sofa positioned near a lamp and a chair. Natural light floods through the windows, illuminating a patterned rug on the hardwood floor. A television is mounted on the wall opposite the entrance.

4.93 out of 5 average rating, 14 reviews

Sugarloaf Annex

Indoor spacesCheck-inLocation

4.93 out of 5 average rating, 101 reviews

A modern seating area features a light-colored couch with plush cushions, complemented by a stylish black and white striped rug. Two round black coffee tables hold decorative items, and a vase with branches adds a touch of elegance. Natural light filters through sheer curtains.

Apartment in Bridgeport

Beautiful, clean and quiet place to relax

Indoor spacesSleep qualityLocation

4.88 out of 5 average rating, 155 reviews

A corner of the apartment features unique hand-tinted windows that create colorful reflections. A cozy armchair sits beside a fireplace, surrounded by potted plants. The space is complemented by a woven area rug and a light-colored bed with a simple texture.

Apartment in Bridgeport

Stylish Sheek Loft Ricport Studio 2, Downtown

Sleep qualityHeatingLocation

Apartment in Hampton Bays

A well-lit living area is highlighted by a cream-colored sofa with nautical-themed pillows. A wooden coffee table features shells and a vase of flowers. Display shelves in the background hold decorative items, with natural light streaming through large windows.

4.84 out of 5 average rating, 143 reviews

Vacation at the Beach: Entire Home

HeatingSleep qualityOutdoor spaces

Apartment in Center Moriches

An open studio space features a spacious bed with a light duvet and decorative pillows. A leather couch complements the area, while large windows provide natural light, framed by white blinds. A bedside table and warm lighting create a cozy ambiance.

4.81 out of 5 average rating, 122 reviews

Cozy Studio 15 Min From Hampton Beaches

Indoor spacesSleep qualityComfort

Villas with a fireplace

4.9 out of 5 average rating, 83 reviews

A modern outdoor space features a rectangular pool with crystal clear water, framed by a wooden deck. Comfortable seating arrangements, including two chairs with cushions and a dining table set for six, are complemented by an umbrella for shade.

Villa in Greenport

Year-Round Heated Pool Villa - 3 blocks from town

HeatingSleep qualityAmenities

Villa in Shinnecock Hills

A heated salt water pool is surrounded by a stone patio, reflecting sunlight on its clear surface. A Japanese Maple tree provides shade along one edge, enhancing the serene outdoor space. Lush green grass and a white fence enclose the area, creating a private setting.

4.95 out of 5 average rating, 77 reviews

Just renovated Southampton retreat w/ heated pool

Indoor spacesSleep qualityBathroom

4.82 out of 5 average rating, 17 reviews

An inviting living area features a stone fireplace accompanied by a large flat-screen TV. Colorful artwork and decorative accents include modern furniture and plush seating. Large windows allow natural light to fill the space, while a dining area is visible in the background.

Villa in Bridgeport

Indulge in Prime Luxury 3BR 3-7 Guest

Indoor spacesDecorLaundry

4.96 out of 5 average rating, 28 reviews

Villa in Hampton Bays

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

Indoor spacesSleep qualityLocation

4.9 out of 5 average rating, 39 reviews

The exterior of the house is framed by lush greenery, with a wrap-around deck highlighted by large windows. The warm glow from the interior lights contrasts with the natural surroundings, while the fieldstone chimney adds an element of rustic charm. A pathway leads towards the entrance.

Villa in Guilford

TREETOPS! An upscale, unique 5 bdrm home with POOL

Sleep qualityIndoor spacesFamily