House vacation rentals in Wainscott

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

4.95 out of 5 average rating, 251 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.

4.91 out of 5 average rating, 122 reviews

Tranquil I Large pool 1 block to waterfront dining

Escape to your chic, serene Hamptons oasis! Enjoy the privacy of your own home just steps to waterfront dining + more Relax poolside, spark up the BBQ + firepit under the starry sky, swim + enjoy the peace + tranquility of this property. Enjoy easy living + convenience; walk 1 block to waterfront dining + cafe. Sip cocktails while you watch the most magnificent sunsets + have morning coffee on the sea. Stream on your 80' TV You'll be 8 minutes to Main St, shopping, beaches, restaurants + more!

A flower-filled back deck is highlighted by comfortable seating arrangements and a small dining table. Potted flowers in vibrant colors complement the wooden decking, while a table reflects the surrounding greenery. Various lounge chairs invite relaxation in this serene outdoor space.

4.9 out of 5 average rating, 112 reviews

Walk to Village Sag Harbor Victorian

Charming 2 bedroom 2 bathroom house in the historic Village of Sag Harbor with view of pond and park. Walking distance (not driving) to the quaint village with restaurants, shops, long wharf, gym, yoga. Living room with fireplace, dining room, kitchen and office. Upstairs loft ensuite bedroom and bathroom. Downstairs bedroom and full bath with tub and shower. Flower filled back deck with BBQ. Wireless internet, 2 TV's, air conditioner units, washer dryer. Minutes to ocean and bay beaches.

4.84 out of 5 average rating, 135 reviews

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!

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

4.98 out of 5 average rating, 137 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. (No AI used in these photos!)

A contemporary house exterior features a combination of wood and metal finishes, set against a backdrop of lush greenery. Large glass windows provide ample natural light, and a pathway of stepping stones leads through a manicured lawn, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 157 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

4.92 out of 5 average rating, 127 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.

4.96 out of 5 average rating, 106 reviews

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Modern Farmhouse Oasis | Private Pool | Near Hamptons & North Fork Escape to a stylish sanctuary where modern design meets pastoral charm. Set on a private, one-acre land, this farmhouse is a masterclass in coastal living. Enjoy sun-drenched lounge areas, a sparkling pool, and the constant, cooling luxury of Atlantic breezes. Inside, the home offers a seamless blend of contemporary interiors, and high-speed Wi-Fi—perfect for a peaceful retreat or a "work-from-anywhere" getaway.

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

4.83 out of 5 average rating, 126 reviews

East Hampton Oasis - Pool and Hot Tub

Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

A cozy bedroom is shown, featuring a spacious bed adorned with a floral quilt. Light streams through multiple windows, illuminating the room. A white dresser and closet are visible, while a green yard can be seen through the windows.

4.82 out of 5 average rating, 139 reviews

Sunny & Serene Private Cottage near Downtown EH

Our lovely one-bedroom cottage sits on a quiet lane 3/4 of a mile from downtown East Hampton. The cottage is light and bright, with whitewashed walls, vaulted ceilings and skylights, lots of windows and beautiful minimalist décor. It's an incredibly peaceful place to wake up in the morning, with a gorgeous green yard right outside the many bedroom windows. Every bay and ocean beach around East Hampton is 5-10 minutes away and Nick and Toni's is less than a 10 minute walk.

4.93 out of 5 average rating, 137 reviews

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

@WaterMillBeachBarn Dog friendly (upon approval) Hampton Beach Barn with pool and infrared sauna. POOL OPEN - May 1st - October 23, 2026 US GOLF OPEN 2026 - 5.6 miles from Shinnecock Hills Golf Club This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic designer decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

A cozy living area is highlighted by a chandelier, providing soft illumination. Two stylish chairs flank a round table, while a decorative sculpture and a vintage fireplace enhance the space. Large windows allow natural light to fill the room, offering views of the surrounding greenery.

4.89 out of 5 average rating, 108 reviews

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

Popular amenities for Wainscott house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.97 out of 5 average rating, 212 reviews

Private Oasis W/Stunning Vinyard and Pool Views

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

4.88 out of 5 average rating, 130 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

A modern home is set within a lush green landscape, surrounded by trees. A fenced saltwater pool is featured in the foreground, accompanied by several lounge chairs on a bluestone patio. The house is constructed with a mix of white siding and large windows, adding to its welcoming appearance.

5 out of 5 average rating, 18 reviews

Sunny Saltbox in Wainscott

A two-story home features a welcoming front porch with steps leading up to it. A gravel driveway is visible, bordered by lush greenery and flowering bushes. Bicycles can be seen propped against the house, surrounded by a peaceful, natural setting.

4.74 out of 5 average rating, 101 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

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.

4.98 out of 5 average rating, 100 reviews

Brand new house with an all year round hot tub.

An open living area features a large, neutral-toned sectional sofa and two black accent chairs, arranged invitingly on a light-colored rug. A skylight provides natural light, and vertical blinds partially cover the windows. A neutral coffee table sits in the center, complemented by a modest side lamp.

4.94 out of 5 average rating, 47 reviews

Sparkling East Hampton Oasis 3/2, heated pool

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

4.93 out of 5 average rating, 122 reviews

Modern farmhouse w/ pool, beach, horses and winery

An aerial view of a backyard features a spacious wood deck surrounding a gunite pool. Comfortable lounge chairs are positioned near the pool, alongside a shaded area with an umbrella. The natural greenery provides a serene backdrop to the outdoor dining area.

5 out of 5 average rating, 50 reviews

Secluded Luxury: New Gunite Pool, Walk to Bay

Weekly house rentals

A charming single-story home is set amidst lush greenery, featuring a well-manicured lawn. A welcoming front porch is accessible via a set of stairs, and vibrant pink flowering shrubs add a touch of color to the exterior.

4.93 out of 5 average rating, 89 reviews

Charming-N-Cozy East Hampton

4.8 out of 5 average rating, 10 reviews

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

A living area features striped sofas and wooden furniture arranged for comfort. Shelves lined with books are visible in the background. Natural light fills the space through windows with shades, while a fireplace adds a classic touch to this welcoming space.

5 out of 5 average rating, 20 reviews

Charming Village Cottage

The heated saltwater pool is surrounded by lush greenery, creating a serene atmosphere. Colorful pool floats in the shape of a flamingo and palm leaves rest on the surface. A hammock is visible nearby, inviting relaxation under the dappled sunlight.

4.97 out of 5 average rating, 32 reviews

Chic & Spacious Designer Home, Heated Pool/Spa

A bright kitchen features white cabinetry and granite countertops, complemented by stainless steel appliances. A central island with seating provides a gathering space, while large windows allow natural light to fill the room. Wood flooring adds warmth to the overall aesthetic.

5 out of 5 average rating, 18 reviews

Relaxing Spacious House. *pets welcomed*

A serene outdoor space features a newly installed heated pool surrounded by a patio. The area is complemented by comfortable lounge chairs and lush greenery, providing a tranquil setting for relaxation. A wooden fence offers privacy, while manicured shrubs frame the pool.

4.9 out of 5 average rating, 80 reviews

Bright & Modern E Hampton Getaway w/ Pool & Spa

An open living area showcases a modern sectional sofa in shades of gray, complemented by a circular wooden table. A brick fireplace adds a warm touch to the space, while a kitchen area is visible in the background, featuring wood cabinetry and a dining table.

5 out of 5 average rating, 49 reviews

Bay Access Cottage + Pilates Gym

A serene waterfront scene captures a vibrant sunset, showcasing a blend of orange, pink, and purple hues reflected on calm water. A wooden dock extends into the water, while silhouettes of people can be seen engaging at the water's edge.

4.75 out of 5 average rating, 4 reviews

Sag Harbor Village Waterfront Cottage

Private house rentals

4.96 out of 5 average rating, 28 reviews

A stunning view of Hashamomuck Inlet is captured during sunset, with soft clouds reflecting warm hues on the water. A wooden deck leads to the waterfront, framed by grasses and small rocks, enhancing the sense of tranquility in this natural setting.

Home in Southold

North Fork Waterfront Escape · Sunset Views

4.8 out of 5 average rating, 40 reviews

East Hampton Sunny Heated Swimming Pool. Sunroom.

The image captures a spacious backyard featuring a heated swimming pool with a gentle waterfall. Surrounding the pool, lounge chairs are neatly arranged. A charming house with multiple windows and outdoor seating is visible in the background, complemented by mature trees and colorful flower beds.

5 out of 5 average rating, 11 reviews

Sag Harbor Hamptons hideaway

5 out of 5 average rating, 13 reviews

Home in Greenport

Beach Block Hideaway

A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.

4.93 out of 5 average rating, 98 reviews

Central Private Bridgehampton

A light and airy living room features a comfortable dark gray sectional sofa and a matching loveseat, arranged around a wooden coffee table. A textured area rug lies on the hardwood floor, while large windows brighten the space with natural light. A ceiling fan is visible overhead.

4.95 out of 5 average rating, 43 reviews

A chic renovated beach house!

A well-maintained outdoor pool area features a crystal-clear heated saltwater pool surrounded by smooth stone decking. Comfortable lounge chairs and a sectional sofa with colorful cushions provide ample seating, while umbrellas offer shade. Lush greenery and flowering plants create a serene and inviting environment.

4.97 out of 5 average rating, 69 reviews

Stylish Oasis, Gorgeous Pool, Private Beach Access

The image captures a serene sunset over the Long Island Sound, with warm, golden light reflecting on the water. Silhouettes of trees and rocky shoreline frame the scene, which features a blend of colorful clouds in the sky, creating a calming and peaceful atmosphere.