Vacation rentals in Wainscott

A classic two-story house with a wooden exterior is framed by neatly trimmed greenery. The front porch features a white gate, inviting guests. Views of the water and trees are visible in the background, suggesting a serene location.

4.93 out of 5 average rating, 149 reviews

Whaling Captain Pierson's Apartment TOO

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

An inviting living area showcases a combination of seating, including a chaise lounge, armchairs, and a wooden table. A television is positioned near a set of stairs leading to the upper level. Natural light enters through large windows, creating a comfortable atmosphere.

4.96 out of 5 average rating, 153 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Guest suite in East Hampton

A serene beach scene features soft, golden sand curving along the shore, meeting gentle waves that lap at the water's edge. The horizon showcases a calm, blue ocean under a sky filled with wispy clouds, creating a tranquil atmosphere.

4.79 out of 5 average rating, 185 reviews

Serenity Near the Beach

Perfectly situated near beaches, waterfront dining , town, and art sites. Peaceful private room and full bathroom with private entrance from outside. Equipped with everything you need to enjoy beach. Enjoy beautiful view of natural setting from deck. We provide microwave, coffee maker, mini refrigerator, dishware, and table in room and outdoors - does not include living room or kitchen. Perfect for work or vacation. Space attached to the house but 100% private. No smoking. No children.

A charming orange house with white shutters features a welcoming front entry. Four large windows, adorned with flower boxes, enhance the inviting appearance. Lush greenery surrounds the front yard, complemented by neatly trimmed bushes and a pathway leading to the entrance.

4.98 out of 5 average rating, 175 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Guesthouse in East Hampton

The kitchenette features a small refrigerator, microwave, countertop oven, and a Keurig coffee maker. A rack displays various coffee pods, and a paper towel holder is positioned nearby. Light-colored cabinetry provides ample storage space above the countertop.

4.82 out of 5 average rating, 316 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for guests. 2 Adult guests ONLY (no children) due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets.

Guest suite in Bridgehampton

A serene outdoor area features a saltwater pool surrounded by spacious stone decking. Lounge chairs are neatly arranged along the poolside, with trees providing natural shade in the background. A separate structure can be seen beyond the pool, blending seamlessly into the tranquil environment.

4.93 out of 5 average rating, 68 reviews

Bridgehampton New & Modern Design

Located about a mile away from downtown Bridgehampton and less than three miles away from downtown Sag Harbor. This brand new unit includes everything. Everything in this unit is brand new and of high quality. The unit has its own separate parking area and entrance and it totally private from the main house. POOL AND HOT TUB USE WILL BE AVILABLE FOR MOST OF THE YEAR, use of the pool and hot tub amenities will be made available. The pool is now open for the season as of March24.

A bathroom countertop showcases a washbasin alongside neatly stacked white towels. A decorative dish holds a bar of Dove soap, while a small bowl displays pink artificial flowers. A bottle of liquid soap and additional items are arranged in a stylish tray.

4.93 out of 5 average rating, 116 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

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.

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.

A bright kitchen area features white cabinetry and a sleek countertop, complemented by a large window and glass door leading to the outside. A dining table with two chairs is positioned nearby, and light wood flooring enhances the spacious atmosphere.

5 out of 5 average rating, 13 reviews

Spacious Apt. Walk to Beach!

This light-filled, airy apartment with a private entrance and reserved parking spot for one (more space if requested), is perfect for a couple or solo traveler. Just a 5-minute walk from the private beach where you can swim, paddleboard, kayak, etc., this is your perfect getaway! Main Street is accessible by foot in about a 25 pleasant minutes either by a walk on the beach or drive/bike down the road. See you soon :)

Guest suite in North Fork

A vibrant seasonal market is displayed, featuring a yellow vintage truck parked in the foreground. Colorful chrysanthemums and pumpkins line the gravel pathway, while a rustic building adorned with decorative elements stands in the background against a cloudy sky.

4.88 out of 5 average rating, 663 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

4.98 out of 5 average rating, 321 reviews

The kitchen features modern cabinetry and a black countertop, complemented by stainless steel appliances. Natural light floods in through three large windows, enhancing the bright ambiance. A tile backsplash provides texture, and the space is equipped with essential cooking tools for convenience.

Cottage in East Hampton

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).

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Popular amenities for Wainscott vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Wainscott

4.98 out of 5 average rating, 181 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in North Fork

Greenport Village walking distance to all

4.87 out of 5 average rating, 159 reviews

Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

Cottage in Shelter Island

Two wooden chairs are positioned on a grassy area overlooking the calm water. A fire pit sits in between the chairs, and a swing hangs from a nearby tree. In the background, a dock extends into the water, framed by trees.

4.97 out of 5 average rating, 108 reviews

Shelter Island Waterfront Getaway

4.89 out of 5 average rating, 490 reviews

Cabin in Rocky Point

Great little place just for a couple

Guesthouse in Shelter Island

A spacious outdoor area is highlighted by a refreshing pool surrounded by lounge chairs. The pool house, featuring a white exterior, sits in the background amidst lush greenery. Flower pots and garden plants frame the scene, enhancing the tranquil environment.

4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

4.98 out of 5 average rating, 44 reviews

A shaded porch is visible, featuring a round table with a floral tablecloth and several chairs. The tranquil ocean is seen in the background, while distant land can be discerned on the horizon. Soft light illuminates the space, enhancing the inviting setting.

Home in Woodmont

Beachfront paradise- come, stay, relax!

4.84 out of 5 average rating, 111 reviews

A charming cabin exterior features dark wooden siding and light-toned accents. Steps lead to a welcoming deck where a kayak rests alongside two spacious chairs. Large windows provide natural light, while surrounding trees create a serene atmosphere.

Apartment in Rocky Point

Cozy and Quiet space to Relax