Vacation rentals in Northwest Woods

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Top-rated vacation rentals in Northwest Woods

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Guest favorite

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

Home in East Hampton

4.95 out of 5 average rating, 448 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Superhost

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

Home in East Hampton

4.87 out of 5 average rating, 212 reviews

HeatedPool, Walk2Beach, FencedYard4Pup, Spotless

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

Superhost

A modern home is showcased with a unique angular design, featuring a combination of wood and glass. The surrounding lawn is spacious and well-maintained, with natural landscaping, including grasses and a small tree, contributing to the serene outdoor setting.

Home in East Hampton

4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

Guest favorite

An open-concept living space features a dining area with a rectangular wooden table adorned with a decorative bowl. A spacious couch is positioned near a fireplace, with large windows allowing ample natural light. A stylish chandelier hangs above, complementing the high, pitched ceiling.

Villa in East Hampton

4.99 out of 5 average rating, 100 reviews

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Top guest favorite

A spacious sleeping area is featured with a large bed adorned with a colorful blanket. Two bedside lamps are placed on sleek nightstands, and a full-length mirror leans against the wall. An entertainment unit with a TV is positioned opposite the bed, complemented by light wood flooring.

Apartment in East Hampton

4.95 out of 5 average rating, 22 reviews

Newly renovated, private studio.

Enjoy a tranquil, private retreat in a natural, rustic setting < 1 mile from 2 bay beaches, @ 5 miles from East Hampton, and @ 4 miles from Sag Harbor. This studio has a separate entrance with a deck and garden, an attached bathroom, a cooking alcove, a sitting area, a bar/work station, individual climate control and a Roku tv. The owners live on premises but often travel for work. While everything in this studio is brand new, the setting is fairly rustic—not your typical Hamptons mansion.

Guest favorite

A swimming pool with clear blue water is surrounded by a spacious deck. Lounge chairs with striped cushions are arranged for relaxation. Colorful umbrellas provide shade over outdoor sofas, and lush greenery in the background enhances the serene environment.

Home in East Hampton

4.93 out of 5 average rating, 158 reviews

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Top guest favorite

A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.

Apartment in Sag Harbor

4.98 out of 5 average rating, 187 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!

Superhost

Inside a spacious safari tent, a queen bed is neatly made, flanked by nightstands on either side. Sunlight filters through the large screened windows, offering views of the outdoors. A small chair and table set are positioned at the entry, providing a cozy spot to enjoy the scenery.

Tent in East Hampton

4.88 out of 5 average rating, 64 reviews

Safari Tent Glamping,S9-CedarPt, East Hampton, NY

LoveCedarPt - Explore the Hamptons & Montauk, Eat, Provision and Glamp in Comfort at the 607 acre Cedar Point County Park on Northwest Harbor near Sag Harbor & E. Hampton. Lodge overnight in comfort & style in our furnished platform Safari Tents in a perfect tree meadow on the bluffs overlooking the bay and Shelter Island with sunsets 2nd to none. For 2025, we have 16 tents with queen beds and linens. Tents are covered with large rain flies that make a covered porch for the Adiron

Superhost

A cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.

Guesthouse in East Hampton

4.82 out of 5 average rating, 324 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.

Top guest favorite

The sleeping area features a plush bed with white bedding and two neatly arranged pillows. Warm light from the wall-mounted lamps illuminates the space, while green foliage is visible through the large windows on either side, creating a soothing atmosphere.

Apartment in East Hampton

5 out of 5 average rating, 11 reviews

The Hideaway | Clearwater Beach

Your private retreat in the heart of Clearwater Beach, East Hampton! Escape to this serene, design-forward suite nestled in one of the most peaceful corners of the Hamptons. Just minutes from the bay, this luxury hideaway offers the perfect balance of comfort, style and convenience. The space features a plush king bed and all the amenities you need for a relaxing stay. Sip your morning coffee in your private outdoor space before heading off for a swim at Clearwater Beach.

Top guest favorite

A cozy sleeping area is highlighted by a spacious bed with light blue bedding, positioned near a working fireplace. A television is placed on a wooden stand across from the bed. Soft lighting from bedside lamps creates a warm ambiance, complemented by a decorative artwork on the wall.

Guest suite in Sag Harbor

4.9 out of 5 average rating, 368 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.

Top guest favorite

A private pool area is surrounded by lush greenery, providing a secluded retreat. The rectangular pool, featuring steps for easy access, is bordered by a brick patio. Lounge chairs are positioned around the pool, with planters adding a touch of color, creating a tranquil outdoor space.

Guest suite in East Hampton

4.96 out of 5 average rating, 170 reviews

Be our guest Central spot King en-suite 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/treats