Holiday rentals in Northwest Woods

4.95 out of 5 average rating, 233 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.

4.95 out of 5 average rating, 435 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

4.93 out of 5 average rating, 154 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

4.98 out of 5 average rating, 176 reviews

Flat in Sag Harbor

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

Guest house in East Hampton

4.82 out of 5 average rating, 319 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.

Superhost

4.84 out of 5 average rating, 100 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 September 24. The hot tub remains open year round.

4.94 out of 5 average rating, 187 reviews

Home in Greenport

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

5 out of 5 average rating, 13 reviews

Home in East Marion

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Guest suite in Sag Harbor

4.9 out of 5 average rating, 356 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

4.63 out of 5 average rating, 95 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!

5 out of 5 average rating, 10 reviews

Bungalow in East Hampton

Charming Bungalow on the Bay

This newly remodeled 1960’s bungalow is the perfect getaway for couples and families alike. Located right on Gardiner’s Bay, there’s a gorgeous view of the water from the large windows and front porch. From the front steps you can follow the 300 yard path to your own private beach where you can wade, swim, snorkel, paddleboard, or just enjoy the amazing view and salt air. (East Hampton Rental Registry Certificate Number: 24-234)

4.97 out of 5 average rating, 29 reviews

Villa in East Hampton

SERENITY AT SHOREWOOD Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

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Other great holiday rentals in Northwest Woods

5 out of 5 average rating, 24 reviews

Walk to village and hidden from the hustle EH home

Sneha SusanRating, 5 stars14 months ago

Victors place was warm and cozy - the perfect retreat from the hustle and bustle of everyday life. It was private and made us feel right at home. Victors house is well stocked with all the required supplies. They have the Monopoly - Hampton edition which made it fun while driving around the Hamptons.

Private room in Sag Harbor

4.96 out of 5 average rating, 216 reviews

Sag Harbor Home, Perfect for the Solo Traveler

MarcosRating, 5 stars2 weeks ago

Staying at Barbara’s was, without question, the best Airbnb experience I’ve ever had — and I’ve had some truly wonderful ones. From the moment I arrived, she greeted me with the warmest smile and a peaceful, welcoming energy that immediately made me feel at home. She had fresh cookies waiting for me, bottled water by the bedside, and made sure I had everything I needed to feel comfortable and cared for. In the morning, I woke up to the smell of fresh coffee and the most beautiful breakfast spread — homemade zucchini bread, muffins, fruit, teas, and English muffins — all lovingly prepared. Her home is immaculate, beautifully decorated, and so thoughtfully arranged. I had one of the most restful nights of sleep I can remember in her incredibly comfy bed, waking up completely recharged. And her cat? The cutest I’ve ever seen — gentle, friendly, and just added to the charm of the whole experience. Barbara is a truly exceptional host in every way. I left her home feeling so grateful, res

Home in Shelter Island

5 out of 5 average rating, 5 reviews

Designer Renovated Farmhouse with Pool

FrancisRating, 5 stars1 month ago

We really needed the solitude and my daughter and I had a fantastic rest. What a great place to hibernate in the winter! Great comfortable beds, well stocked kitchen In a beautiful space. It is a bird sanctuary with nice walks and brilliant cycling.

4.82 out of 5 average rating, 28 reviews

Historic East Hampton Home - Private Beach Access

KyleRating, 5 stars1 month ago

Elizabeth was a wonderful host - we traveled with a toddler and an infant and Elizabeth could not have been more accommodating. She was so responsive and friendly before and during the entire trip. The house and property are absolutely beautiful— you can’t beat being able to walk right down to the beach. Highly recommend!

4.97 out of 5 average rating, 72 reviews

Cedar Cottage

FrankRating, 5 stars9 months ago

Wonderful! We were looking for an end of summer getaway to relax and de-stress; the Cedar Cottage of East Hampton was a perfect fit. Very comfortable, well equipped kitchen, fun outdoor deck, great beach, easy access to Sag Harbor or East Hampton. Thanks for all!

4.6 out of 5 average rating, 15 reviews

4 Min Walk to the Beach!

LizetRating, 5 stars11 months ago

Beautiful Beautiful Amazing memories created Thank you so much!

4.9 out of 5 average rating, 20 reviews

East Hampton Secluded Escape with Gunite Pool

MartaRating, 5 stars2 weeks ago

The place was clean, spacious and cozy. Allen was quick to respond to our messages and concerns. Thank you for being a great host.