Cottage vacation rentals in Amagansett

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Top-rated cottage rentals in Amagansett

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Guest favorite

Cottage in North Fork

4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Guest favorite

Cottage in Westhampton Beach

4.93 out of 5 average rating, 164 reviews

Cool Tiny Cottage Artist Loft!

He Loved All Things Sea & I Followed Suit. 38 Years Ago My Father Built This Very Special Artist Loft Cottage Retreat. This Tiny Home is One Of A Kind. Throughout The Years Guests & Family Have Come & Gone Creating Beautiful Memories. The Space Is Tranquil, Serene, Peaceful & Harmonious. It’s A Wonderful Romantic Space, Charming For Family Gatherings, or One For A Soul Heart In Transition. All Have Found Passion, Peace and Progress Here. The Cottage Boasts A Fully Fenced In Large Yard, Deck, Grill, Light & Airy Vaulted Ceiling In Living Room With A Chenille Slip Cover Queen Sleeper and Cool Lounger With Library Bookcase With Books And Stereo/CD/Cassette, Color TV & DVD. Staircase to Loft Full Bed & Cute Twin Bed Area. Very Clean & Decorated Adorably. Wifi. Linens & Kitchen equipped, Washer/Dryer. Dining Table for 4 W/Sliders to Deck. Outside Seating for 6 & A Gas Grill. Perfect Place for 2. Quiet At End Of St. 1.5 miles to Rogers Beach Dune Rd/Ocean. 1 Mile To Main Street Village. 15 min to North Fork Wineries & Farms. Agent owned.

Top guest favorite

Cottage in Montauk

4.92 out of 5 average rating, 159 reviews

Montauk Cottage Escape

EH Town Rental Registry #: 23-483 MINIMUM STAYS REQUIRED Updated, spacious and comfortably furnished home in Montauk. Well situated to get you most places on foot or bike. Less than 10 minute walk to town, beaches, restaurants, nightlife. Walk to Sole East where you can enjoy use of pool and have lunch or a cocktail. Great place to enjoy your time in Montauk. Additional nightly fees apply for 5th guest. Pets considered with prior owner approval (Dogs ONLY). Additional Pet Fee applies.

Top guest favorite

Cottage in North Fork

5 out of 5 average rating, 31 reviews

Renovated 2-Bedroom Cottage on the North Fork

Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 132 reviews

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!

Top guest favorite

Cottage in Hampton Bays

5 out of 5 average rating, 31 reviews

walk to bay, woods cottage

Modern, picturesque cottage is situated atop a secluded and wooded 1/2 acre lot, with views of Peconic Bay and Squires Pond. The neighborhood is quiet and family oriented, with a 5 minute walk to a great bay side beach with a “lazy river”. Within a walk, bike ride or short drive are nature preserves with wooded trails for hiking. The cottage is the perfect distance from the south forks oceans and the north forks farms and vineyards. Pets are welcome for a nightly fee of $75

Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 100 reviews

Secluded 1Br cottage on the lake, close to Ditch

This is the best of Montauk living, right by the lake, close to Ditch, and with an incredible, lush front yard suitable for outside dining or having a couple friends over for dinner. Walk down to the lake to enjoy the sunset, or stroll over to the Crow's Nest for drinks or dinner. No need to drive, it's well within walking distance. Join the many that have experienced the magic of our cottage at South Lake.

Top guest favorite

Cottage in Montauk

4.88 out of 5 average rating, 239 reviews

Waterfront Cottage, Fort Pond MTK

Perfect cottage perched above Fort Pond with epic views and relaxed bohemian vibes. The cottage is private with a private deck on shared grounds with a fire pit, hammocks, paddle boards, kayak, and lake access. The grounds are expertly landscaped and take full advantage of fort pond views. We do live on the property full time and enjoy making our space a safe and clean environment.

Guest favorite

Cottage in Hampton Bays

4.91 out of 5 average rating, 124 reviews

Hamptons cottage just steps from the beach.

Bright, airy 3 bedroom classic Hamptons cottage less than a block from bay beach which is perfect temp and temperament for swimming, wading, paddleboarding and kayaking. Sunsets over the Peconic Bay are amazing especially when you do it with a cold beverage at Tiki Joe’s which has food, drink and fun bands every summer night—only a short stroll away.

Top guest favorite

Cottage in East Hampton

4.97 out of 5 average rating, 315 reviews

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).

Superhost

Cottage in Sag Harbor

4.87 out of 5 average rating, 102 reviews

Secluded Hamptons Cottage

This cottage has high ceilings, is bright and airy, has a wrap around deck with a great overhang for hanging out in the shade or sun. You can not see a neighbor. It has been described as “an adult tree house.” Just a fun and relaxing place to be. It is on over an acre of rustic property. Perfect for watching wildlife.

Top guest favorite

Cottage in Shelter Island

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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What guests are saying

Charming Scandinavian Inspired Beach Cottage

4.98 out of 5 average rating, 65 reviews2 weeks ago

Had a lovely time at Daniels adorable rental! The space was bright, airy and cozy. Loved the kitchen setup and open living area. The place was thoughtfully designed, the location was less than 10 minutes from downtown Sag Harbor. Only wish the weather was better, the beach is a 2 minute walk from the house! We'll most certainly be heading back!!!

Cottage in Sag Harbor

What guests are saying

Charming Cottage in Sag Harbor

5 out of 5 average rating, 20 reviews1 month ago

Laurie and Bob are fantastic hosts. The guest house at the back of their property is compact and deluxe. Great kitchen supplies and set up, clean fresh bathroom with nice toiletries. Comfy bed and bedding. Feels private. Convenient short drive to Sag Harbor. Friendly hosts, ready to help. Cant wait to go back.

Cottage in Sag Harbor

What guests are saying

Newly built cottage near the bay and hamptons

5 out of 5 average rating, 19 reviews2 months ago

I had a wonderful stay at Susan’s cottage. Check-in was easy, the cottage was gorgeous, clean, updated and fully stocked. Susan was a warm and friendly host who periodically messaged me to make sure all was ok during my stay. She also responded very quickly and was easy to get in touch with. I had a relaxing and quiet weekend away at Susan’s lovely cottage and would rebook with Susan again in the future. Loved every minute of my stay!

Cottage in Remsenburg-Speonk

What guests are saying

Modern Southampton Cottage | Heated Pool & Peloton

4.95 out of 5 average rating, 84 reviews1 week ago

I had a wonderful stay at Chris’s Southampton home! The house was spotless, beautifully maintained, and had everything I needed for a comfortable visit. Chris was an exceptional host—his communication was clear, timely, and super helpful throughout the entire stay. You can tell he truly cares about his guests’ experience. I’d absolutely stay here again and highly recommend this Airbnb to anyone visiting the area!

Cottage in Southampton

What guests are saying

Cozy Sound-side Cottage steps from beach

4.87 out of 5 average rating, 92 reviews4 months ago

We had a great experience staying at Melissa’s cottage and would happily recommend it to anyone else! We were in town from Florida visiting family in Rocky Point for Christmas and chose Melissa’s property as our place to stay. Melissa was very communicative, check in was super easy and we felt right at home on her property. Would definitely consider staying here again. Thanks Melissa!

Cottage in North Fork

What guests are saying

Scrimshander House

5 out of 5 average rating, 71 reviews7 months ago

Stephen's place was beautiful, well-equipped with everything we might have needed during our stay, very clean and comfortable. There were nice touches everywhere like the Aesop soap and shower products. The garden was also very pretty and peaceful, and set up well with lovely outdoor furniture. Stephen was also an incredibly helpful host - very responsive to requests and messages, and the instructions/recommendations we received before check in were probably the most helpful I've ever received! I very much recommend Stephen's place!

Cottage in North Fork

What guests are saying

A Cheerful 2 - Bedroom Cottage

4.97 out of 5 average rating, 29 reviews7 months ago

Our family of four was in the area for a wedding. The house was adorable and chock full of amenities. Milk, butter, cream cheese and bagels in the fridge. And bottles of water, in the fridge and next to the bed. There were bundles of towels , beautifully folded for each person. Snacks in a basket in the living room. The bathroom was fully equipped with all necessities. Board games galore and so beautifully presented. Only 10 minutes from the wedding venue and very close to a few farm stands. We would definitely stay again.

Cottage in North Fork