Cottage vacation rentals in Oyster Bay

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Oyster Bay

Guests agree: these cottages are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

The cottage is set against a vibrant sunset sky, showcasing hues of orange and pink. Lush greenery surrounds the home, emphasizing its cozy exterior. A stone pathway leads to the entrance, framed by trees, creating a welcoming scene.

Cottage in Westport

5 out of 5 average rating, 68 reviews

Wild Rose Cottage (Westport, CT)

Luxurious newly-renovated Cottage in prime location in Westport's historic district. Studio with queen-sized bed, kitchen (w/fridge, dishwasher, stove, oven, toaster, Keurig), full bathroom, A/C, fireplace, W&D, TV, WiFi (w/Amazon Fire Stick). Parking for one car. Back-up generator. Within stone's throw of Hudson Malone, Outpost Pizza, Merritt Country Store, Coffee An' Donut Shop and Grapevine liquor store. Just a short stroll on the sidewalk to downtown Main Street's shops and restaurants.

Top guest favorite

A charming cottage with a stone chimney and a sloped cedar shingle roof is depicted. The entrance, framed by neatly trimmed hedges, features two white doors, inviting guests. Surrounding trees provide a natural backdrop, and a gravel driveway leads to the entrance.

Cottage in Bedford

5 out of 5 average rating, 81 reviews

Clover Cottage

Our beautiful cozy cottage has lots of character and charm: stone foundation, old stone fireplace, cedar shingle roof and large eat-in kitchen. Large living room with french doors opening to a sizable deck. Upstairs is a bedroom with a king bed and bathroom. The best feature of the cottage is the location: we are right in Bedford Village - guests can walk to restaurants, shops, the Bedford Playhouse, the library and post office. Located 10 minutes from Metro-north and a 1-hr drive from NYC.

Guest favorite

A private backyard is depicted, showcasing an expanse of green grass bordered by various trees. Pink flowering branches gently frame the scene, adding color against the soft evening light. The side of the cottage is partially visible, blending harmoniously with the natural surroundings.

Cottage in Leonardo

4.94 out of 5 average rating, 140 reviews

Cozy Cottage Retreat on North Jersey Shore

Come and relax in our shore retreat cottage with private driveway and backyard a block from the sea. We are a retreat away from the hurly-burly of connected life, but we do have WiFi Internet. We are located in a safe quiet neighborhood 5-10 minutes walk from Leonardo state marina and beach, 2 miles from Atlantic Highlands with it's bustling main street and delightful harbor where you can take the Seastreak ferry to Manhattan; 15 minutes drive to Sandy Hook and the Atlantic Shore Beaches.

Top guest favorite

Adirondack chairs are arranged around a fire pit, surrounded by a lush forest of trees. A pathway can be seen in the background, leading to a light-colored building nestled among the greenery.

Cottage in Weston

4.96 out of 5 average rating, 120 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Guest favorite

A wooden staircase with a natural stone wall serves as a focal point in the entryway. Light hardwood flooring extends throughout the area, complemented by a table adorned with decorative items and a small plant. Soft lighting enhances the space's welcoming ambiance.

Cottage in Milford

4.95 out of 5 average rating, 315 reviews

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Top guest favorite

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Top guest favorite

Cottage in Milford

5 out of 5 average rating, 13 reviews

2BR Beach Escape Near Yale, NYC Train

Charming Milford Cottage-Your Coastal Escape-Beach, Town and NYC Train! This adorable cottage is perfect for a getaway, visiting colleges or traveling nurses. Enjoy a day on the beach (5 min walk), shopping/eating downtown or take the train into NYC (15 min walk). Start your day with a cup of coffee on the front porch rockers or cook a delicious meal in the well-equipped kitchen! Super cozy and charming...we can't wait to welcome you! Absolutely no parties permitted.

Top guest favorite

A charming yellow exterior showcases a welcoming entrance to the cottage. The outdoor patio features a black dining set with an umbrella, surrounded by vibrant greenery and a well-maintained lawn, providing a pleasant space for relaxation and gatherings.

Cottage in Milford

4.99 out of 5 average rating, 120 reviews

Walk 2 Beach + Tyde Venue |3BD Cottage w/ Fire Pit

Steps from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom, 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, our modern farmhouse-style home features a full kitchen, a private backyard with a fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and end the day by the fire. Comfort, style, and location — all in one unforgettable stay!

Top guest favorite

A quaint cottage is nestled among vibrant trees, showcasing rich foliage in shades of green and burgundy. A well-kept lawn surrounds the cottage, with a white door framed by flower beds. The serene setting invites relaxation in a natural environment.

Cottage in South Salem

4.96 out of 5 average rating, 231 reviews

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

Guest favorite

A cozy studio space is presented, featuring a spacious bed with dark cushions, a small dining table and chairs, and a comfortable couch. Light walls are complemented by decorative artwork and accents. A kitchenette area is visible, along with shelving and a TV, creating a functional living space.

Cottage in Centerport

4.93 out of 5 average rating, 128 reviews

NYC/Long Island - cozy garden cottage!

Sweet garden cottage - enjoy beautiful fall colors or spring blossoms away from the City! Sunny, bright, quiet, nicely decorated, completely private. Quiet, green neighborhood, a short walk from two Long Island Sound beaches. Private entrance and parking, private bathroom with shower, kitchenette, fridge, microwave, A/C, heat. Minutes from the train station to New York City; beautiful Long Island beaches nearby.

Top guest favorite

An inviting entrance showcases rustic wooden walls complemented by a welcoming staircase. A simple stool is positioned next to the door, while a television is mounted above a small radiator. Natural light filters through a nearby window, casting a warm glow on the wooden flooring.

Cottage in Patchogue

4.94 out of 5 average rating, 233 reviews

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Superhost

A wide wooden boardwalk extends along a sandy beach, framed by gentle waves in the distance. Benches are spaced along the path, providing views of the horizon. A viewing telescope stands prominently on the boardwalk, inviting guests to take in the coastal scenery.

Cottage in Kings Park

4.8 out of 5 average rating, 174 reviews

Cozy Riverside Cottage

This is a private cottage on its own lot with its own driveway and yard located in a quiet residential neighborhood. Several grocery stores and restaurants for delivery/pick up in the area. 400 MBPS Internet connection for those who need a reliable internet connection for work/movie streaming! Please note guest maximum is 4. There are no additional guests or visitors allowed.