Cottage vacation rentals in Oyster Bay

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Top-rated cottage rentals in Oyster Bay

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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, 67 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.

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

A serene outdoor setting features several Adirondack chairs arranged around a fire pit, surrounded by lush green trees and natural rock formations. The calm river flows gently nearby, with sunlight filtering through the canopy, creating a peaceful retreat atmosphere.

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 modern living area is highlighted by a natural stone wall and polished wooden flooring. Comfortable seating includes a leather sofa and a patterned ottoman. A dining table for four is positioned under large windows, allowing natural light to fill the space.

Cottage in Milford

4.95 out of 5 average rating, 314 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 scenic view of the river, showcasing lush green hills in the background and a collection of boats docked along the shore. A wooden deck is visible in the foreground, framed by a fence and greenery, inviting relaxation by the water.

Cottage in Sea Bright

4.95 out of 5 average rating, 131 reviews

Sea Bright NJ Cottage 1 block from BEACH sleeps 6!

RARE Off Street Parking for 4 compact cars or 3 SUVs This 3 bedroom beach cottage is a perfect, cost effective alternative to a hotel stay. Wifi, N64, HBO, Cable & board games for those rainy days. Fully furnished bedrooms, one bedroom has home office desk set up, living area, and kitchen, to our comfortable lounge area, BBQ, and outdoor shower. Perfect way to relax after a fun day at a beach, event, or exploring the beautiful town of SeaBright!

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 :)

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, 118 reviews

3BD Cottage Walk 2 Beach and Tyde Venue, Fire Pit

Be our guests! Stay at a cozy 3-bedroom, 1-bath retreat just steps from Walnut Beach in Milford, CT. This charming single-family home offers a modern farmhouse design, a fully equipped kitchen, and peaceful surroundings. Perfect for family vacations, romantic getaways, or visits to Yale University and nearby wedding venues. Enjoy privacy and comfort with easy access to the beach and local attractions. Book your unforgettable stay today!

Top guest favorite

A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.

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.

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 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.

Superhost

A small deck is featured with two light-colored Adirondack chairs positioned for outdoor relaxation. Tall greenery and trees provide a natural backdrop, creating a serene setting. The wooden deck is made of planks and is clear of any items, emphasizing the inviting space.

Cottage in Kings Park

4.8 out of 5 average rating, 173 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.

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What guests are saying

Rye Cottage - Walk to Beach & Playland

5 out of 5 average rating, 39 reviews1 month ago

Honestly cannot think of any way to improve on this place, which was perfect for our needs — and perfect for just about any scenario I can imagine. Well appointed, well located, and immaculate. I used to live in Rye, and felt immediately at home in every way. Just great.

Cottage in Rye

What guests are saying

Pristine cottage walk to beach

5 out of 5 average rating, 14 reviews31 months ago

The Cottage was Fantastic!! It greatly exceed my expectations! The quiet neighborhood and the distances to the beach was great bonus! And the Backyard was one of my favorite parts. And Cheryl was an excellent host who would check in and make sure everything was to my liken. I can't wait for my next visit!!

Cottage in Woodmont

What guests are saying

Charming beach cottage, newly renovated.

5 out of 5 average rating, 9 reviews7 months ago

Beautiful cottage in Bayville. We enjoyed our stay and felt right at home. Clayton’s house is within walking distance to beach, playground, and coffee shop. Clayton’s neighbors were very friendly and would greet us every morning. We felt very welcomed and plan to visit again!

Cottage in Bayville

What guests are saying

Beach Cottage with Breathtaking Water Views

5 out of 5 average rating, 8 reviews1 month ago

This house is in a great location. You can walk on the beach, walk or ride around the peninsula with little traffic. It's an easy walk to restaurants a good pizza place and deli. It's also a great starting point if you want to explore the CT coast or head into NYC. The train is a 10 minute drive away. Or if you are trying to get away from it all, it's a quiet, safe place to rest and rejuvenate. It's a hidden gem on the mid CT coast area.

Cottage in Lordship

What guests are saying

Bright and Airy Cottage in Bellport Village

4.94 out of 5 average rating, 16 reviews34 months ago

This house is wonderful. Great location, close to town. It is so peaceful and lush. The pool was very relaxing and just the right temp. Great notes around the house to help with finding things or to know what to do/not do. Very well thought out. Joshua and Brian were easy to communicate with about the rental. We are already thinking of another visit.

Cottage in Bellport

What guests are saying

Waterfront Sunset Beach Cottage Oasis 1HR NYC

4.68 out of 5 average rating, 19 reviews3 months ago

This tiny, cozy space was exactly what we needed for an overnight place to relax and sleep, with a kitchen for us to make our coffee in the morning. We also felt we would have been quite comfortable there if we had needed to stay for a few days. The host was kind, responsive, friendly, respectful, and genuine. We will definitely stay here again. And the view! Gorgeous.

Cottage in Northport