Cottage vacation rentals in Oyster Bay

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Top-rated cottage rentals in Oyster Bay

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Guest favorite

A cozy living area showcases a dark sectional sofa, complemented by decorative pillows. Natural light filters through two windows with simple curtains. A wooden barn door adds charm, leading to a workspace furnished with a wooden desk and chair.

Cottage in Greenwood Lake

4.93 out of 5 average rating, 189 reviews

Cozy home in the Village of Greenwood Lake

Adorable country retreat under an hour from NYC - perfect for a romantic couples getaway or a family of 4. Located in the village, our quaint cottage is walkable to everything; Restaurants, bars, grocer, cvs, bagels, bus stop and even the public beach!! Minutes away from TONS of local attractions; drive-in, skiing, renaissance fair, wineries, shopping, lake activities, orchards, creameries, parks, Appalachian trail, spa, rafting, golf, water park, & so much more. Pets welcome! Permit #21-07603

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Cottage in Greenwood Lake

4.84 out of 5 average rating, 211 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

Just a little more than an hour away from NYC and a 4-min drive to the lake, this pet-friendly private retreat offers a hot tub, family room, spacious yard with fire pit, and a deck with a grill and comfy seating. The renovated interior has all the comforts of home including a full kitchen & streaming capabilities. Incredible perks include complimentary lake access at nearby beach, family board games, children's books, toys & a mini game table for ping-pong, air hockey, football & billiards!

Guest favorite

A long wooden boardwalk winds gently towards the horizon, flanked by a railing that provides a clear view of the serene beach and distant island. The bright blue sky, dotted with wispy clouds, enhances the coastal atmosphere of the setting.

Cottage in Milford

4.95 out of 5 average rating, 104 reviews

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Classic 1920s beach cottage perfect for your summer at the shore! It is tucked away on a quiet street, across from Silver Sands Beach Milford. This cozy cottage offers 2 bedrooms with bonus loft sleeping area. In one of CT's most desired shoreline locations, steps to the private beach & Silver Sands State Park boardwalk, walnut beach, ice cream and cafe. Close to downtown green which offers bars and restaurants, train to NYC and New Haven, Yacht Clubs and Yale. Beach Vacation. Pet Friendly!

Top guest favorite

A circular fire pit is surrounded by several wooden chairs arranged for seating. The fire pit is filled with black stones, with flames gently rising from its center. Lush greenery and a glimpse of the lake can be seen in the background.

Cottage in South Salem

5 out of 5 average rating, 109 reviews

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

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

4.97 out of 5 average rating, 143 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

Top guest favorite

Cottage in Guilford

4.99 out of 5 average rating, 103 reviews

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Guest favorite

The kitchen features modern stainless steel appliances, including a gas stove and dishwasher. Natural light fills the space through a window above the sink. White cabinetry and a light countertop contrast with warm wooden flooring, creating a bright and functional cooking area.

Cottage in Milford

4.95 out of 5 average rating, 326 reviews

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

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

A bright dining area is showcased with large windows allowing natural light to fill the space. A wooden table with ample seating is positioned in the center, surrounded by chairs. A modern light fixture hangs above, complementing the warm wooden floors.

Cottage in Fairfield Beach

4.98 out of 5 average rating, 121 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.

Guest favorite

A spacious waterfront deck features several seating options including two adirondack chairs and a dining table with chairs. A large umbrella provides shade. The calm waters of the lake reflect the surrounding green hills under a cloudy sky.

Cottage in Sterling Forest

4.92 out of 5 average rating, 117 reviews

Oasis on the water 1 hour from NYC

We could all use a little therapy: LAKE THERAPY that is! There is nothing like water to heal what ails you. This entirely renovated cottage sits right on the water. Window views will have you believing you are living on a houseboat. Morning Coffee or evening cocktails on the deck are the perfect way to begin and end the day. The area is full of amazing things to do (guest book provided) Come for the weekend or stay the week. You will never want to leave!!

Guest favorite

Cottage in South Salem

4.95 out of 5 average rating, 238 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 compact kitchenette is visible, featuring a microwave, sink, and a small shelf with dishware. Below is a black cart with a coffee maker. A colorful Matisse poster adorns the wall, adding an artistic touch to the space while a door leads to another area.

Cottage in Centerport

4.93 out of 5 average rating, 133 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

Cottage in Patchogue

4.94 out of 5 average rating, 239 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.