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Cottage holiday rentals in Long Island Sound

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Top-rated cottage rentals in Long Island Sound

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

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Guest favourite
A charming cottage with a red exterior is surrounded by a lush garden filled with various plants and flowers. A spacious covered porch extends across the front, offering a welcoming entryway. The well-manicured lawn is complemented by vibrant greenery and colorful blooms, creating a pleasant outdoor space.
Cottage in Mount Sinai

The Red Cottage Circa 1936

This cottage is a gem to be found! From the primary room to the charming loft, this cottage can sleep 6! There is a full working kitchen. For those who wish to do exploring, you will be centrally located on LI giving you great ease in using LI rail road (.5 mile) from cottage and Port Jeff Ferry (1mile)from cottage. There is a large fenced in yard with BBQ and outdoor seating if you wish to dine in. Dogs are allowed w/prior notice and a $65 pet fee per dog. You won’t beat this value reserve now.

4.8 out of 5 average rating, 552 reviews
Top Guest favourite
The sunroom features a light pink wall and a high ceiling with exposed beams. A comfortable wicker sofa with decorative throw pillows accompanies two matching chairs. A patterned area rug covers the floor, while a small table sits in the center. Soft light filters through sheer curtains.
Cottage in Guilford

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

4.94 out of 5 average rating, 307 reviews
Top Guest favourite
Cottage in Milford

3BR Cottage Walk to Beach and Tide Wedding Venue

Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom ( King, Queen+ Twin), 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!

4.99 out of 5 average rating, 178 reviews
Guest favourite
A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.
Cottage in Milford

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

4.88 out of 5 average rating, 109 reviews
Top Guest favourite
Cottage in Branford

Water Views & July 4 Fireworks – June 27, 2026

Quaint and romantic beachside retreat along the Connecticut shoreline, featuring spectacular waterfront views, breathtaking sunrises and July 4 Fireworks. Just 100 steps from the beach, with a cozy fire pit in the yard for relaxing evenings by the water. Enjoy swimming, kayaking, and other seaside activities, along with many exceptional local restaurants nearby. Conveniently located just 5 minutes from the Shore Line East train station and only a 10-minute drive or train ride to New Haven.

4.98 out of 5 average rating, 177 reviews
Top Guest favourite
A two-story beach cottage is presented with a light exterior and a spacious balcony. Large sliding glass doors are visible at the lower level, providing easy access to the outdoor space. Nearby, a driveway is seen leading towards the garage.
Cottage in Westbrook

A Beach House Gem

Beautiful beach cottage with a private beach. Sleeps up to 6 comfortably with two full beds and 1 queen in the master. with a beautiful balcony Full bath upstairs,1/2 off the kitchen entrance outside key on the key chain The main living area has a TV, air conditioning, and sliding doors to a deck. The updated kitchen has a dishwasher, microwave, cooktop, oven, and coffee maker. There are 2 parking spots in front of the garage The house is not winterized there are no bookings from Nov1

4.91 out of 5 average rating, 112 reviews
Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

4.97 out of 5 average rating, 392 reviews
Top Guest favourite
A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.
Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, 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. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

4.98 out of 5 average rating, 182 reviews
Superhost
Cottage in Branford

Cozy 2 Story Cottage in Short Beach Community

A cozy home in a beach community that has a central location with easy access to outdoor activities & local restaurants. The home is also 5 minutes from the Branford Train Station, Stony Creek Brewery, & Branford's town center. We are also a 10 minute drive from New Haven, home to Yale University, Yale Hospital and other colleges/universities. Our guests also gain access to Johnsons' Beach, a private residents only beach, located just around the corner from the home (3 minute walk)

4.85 out of 5 average rating, 268 reviews
Top Guest favourite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston

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

4.97 out of 5 average rating, 243 reviews
Guest favourite
A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.
Cottage in New Milford

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

4.94 out of 5 average rating, 252 reviews
Guest favourite
A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.
Cottage in Milford

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach

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.

4.94 out of 5 average rating, 417 reviews

Popular amenities for Long Island Sound cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Guest favourite
A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.
Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

4.95 out of 5 average rating, 210 reviews
Top Guest favourite
A jetted swim spa is positioned on a deck overlooking Lake Garda at sunset. The water's surface reflects soft hues of orange and pink, with serene trees framing the view. The spa displays an illuminated edge, enhancing the tranquil atmosphere of the lakeside setting.
Cottage in Burlington

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

4.98 out of 5 average rating, 192 reviews
Guest favourite
A wooden table set for dining overlooks a serene lake. Glassware and plates filled with food are arranged on the table, while white chairs offer seating. Lush greenery lines the shore, complementing the calm water and bright sky.
Cottage in Ledyard

Waterfront cottage overhanging the water!

4.89 out of 5 average rating, 257 reviews
Top Guest favourite
The inviting exterior of a cozy cabin is surrounded by lush greenery, with warm lights illuminating the covered porch. A fire pit is featured at the forefront, surrounded by four Adirondack chairs, creating a welcoming space for evening gatherings.
Cottage in Kerhonkson

Ye Little Wood | Cozy Forest Cottage with Hot Tub

5.0 out of 5 average rating, 250 reviews
Guest favourite
The charming cottage, with its white siding and red door accents, is set amidst lush greenery. A well-maintained yard features grass and flowering plants, while a stone wall frames the scene, adding to the property's rustic appeal.
Cottage in Litchfield

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

4.87 out of 5 average rating, 412 reviews
Top Guest favourite
The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.
Cottage in Bethlehem

Cozy Cottage |Quintessential CT | Pet Friendly

4.99 out of 5 average rating, 171 reviews
Top Guest favourite
A red wooden cottage is surrounded by lush greenery, featuring green window shutters and a covered porch. A wooden rocking chair is visible on the porch, inviting relaxation. The upper level includes a balcony that overlooks the picturesque landscape.
Cottage in Pine Bush

Catskills Cottage (w/ Hot Tub) on Top of the World

5.0 out of 5 average rating, 132 reviews
Top Guest favourite
A spacious outdoor deck is seen, featuring pink lounge chairs and a small black table with a decorative item. A shaded area with a red umbrella provides relief from the sun. Lush greenery and the tranquil lake are visible in the background under a clear blue sky.
Cottage in Greenwood Lake

Secluded Lakeview Escape with Hot Tub

4.98 out of 5 average rating, 152 reviews

Pet-friendly cottage rentals

Guest favourite
The image captures a serene beach scene at sunset, with soft colors reflecting on the calm water. Silhouetted figures are seen on the shore, engaged in various activities as the sun sets on the horizon, creating a peaceful atmosphere.
Cottage in Rocky Point

Adorable cottage

4.91 out of 5 average rating, 192 reviews
Top Guest favourite
Cottage in Hampton Bays

Hamptons Cottage.

4.93 out of 5 average rating, 123 reviews
Top Guest favourite
A portable cabana is placed on a sandy beach with a view of the ocean. Two blue beach chairs are positioned underneath the cabana, providing shade. The shoreline and gentle waves are visible in the background, framed by a clear blue sky.
Cottage in Amagansett

Amagansett Dunes Gem

4.94 out of 5 average rating, 111 reviews
Guest favourite
A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.
Cottage in Putnam Valley

Lakefront Cottage near Hudson Valley

4.88 out of 5 average rating, 329 reviews
Top Guest favourite
A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.
Cottage in Seymour

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

4.97 out of 5 average rating, 143 reviews
Guest favourite
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

Private cottage in horse country &1 hour from NYC!

4.95 out of 5 average rating, 278 reviews
Guest favourite
An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.
Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

4.95 out of 5 average rating, 135 reviews
Guest favourite
The living area features a vaulted ceiling with bright natural light streaming through large windows. A cozy seating arrangement includes a light grey couch and a comfortable chair. A stylized coffee table sits in the center, with a dining table set for two nearby.
Cottage in East Lyme

Your Nest Near The Beach

4.97 out of 5 average rating, 327 reviews

Private cottage rentals

Guest favourite
An open living space features wooden walls and bright hardwood floors. A cozy seating arrangement includes a sofa and a side table. A dining area with blue chairs is visible next to a large window, while a brick fireplace adds a rustic touch to the room.
Cottage in Southold

Cozy Cottage on the Great Pond near beach.

4.89 out of 5 average rating, 202 reviews
Top Guest favourite
The exterior of the cottage is characterized by a charming stone chimney and a vibrant green door. The white siding contrasts with lush greenery, while a small seating area features two colorful chairs on the well-maintained lawn. A stone pathway leads toward the entrance.
Cottage in East Haddam

Historic Hearthstone Cottage

5.0 out of 5 average rating, 111 reviews
Top Guest favourite
A tranquil lakeside scene at sunset features vibrant pink and orange hues reflected on the calm water. Silhouetted trees line the shore, and rolling mountains rise in the distance, creating a serene backdrop.
Cottage in South Salem

Serene lake front cottage 1 hour from NYC

4.97 out of 5 average rating, 148 reviews
Top Guest favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick

Ranch in the Woods | A Peaceful Designer Retreat

4.99 out of 5 average rating, 135 reviews
Guest favourite
A private deck overlooks a tranquil marsh, framed by vibrant flowers in terracotta pots. A shaded seating area includes a couch with cushions and a small table, inviting relaxation while enjoying the serene view of the water and surrounding natural greenery.
Cottage in Branford

Enchanted Cottage on the Marsh, walk to beach

4.97 out of 5 average rating, 136 reviews
Top Guest favourite
Cottage in South Salem

Oscaleta Guest House: Lakefront Cabin

5.0 out of 5 average rating, 139 reviews
Top Guest favourite
A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.
Cottage in Shelter Island

3 Bedroom Cottage Gem

4.97 out of 5 average rating, 129 reviews
Top Guest favourite
The living area features two comfortable sofas, a wooden coffee table, and a dining table set for four. A window allows natural light to fill the space, while decor accents create a relaxed environment. Air conditioning unit is visible on the wall.
Cottage in East Hampton

Carriage House - Cottage in East Hampton Village

4.98 out of 5 average rating, 382 reviews

Destinations to explore