Waterfront vacation rentals in Old Saybrook

4.97 out of 5 average rating, 221 reviews

A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.

Home in Niantic

Beachfront Paradise

Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

4.93 out of 5 average rating, 332 reviews

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

4.87 out of 5 average rating, 219 reviews

A riverfront deck is furnished with two lounge chairs and a glass table, surrounded by lush greenery and trees. The view overlooks a calm stretch of the Patchogue River, creating a serene environment for relaxation and enjoyment of nature.

Cottage in Westbrook

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

4.99 out of 5 average rating, 945 reviews

The exterior view features a small wooden cabin surrounded by vibrant green trees. A stone path leads to a seating area, comprising four metal chairs and a table. Inside, the cozy octagonal space is lit by natural light filtering through several windows, showcasing a full-sized bed adorned with a colorful patterned quilt.

Tiny home in Norwich

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

4.91 out of 5 average rating, 106 reviews

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

4.94 out of 5 average rating, 333 reviews

A glass desk is positioned beside large windows, offering views of the water and sky. A cozy chair with a fluffy seat cover complements the desk. A stack of books, binoculars, and a soft-lit lamp are arranged on the desk, enhancing the workspace atmosphere.

Apartment in Stonington

Mystical Ocean View in Historic Stonington Borough

Enjoy stunning ocean views of Stonington Harbor and Fishers Island Sound from multiple floors of this spacious, comfortable apartment for 6. Located in historic Stonington Borough, Connecticut's oldest village, you can relax in the private library, then explore this picturesque area with acclaimed restaurants, shops, and museums all within walking distance. And with Downtown Mystic, I-95, and RI's beaches just a short drive away, you can have it all, located half way between Boston and NYC!

4.89 out of 5 average rating, 255 reviews

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!

Come relax at this cute and cozy cottage overhanging a large and beautiful lake! Whether it's a family trip, a couple's getaway, or a best friends reunion, this place has something for everyone. From relaxing on the deck with a beautiful view, to kayaking and canoeing, or swimming in the summer, there is much fun and peaceful relaxation to do at the cottage. Also, it's just a 10 minute drive to Mystic, wineries, orchards, the shoreline, restaurants, and 5 minutes to Foxwoods casino.

4.97 out of 5 average rating, 222 reviews

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

4.99 out of 5 average rating, 157 reviews

A welcoming view of Belle Vue Cottage features a well-kept lawn with a sign indicating its name. The cottage is framed by trees, with a driveway leading to it. A garage is visible in the background, contributing to the serene atmosphere of the neighborhood.

Cottage in Old Saybrook

Belle Vue Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

4.95 out of 5 average rating, 173 reviews

Home in Centerport

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

4.92 out of 5 average rating, 296 reviews

The interior space showcases exposed wooden beams and a bright, open layout. A comfortable seating area is positioned near large windows that provide natural light and views of the surrounding trees. A round dining table is visible, accompanied by a set of stylish chairs.

Home in Cornwall

Tucked-away Charming Forest Cabin w/ Private Brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin

4.93 out of 5 average rating, 138 reviews

Home in Clinton

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: July 2026 - Jan 2027 = All Open Availability SUMMER 2026: July + Aug + Sept Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Popular amenities for Old Saybrook waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.96 out of 5 average rating, 103 reviews

The spacious attic living area features a combination of cozy seating options, including a leather couch, two upholstered chairs, and a coffee table with decorative lanterns. Natural light filters in through the windows, illuminating the warm hues of the decor. A dining table is visible in the background.

Apartment in Mystic

"Meteor": River View Penthouse in Downtown Mystic

4.83 out of 5 average rating, 237 reviews

A wooden dock extends into the water, lined with boats gently bobbing on the surface. Lush green hills rise in the background, while a clear blue sky with scattered clouds frames the scene. People are gathered along the dock, enjoying the views.

Apartment in Northport

Harbor Studio - Across from historic Northport doc

4.99 out of 5 average rating, 114 reviews

A cozy outdoor fire pit area features four Adirondack chairs gathered around a warm fire. Soft lighting from string lights above enhances the tranquil setting, with natural greenery surrounding the space. Guests are seen enjoying conversation, adding to the inviting atmosphere.

Apartment in Chester

The Millhouse Downtown Chester

4.94 out of 5 average rating, 161 reviews

Apartment in Middlebury

Cozy Apartment with Water View of Brook

4.84 out of 5 average rating, 193 reviews

Two paddleboats are moored next to a wooden dock, resting on calm waters. The boats feature a blue color with a simple design, and the dock extends towards the lake, reflecting the peaceful setting.

Apartment in Middletown

Lakeside apartment 2.5 miles from Wesleyan campus!

4.88 out of 5 average rating, 495 reviews

Two Adirondack chairs are positioned by the water's edge, reflecting soft lights from distant boats on a calm evening. The still water mirrors the warm glow, creating a tranquil atmosphere. Nearby, a small fire pit adds warmth to the outdoor space, surrounded by lush greenery.

Apartment in New Haven

Fair Haven Heights Entire 1 Bedroom Apartment

4.8 out of 5 average rating, 444 reviews

A spacious deck is shown, offering a clear view of the Thames River and surrounding waterfront. Two light-colored lounge chairs are positioned on the deck. A series of docks and distant boats are visible on the water, with a backdrop of a partly cloudy sky.

Apartment in New London

Large Waterfront Luxury Apartment

4.97 out of 5 average rating, 177 reviews

A bright sleeping area features a spacious bed with light-colored bedding, positioned beside large windows dressed with gray curtains. A minimalist TV stand holds a television, with a colorful wall art piece providing a vibrant accent against the neutral walls.

Apartment in Groton

Beautiful studio overlooking the Mystic River

Waterfront house rentals

4.96 out of 5 average rating, 138 reviews

Home in Waterford

Coastal New England Waterfront Home-The Reed House

4.92 out of 5 average rating, 158 reviews

A charming white house with a welcoming porch is framed by a well-maintained garden. Pathways of stone lead to the entrance, surrounded by vibrant shrubs and flowers. The clear blue sky adds brightness to the serene setting.

Home in Groton

1 Bedroom Suite in the Heart of Mystic

4.92 out of 5 average rating, 181 reviews

A charming stone exterior is visible, featuring a private entrance with a sliding glass door. The path is made of stone, surrounded by a well-maintained lawn. In the background, sitting areas and greenery are discernible, enhancing a serene outdoor experience.

Home in Clinton

Amazing 2BR Riverfront Gem

4.99 out of 5 average rating, 164 reviews

The exterior of a lakefront cottage is illuminated by warm lighting at dusk. The structure features a vaulted roof with large windows, surrounded by trees. A deck extends around the cottage, reflecting on the calm water, creating a serene and inviting atmosphere.

Home in Coventry

Cozy cottage 5 minutes from UConn

4.94 out of 5 average rating, 177 reviews

An open-concept living area showcases a modern kitchen with stainless steel appliances and a granite island with stool seating. A spacious dining table is set nearby, complemented by a comfortable seating area with a sectional couch. Natural light filters through the large windows.

Home in Salem

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

4.95 out of 5 average rating, 258 reviews

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

Home in Springs

Private beach, fully updated house, on 2 acres.

4.94 out of 5 average rating, 34 reviews

A two-story waterfront home is set against a serene evening sky, featuring a spacious front lawn. Large windows invite natural light, while a balcony provides an upper-level retreat. A stone patio with seating is visible, enhancing outdoor relaxation options.

Home in Old Saybrook

Red Bird Waterfront Home. Dock available extra!

5 out of 5 average rating, 110 reviews

The cottage features a welcoming exterior with a front porch and an American flag displayed. Lush landscaping with green grass and carefully arranged plants surrounds the gravel pathway leading up to the entrance, illuminated by soft evening light.

Home in East Greenwich

Luxury Cottage on the Potowomut River 2bd/2b

Waterfront condo rentals

4.92 out of 5 average rating, 36 reviews

Condo in Montauk

Sun N Sound Resort, Montauk, NY

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

4.86 out of 5 average rating, 130 reviews

Beautiful condo on Long Islands Northfork

5 out of 5 average rating, 256 reviews

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

Condo in Montauk

Montauk Waterfront Condo w/ Sunset Views

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

4.9 out of 5 average rating, 185 reviews

Beautiful Waterview Condo on the North Fork of LI

4.78 out of 5 average rating, 37 reviews

A sunlit corner of the room features a tall plant stand made of natural materials, adorned with various plants. Sheer curtains are gracefully draped over a glass door, leading to a balcony overlooking a pool area, creating an open and airy feel.

Condo in Montauk

Condo on the ocean in Montauk

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

4.88 out of 5 average rating, 162 reviews

Waterfront Escape | Private Beach, Pool & Views

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

4.9 out of 5 average rating, 154 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport