Vacation rentals with beach access in Madison

Vacation home in Guilford

A spacious deck features multiple blue Adirondack chairs, all facing the tranquil waters of Long Island Sound. The horizon showcases a gentle gradient of pastel colors, signaling the transition from day to evening, while the calm water reflects the serene atmosphere.

4.99 out of 5 average rating, 135 reviews

Spacious Oceanfront Getaway with Spectacular Views

Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)

4.94 out of 5 average rating, 296 reviews

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”.

A historic New England home features a classic white exterior with multiple windows. Surrounding greenery includes mature trees and a well-maintained lawn. The side of the house provides a glimpse of a separate structure, enhancing the spacious outdoor area.

4.97 out of 5 average rating, 212 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

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.

4.92 out of 5 average rating, 181 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Extremely comfortable house with amazing views in a peaceful neighborhood. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, music, and lots more.

4.93 out of 5 average rating, 136 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: June 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug 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

4.96 out of 5 average rating, 186 reviews

The exterior of the historic barn is featured, showcasing weathered wood siding and a welcoming entrance with double doors. The structure is surrounded by trees and a gravel pathway leading to the front door. Soft morning light highlights the natural beauty of the setting.

Barn in Essex

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

4.96 out of 5 average rating, 110 reviews

A spacious living area features a large sectional sofa adorned with red cushions, complemented by a coffee table and side tables. Bright light floods the room through the sliding glass doors, opening to the outdoor deck. A staircase leads to a lofted area, enhancing the open feel.

Apartment in Guilford

Cozy Private Lake Q Retreat

Escape to a charming lakeside haven! Our cozy 1-bed, 1-bath retreat is a tranquil getaway. Nestled by the water, it's perfect for a romantic escape or a solo recharge. Enjoy stunning lake views, a comfy bedroom, and a serene bathroom. Unwind on the private deck and explore nearby nature trails. A lofted office space with l-shaped desk invites both creativity and productivity. Your lakeside escape awaits! NO CLEANING FEE!

4.99 out of 5 average rating, 169 reviews

A bright and airy living area features large windows allowing natural light to filter in. A wooden coffee table displays various books, complemented by a bouquet of flowers. Seating includes a light-colored armchair and a sofa adorned with patterned cushions, while a dining area is visible in the background.

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

Ecape to the charming beach community of Indian Cove in Guilford and unwind in this beautifully renovated 1920s coastal cottage. Full of character and warmth, this spacious retreat blends historic charm with modern comfort-featuring wood floors, high beam ceilings, and a stunning stone fireplace that creates the perfect cozy atmosphere year round.

4.83 out of 5 average rating, 127 reviews

A vibrant blue entrance door is framed by neatly trimmed evergreen shrubs, with a welcome mat placed on stone steps leading to the inviting threshold of the home. A mailbox is positioned beside the door, adding to the entrance's charm.

Guesthouse in Guilford

The Little Blue Cottage

Relax at this unique and tranquil getaway. Enjoy the charm of an antique home while being in your own private space. Minutes from all conveniences and beaches. Walking distance to town. Grill and relax on the spacious back porch. or walk to the Mill Pond to picnic.

4.86 out of 5 average rating, 250 reviews

A wooden pathway leads through sandy terrain, flanked by low vegetation. The scene is set against a clear blue sky, creating a serene atmosphere that guides visitors toward the shoreline.

Home in Westbrook

Family-Friendly Cottage by The Shore

Welcome to our cottage in Westbrook, CT! A clean, comfortable and convenient spot to stay so you are free to explore and relax. Beautiful beaches, shopping and entertainment all around makes for the perfect spot.

4.95 out of 5 average rating, 359 reviews

Bungalow in Old Lyme

Pet Friendly Bungalow!!!

Fishing blackhall pond... ... kayaks.. canoe on premises...life jackets and paddles ...great setting.. sunsets...quiet... peaceful slice of heaven. No extra charge for the Bullfrog!!!

4.96 out of 5 average rating, 106 reviews

A clean and inviting living area features a light-colored sofa with decorative pillows, complemented by a wooden coffee table and a flat-screen television. Natural light filters through a window adorned with bamboo shades, and a wall clock adds a functional touch.

Barn in Guilford

Pristine Carriage House Apartment Downtown

Quaint, cozy, pristine carriage house apartment one block from our Historic Guilford Town Green, short walk to train station & marina.

Popular amenities for Madison beach access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.95 out of 5 average rating, 210 reviews

A spacious studio layout includes a cozy queen bed adorned with a geometric quilt. Nearby, a comfortable seating area features a patterned sofa and a green chair. Natural light flows through large windows adorned with bamboo shades, illuminating the warm wood floor.

Apartment in Milford

The Boathouse, private downtown Harborside suite

4.9 out of 5 average rating, 113 reviews

An expansive ocean view is showcased from the studio, featuring calm waters that reflect the sunlight. Soft waves gently lap at the sandy shore, while lush greenery lines the foreground, contrasting with the clear blue sky above.

Apartment in Montauk

Ocean View Studio with King Bed

4.91 out of 5 average rating, 587 reviews

A welcoming living space is shown, featuring a large flat-screen TV displaying a beach-themed greeting. A light wood dining table with chairs is set, accompanied by a fully equipped kitchen with wooden cabinets and modern appliances. Natural light filters in through the windows.

Apartment in West Haven

Cozy & Private Apartment Near the Ocean

4.98 out of 5 average rating, 144 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

4.88 out of 5 average rating, 130 reviews

Apartment in Montauk

Recharge at our Renovated ocean front unit

4.95 out of 5 average rating, 123 reviews

An open living area features a comfortable sectional sofa and a large area rug, with natural light streaming through multiple windows. A dining table is visible, accompanied by stools, and the kitchen area includes modern appliances and a view into the outdoor patio space.

Apartment in Montauk

Modern Montauk retreat with wood stove by Harbor

4.97 out of 5 average rating, 269 reviews

A serene view of Pattagansett Lake is presented, with gentle ripples reflecting the sky. Surrounding hills are adorned with trees displaying autumn colors, while fluffy clouds drift above. The calm waters enhance the tranquil atmosphere of the natural setting.

Apartment in East Lyme

Brand New Direct Lakefront - Panoramic Sunsets

4.97 out of 5 average rating, 174 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

House rentals with beach access

4.98 out of 5 average rating, 91 reviews

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Branford

Adorable Beach House on LI Sound

4.97 out of 5 average rating, 263 reviews

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

Designer Beach Retreat on Exclusive Cedar Beach

4.84 out of 5 average rating, 140 reviews

The living room features a modern design with a curved green and orange sofa surrounding a light wood coffee table. A striking black fireplace provides a focal point against a light wall. A statue and decorative elements contribute to the welcoming ambience.

Home in West Haven

Westshore Luxury

5 out of 5 average rating, 140 reviews

Home in Milford

Fully renovated/Walk to water & shops/fenced yard!

4.88 out of 5 average rating, 32 reviews

Home in Old Saybrook

White Bird Beachfront. Dock available extra.

A bright living area features large windows that overlook the ocean, allowing natural light to fill the space. The room is furnished with a blue sofa, two armchairs, and a coffee table. A small plant adds a touch of greenery, and a dining area is visible in the background.

5 out of 5 average rating, 37 reviews

Soundscape Beachfront House!

A warm bedroom features a red accent wall, complemented by a spacious bed adorned with floral-patterned bedding. Bedside tables with lamps are positioned on either side, and a piece of art hangs above. Natural light streams in through a window with light curtains.

4.95 out of 5 average rating, 82 reviews

“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach

5 out of 5 average rating, 24 reviews

An open-concept living area features a well-equipped kitchen with modern appliances and an island with seating. Neutral walls and wooden flooring create a warm ambiance. Two pendant lights hang above the kitchen island, illuminating the space and connecting seamlessly to the dining and living areas.

Home in Guilford

Coastal Getaway - walk to town and waterfront

Condo rentals with beach access

4.8 out of 5 average rating, 242 reviews

A view from the balcony overlooks the pool area, featuring a clear blue pool surrounded by lounge chairs. Colorful umbrellas provide shade for several tables, while the surrounding buildings reflect a simple, two-story design.

Condo in Montauk

Montauk Royal Atlantic Beach Resort North

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

4.85 out of 5 average rating, 162 reviews

Waterfront Escape | Private Beach, Pool & 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, 183 reviews

Beautiful Waterview Condo on the North Fork of LI

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.

4.89 out of 5 average rating, 150 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

5 out of 5 average rating, 4 reviews

Condo in Milford

Sunrise Retreat: Luxe Master Suite, Ocean Views!

4.8 out of 5 average rating, 66 reviews

A bright living room is showcased with wrap-around windows, offering panoramic views of the surrounding neighborhood. A modern coffee table sits at the center, accompanied by a comfortable couch. Natural light enters the space, creating a warm atmosphere, complemented by a potted plant.

Condo in Old Lyme

Forecastle at Soundview · Beach+OceanView+Sunrise

4.83 out of 5 average rating, 196 reviews

The studio features a queen-sized bed adorned with a floral-patterned blanket. A comfortable sofa and armchair are positioned nearby, along with a small table. Natural light filters through a nearby door, illuminating the warm wood flooring.

Condo in Montauk

Coastline View Studio

An expansive view of the ocean under a bright blue sky, featuring wispy clouds. The shoreline is lined with gentle waves, and a grassy area is visible in the foreground, leading down to the water.