House holiday rentals in Madison

5 out of 5 average rating, 134 reviews

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

*Feb and Mar available for longer stays!Inquire!* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speed

4.93 out of 5 average rating, 303 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.

4.95 out of 5 average rating, 22 reviews

A charming cottage is set amidst lush greenery and colorful hydrangeas. The front porch is adorned with rocking chairs, inviting relaxation. A red door adds a vibrant contrast to the light exterior, while gravel pathways guide the way through the well-kept yard.

Home in Madison

Perfect Cape Beach Cottage in Madison CT!

Come enjoy your perfectly quintessential New England vacation in this beautiful beach cottage in Madison, Conncecticut - modern, luxe, and pull-at-your-heart-strings-endearing, your worries will melt away in this peaceful property. DEEDED BEACH ACCESS TO PRIVATE NEIGHBORHOOD SANDY BEACH - pics of the beach included. Note that bedrooms are located at the top of a (one-story) spiral staircase - if anyone in your party has mobility issues or questions on access, please contact host for inputs.

4.98 out of 5 average rating, 119 reviews

The exterior of a two-story lakeside home is framed by lush greenery and colorful flower beds. A stone path leads to the water's edge, where a wooden dock and steps offer direct access. The inviting porch features large windows and a deck, perfect for outdoor gatherings.

Home in East Hampton

Classic Lakehouse~Fire Pit_Canoes_Kayaks & Sunsets

Private lakefront home on Lake Pocotopaug with a fishing dock, kayaks, fire pit, and spectacular sunset views — perfect for family & friend getaways. Welcome to Lakeside Ferns, where you’ll enjoy direct waterfront access and private dock for swimming, fishing, kayaking, canoeing, and boating. Grill dinner, relax in the hammock by the water, and gather around the outdoor fire pit for s’mores under the stars. End each day with breathtaking sunsets over the lake — beautiful in every season.

A scenic waterfront terrace is framed by natural rock formations and lush greenery. An umbrella provides shade over a seating area featuring two Adirondack chairs and a small table, all offering unobstructed views of the water and boats in the distance.

5 out of 5 average rating, 29 reviews

Mulberry Seaside Cottage

Enjoy direct water views any time of year in this cozy cottage. Relax on the generous porch swing, eat dinner overlooking the water, watch the sunset on the secret waterfront terrace, and stay active kayaking, biking, and swimming. The large backyard is great for yard games. In the cooler months, cozy up to the outdoor gas fire or inside with a book while watching a stunning winter sunset over the water. Minutes to the charming Guilford green, restaurants, Yale University and train station.

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.

4.96 out of 5 average rating, 257 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

4.98 out of 5 average rating, 226 reviews

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Indian Neck

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

4.97 out of 5 average rating, 209 reviews

Home

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, 177 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.

4.94 out of 5 average rating, 128 reviews

A comfortable living area features a light-colored sofa accompanied by two lamps on side tables. A textured area rug lies beneath a coffee table, while natural light filters through multiple windows, creating a bright and open space. A dining area is visible in the background.

Home in Indian Neck

Charming home, easy access to everything Branford

Full home, comfortable and very well equipped. Private fenced in backyard with patio dining area. Off-street (driveway) parking. Short Walk to the Shoreline Greenway trail. Less than a mile to downtown, parks, beaches, restaurants, marina, Stoney Creek Brewery. Near event venues, The Owenego and Pine Orchard club. Close to New Haven. Family(kid) Friendly home with private fenced in backyard with patio dining area. Equipped with Pack N Play, highchair, booster seat, etc

4.96 out of 5 average rating, 135 reviews

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Superhost

4.93 out of 5 average rating, 136 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: May 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

Popular amenities for house rentals in Madison

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 306 reviews

The large two-tiered deck is illuminated with soft lighting, creating a cozy atmosphere. A staircase leads to the upper level, where seating and decor are visible. An above-ground pool is situated beside the deck, surrounded by greenery and evening skies.

Home in Montville

Casino Wine Down House with Winter Igloo

4.97 out of 5 average rating, 212 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

4.91 out of 5 average rating, 112 reviews

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

Breathtaking home with unforgettable views & pool!

4.92 out of 5 average rating, 127 reviews

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

Home in Springs

Private & Pristine with Pool and Kid’s Playard

4.98 out of 5 average rating, 107 reviews

A spacious living area features large windows that provide natural light and views of the surrounding trees. Comfortable leather furniture includes a sofa and an armchair, arranged around a rustic coffee table on a textured area rug. A potted plant adds a touch of greenery.

Home in Litchfield

Hilltop House/HOST &Co.

4.96 out of 5 average rating, 106 reviews

Home in North Fork

Stunning Farmhouse in NoFo I Heated Pool, Wineries

4.91 out of 5 average rating, 224 reviews

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

4.97 out of 5 average rating, 185 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

Weekly house rentals

A spacious lawn leads to a charming beachfront cottage, surrounded by lush greenery and large boulders. The structure features multiple windows and a sunroom, blending with the natural setting. A deck area is visible, inviting outdoor relaxation and enjoyment of the peaceful surroundings.

4.95 out of 5 average rating, 78 reviews

Scenic Mulberry Point Connecticut Beach House

5 out of 5 average rating, 23 reviews

A collage showcases the various entertainment and relaxation areas. The top left features a game room with arcade machines and a dartboard. The top right highlights a manicured putting green. The bottom left displays the exterior of the home with outdoor seating, while the bottom right depicts a home gym with workout equipment against a bright orange wall.

Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green

4.95 out of 5 average rating, 74 reviews

The image presents a serene beach scene, featuring a sandy pathway leading to a calm water body. A safety barrier is visible in the water, marking designated swimming areas. Lush green grass borders the beach, enhancing the tranquil coastal environment.

Home in Westbrook

Zion's Light Beach Cottage

4.9 out of 5 average rating, 10 reviews

Coastal Getaway on Marsh Near Beach, Town, Trails

A charming single-story home is surrounded by landscaped greenery, featuring tall hedges and flowering shrubs. The front entrance is framed by a set of stairs leading to a white door with side windows. A paved walkway guides visitors to the front of the house, offering a welcoming view.

5 out of 5 average rating, 12 reviews

South Beach Oasis

The exterior of the home is framed by a lush green lawn and landscaped flower beds. A charming facade with multiple gabled roofs and window arrangements can be seen. The surrounding trees add a natural touch to the peaceful setting.

5 out of 5 average rating, 36 reviews

Entire home - Cheerful 4 bedroom on the shoreline.

A small, charming home is shown from the exterior, featuring light grey siding and a sloped roof. Framed by trees, the property includes a welcoming porch with several windows and a chimney. A green lawn surrounds the house, complemented by tidy shrubs.

4.94 out of 5 average rating, 50 reviews

Tiny home one block from the town green.

4.97 out of 5 average rating, 70 reviews

The inviting entrance of the cottage is shown, featuring a front porch and path bordered by lush greenery. Vibrant flowers add color to the landscape, while a warm glow emanates from the entryway, highlighted by the soft evening sky.

Home in Westbrook

Sea Salt Air Changes Everything

Private house rentals

A view of the exterior of the blue house, showcasing a white lattice railing along the patio. Steps lead down to the water, with a calm blue surface reflecting the sky. Potted plants add a touch of greenery to the space.

5 out of 5 average rating, 36 reviews

Charming 2BR Beach House, Overlooking the Water

5 out of 5 average rating, 16 reviews

An aerial view of Quarry House showcases its Mid-Century Modern design surrounded by lush trees. The expansive wraparound deck with seating provides a space for relaxation, while the home's large windows reflect the evening light, seamlessly blending indoor and outdoor living.

Home in Haddam

Quarry House: Mid-Century Modern

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, 80 reviews

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

5 out of 5 average rating, 15 reviews

An American flag is displayed prominently in the foreground, with the sun setting over the water in the background. The sky is painted with soft hues as the sun begins to dip beneath the horizon, illuminating the shoreline and creating a serene coastal scene.

Home in Old Saybrook

Waterfront Oasis 4Bdr/2b

5 out of 5 average rating, 17 reviews

A bright living room features large windows that overlook a serene view of the pond. Comfortable gray sofas and two navy blue chairs with yellow accents are arranged around a glass coffee table on a patterned area rug. A stone fireplace adds a cozy touch to the space.

Home in Essex

4 Bedrooms Modern Home with Water View & Access

A sunroom features a large wooden table surrounded by six black wicker chairs. Floor-to-ceiling glass windows offer views of the lush greenery outside. A comfortable lounge chair is positioned to one side, enhancing the relaxed atmosphere.

4.8 out of 5 average rating, 81 reviews

Summer is filling up-Beach, Shopping and Golf

5 out of 5 average rating, 8 reviews

The exterior of a waterfront cottage showcases a blend of natural wood shingles and modern roofing. Multiple large windows provide abundant light, and a patio area is situated in front. The property is surrounded by lush greenery and offers views of the nearby water.

Home in Indian Neck

Waterfront Cottage in Branford

A bright living area features large glass doors that open to a beautiful view of the ocean. Comfortable seating includes a sectional sofa and accent chairs, with a modern TV and light wood flooring adding to the ambiance. An umbrella provides shade for outdoor seating on the deck.