House holiday rentals in Madison

5 out of 5 average rating, 124 reviews

Jan/Feb longer stays avail! Inquire! New Firepit!

*Jan and Feb 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

5 out of 5 average rating, 155 reviews

Home in North Haven

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

4.93 out of 5 average rating, 258 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.

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, 248 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!

4.94 out of 5 average rating, 124 reviews

A tranquil outdoor scene features a lush green lawn surrounding a calm pond. The reflection of trees and the nearby home can be seen in the water. A picnic table sits on the grass, inviting relaxation amidst the natural surroundings.

Home in Southington

Connecticut Chalet: Experience Fall in New England

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.

4.99 out of 5 average rating, 143 reviews

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

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, 168 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway with an amazing river view, peaceful neighborhood, and in the heart of fall foliage and holiday scenes. 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, and lots more.

4.98 out of 5 average rating, 201 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 Branford

“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.

4.99 out of 5 average rating, 141 reviews

An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.

Home in Haddam

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

4.94 out of 5 average rating, 121 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 Branford

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

A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.

4.96 out of 5 average rating, 120 reviews

Oceanfront Retreat with 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.

Popular amenities for house rentals in Madison

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.88 out of 5 average rating, 125 reviews

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

Home in The Hamptons

4 BD w/ Heated Pool in E Hampton, Fully Furnished

4.99 out of 5 average rating, 119 reviews

Home in Stonington

FREE Private Indoor Heated Pool - Mystic Home

A serene view of the Long Island Sound is captured at sunset, featuring soft pastel hues in the sky. A few clouds are present, and the gentle water surface reflects the vibrant colors. A flagpole with an American flag stands prominently in the foreground.

4.83 out of 5 average rating, 108 reviews

Spacious 4 bedroom, oasis with ocean views galore

4.98 out of 5 average rating, 183 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

4.91 out of 5 average rating, 104 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in North Fork

Modern farmhouse w/ pool, beach, horses and winery

4.96 out of 5 average rating, 170 reviews

The game room features vibrant lighting and a chalkboard wall that displays 'Casino Stay & Play House.' A foosball table is positioned alongside arcade machines, with several stools lined up against a bar counter. The floor is finished in light wood, enhancing the dynamic atmosphere.

Home in Montville

Casino Stay & Play House w/Hot Tub, Game Room

4.9 out of 5 average rating, 119 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

4.97 out of 5 average rating, 152 reviews

An expansive aerial view reveals a private pool surrounded by lush green grass and trees. A small pond is visible nearby, with vibrant foliage framing the scene. Open fields stretch into the distance, highlighting the rural setting on the property.

Home in Windham

mid century ranch style house on farmland

Weekly house rentals

4.91 out of 5 average rating, 33 reviews

A charming two-story farmhouse is depicted with a white exterior and a brown-shingled roof. The front porch is furnished with two chairs and includes a decorative lantern. Lush green grass surrounds the house, providing a serene setting amidst the trees.

Home in North Branford

The Gait House at High Gait Farm

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 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!

5 out of 5 average rating, 59 reviews

A spacious living area is presented, featuring a light-colored sectional sofa paired with a round coffee table. A dining table with six chairs occupies one corner. Large windows allow natural light to fill the room, with light curtains softly framing the views outside.

Home in Guilford

Coastal Farmhouse walking distance to town

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

4.94 out of 5 average rating, 31 reviews

A charming waterfront home showcases a well-maintained exterior featuring a spacious patio area with seating. Lush greenery surrounds the space, complemented by a stone pathway that leads to the entrance. The sky is bright and clear, enhancing the welcoming atmosphere of this retreat.

Home in Saybrook Manor

Red Bird Waterfront Home. Dock available extra!

4.92 out of 5 average rating, 59 reviews

An open-concept living area showcases a blend of comfortable seating and a cozy dining space. A well-defined sleeping area features a charming metallic bed, wooden furniture, and natural light filtering through a large arched window. Warm tones create an inviting and relaxed ambiance.

Home in Guilford

Guilford cozy in-law apt with private entrance

5 out of 5 average rating, 24 reviews

A modern home is showcased with a stone foundation and large windows, allowing natural light to fill the space. A spacious deck is visible, featuring colorful seating options and a stone wall that surrounds a well-maintained lawn, complemented by leafy trees.

Home in Guilford

Coast and Country Private Estate

Private house rentals

4.9 out of 5 average rating, 39 reviews

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

Home in North Fork

Waterfront NoFo Cottage w/ public beach access

4.82 out of 5 average rating, 38 reviews

A wooden deck features comfortable seating with white cushions, positioned around a small table set with tea and pastries. Lush green grass surrounds the area, dotted with tall trees, while a clear view of the harbor can be seen in the background.

Home in The Hamptons

Historic East Hampton Home - Private Beach Access

Superhost

Home in The Hamptons

5 out of 5 average rating, 3 reviews

Light-filled Retreat by the Bay

5 out of 5 average rating, 18 reviews

The exterior of Summersalt features a welcoming entryway with a bright pink door and decorative shutters. Vibrant hydrangeas frame the entrance, contributing to the home's charming coastal aesthetic. A covered porch provides shelter, inviting guests to step inside.

Home in Madison

New England shoreline charm, private beach access

4.84 out of 5 average rating, 80 reviews

A shingle style home is showcased, featuring a distinctive chimney. The exterior is finished with light-colored shingles, complemented by greenery surrounding the base. Tall trees can be seen in the background under a partly cloudy sky.

Home in Short Beach

Beautiful 3 bedroom shoreline house

A modern kitchen features a white island with a marble countertop and a sink, surrounded by cabinetry. The space is accented by pendant lighting over the island and a mix of stainless steel appliances. A full-length mirror and a hallway leading to additional areas are visible.

4.89 out of 5 average rating, 18 reviews

Remodeled Cottage in a Marina!

5 out of 5 average rating, 43 reviews

The house features a modern black exterior with large windows that welcome natural light. A set of wooden steps lead to the main entrance, flanked by a deck that extends toward the surrounding landscape. A detached garage is visible in the background.

Home in East Hampton

CT River Retreat - Modern Home with CT River Views