House holiday rentals in Madison

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.

4.93 out of 5 average rating, 142 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

Stay with us for a relaxing, family lake vacation! Bring your family to our peaceful, private and BRAND NEW 3 bedroom - 2-bathroom home. We are located one block from the Gardner Lake public boat launch, easy access to the public beach. Just a short drive to Mystic, Stonington, Vineyards, Mohegan Sun & Foxwoods. Close to CT College, Mitchell, and USCGA. Cook your favorite meal in our fully equipped kitchen, you will think you never left home! Contact Peter or Adam to discuss your situation.

4.93 out of 5 average rating, 103 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

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

4.96 out of 5 average rating, 247 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

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 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.

5 out of 5 average rating, 197 reviews

An open-concept living space is illuminated by natural light, featuring a modern kitchen with a large marble island and bar seating. A cozy seating area is positioned nearby, with a view of a decorative sign reading 'Relax.' A spiral staircase leads to the upper loft.

Home in Preston

Lake Home w/Game Room 5 Min To Foxwoods & Mohegan

Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 5 min. from Foxwoods, 10 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

4.98 out of 5 average rating, 195 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!

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, 209 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.

4.99 out of 5 average rating, 139 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

Popular amenities for house rentals in Madison

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 195 reviews

The exterior of a Cape Cod style beach house is captured at sunset, showcasing a spacious upper balcony with an umbrella and illuminated railings. The warm hues of the sky enhance the inviting atmosphere of the home, while surrounding trees add to the serene setting.

Home in New London

Sunset Oasis 1 @ Ocean Beach: $1Mil View 6 Queen

4.88 out of 5 average rating, 124 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, 118 reviews

Home in Stonington

Lux 4BR Private Indoor Heated Pool - Mystic Home

Superhost

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.

Home in Milford

4.83 out of 5 average rating, 106 reviews

Spacious 4 bedroom, oasis with ocean views galore

4.98 out of 5 average rating, 182 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

4.86 out of 5 average rating, 275 reviews

An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.

Home in The Hamptons

Exclusive Sag Harbor Compound

4.93 out of 5 average rating, 159 reviews

A swimming pool with clear blue water is surrounded by a spacious deck. Lounge chairs with striped cushions are arranged for relaxation. Colorful umbrellas provide shade over outdoor sofas, and lush greenery in the background enhances the serene environment.

Home in The Hamptons

Large heated pool, games room, near private beach

4.96 out of 5 average rating, 169 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

Weekly house rentals

5 out of 5 average rating, 11 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

The exterior of the newly renovated home is shown, featuring a modern gray facade with multiple windows. Pathway lighting adds a warm touch as twilight sets in, illuminating the neatly landscaped yard and highlighting the inviting entrance.

5 out of 5 average rating, 16 reviews

Whispering Meadow House

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

5 out of 5 average rating, 9 reviews

The exterior of a cottage is displayed, featuring a warm orange front door framed by a simple porch with steps leading up. The building's shingles are a natural brown, complemented by multiple windows that invite daylight. Lush greenery surrounds the entrance, enhancing the welcoming appearance.

Home in Branford

5 Star Branford Cozy Cottage

5 out of 5 average rating, 25 reviews

The estate is set on expansive green lawns, framed by mature trees. The picturesque house features a charming combination of traditional architecture and modern details, with expansive verandas and a large outdoor deck providing ample space for relaxation.

Home in East Haddam

Elegant Countryside Estate

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.

5 out of 5 average rating, 24 reviews

Coast and Country Private Estate

5 out of 5 average rating, 37 reviews

A comfortable living area features a gray sofa positioned around a low coffee table. A television rests on a media console against the wall, with natural light streaming through two windows that overlook greenery outside.

Home in Higganum

The Doll House

5 out of 5 average rating, 42 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

Private house rentals

4.9 out of 5 average rating, 31 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

4.98 out of 5 average rating, 47 reviews

An aerial view captures the expansive sandy beach stretching along the coastline, adjacent to serene waters reflecting sunlight. Houses line the shore, with some beach chairs positioned near the water's edge, creating a peaceful coastal scene.

Home in Westbrook

Barnacle Bay Beach House

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!

4.73 out of 5 average rating, 240 reviews

A charming entrance is framed by an archway adorned with decorative ironwork. The door, painted in a soft turquoise, is complemented by a welcoming wreath. Lush green foliage surrounds the entryway, creating a serene outdoor environment.

Home in Old Saybrook

The Cottage

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!

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.

4.92 out of 5 average rating, 59 reviews

Guilford cozy in-law apt with private entrance

4.86 out of 5 average rating, 86 reviews

A modern design villa is situated on a lush hillside, surrounded by greenery. The structure features clean lines and large windows, blending with the natural landscape. In the background, the Connecticut River glimmers under the sunlight, adding to the serene atmosphere.

Home in Deep River

Starship River Views: Dates Just Newly Released

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.