House holiday rentals in Stratford

5 out of 5 average rating, 129 reviews

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

*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

A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.

4.96 out of 5 average rating, 337 reviews

Luxurious Barn With New England Charm

Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.

4.97 out of 5 average rating, 101 reviews

The kitchen features modern cabinetry with a contrasting dark granite island. Three cushioned stools are positioned at the island. Natural light enters through a window above the sink, illuminating new stainless steel appliances and a sleek backsplash. A door leads to the outdoor area.

Home in Black Rock

Cape on the Water

Welcome to our Cape on the Water! This unique property is located on beautiful Ash Creek, an inlet off Long Island Sound offering views of tidal wetlands, including tons of fish, bird, kayakers, paddle boarders, small sail boats etc. The house is a newly renovated Cape Cod with open floor concepts, updated Kitchen and bath rooms. Refinished oak hardwood floors through out the entire house. Brand new large deck. The house has a very cozy feel and has been also updated with brand new HVAC system.

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

4.98 out of 5 average rating, 138 reviews

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

A spacious backyard is visible, featuring well-maintained greenery and shading trees. A patio area made of paving stones extends towards the house, with a small table and grill positioned nearby. Bright sunlight filters through the surrounding foliage, creating a serene outdoor setting.

4.86 out of 5 average rating, 111 reviews

Bright 3-bedroom house with ample parking & patio!

Take in the sunshine at this peaceful & fully renovated Fairfield home! Private property in a gorgeous neighborhood, this house is a 10-min drive from Fairfield University & 7-min drive from Sacred Heart University. Right next to the Brooklawn Country Club. Central A/C, lots of natural light, large back patio & fire pit, washer/dryer, dishwasher, and strong Wi-Fi with Roku TV in both living room & family room. Public beach access available, highly-rated eateries, & tons of shopping nearby!

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, 148 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

4.97 out of 5 average rating, 143 reviews

Home in Wilton

The Cozy Little Cottage

Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

A bright living area features two plush sofas, one in a muted beige and the other in a deep blue, positioned around a circular wooden coffee table. Light-colored curtains adorned with a coral pattern frame the windows, while shelves on the walls display decorative items.

4.95 out of 5 average rating, 128 reviews

Families|Charming |King Bed| Near SHU

Welcome to our updated and inviting nautical-themed residence. The home is located close to the University of Bridgeport, Sacred Hearth University and St Vincents Hospital. Enjoy the excitement of the ambiance around the fire pit in the private backyard and a grill for cooking, and the convenience of all of the amenities in the home. Guests can truly relax and make the most of their time in our tranquil setting. There is a dedicated workspace for remote workers and is family friendly.

Two wicker chairs with patterned cushions are positioned beside a large window, offering a panoramic view of the sandy beach and ocean. The serene landscape includes gentle waves and distant beachgoers, framed by a bright sky.

4.99 out of 5 average rating, 146 reviews

Serene Waterfront Retreat - 400 ft Private Beach!

Welcome to a slice of waterfront heaven! Located on Milford's Cedar Beach, this newly renovated 3 bedroom / 1.5 bath home features over 400 feet of private beach. Enjoy breakfast prepared in the Chef's kitchen while watching one of the most radiant sunrises you will ever see. Stunning views from every room in the house. Wade into Long Island Sound with your own private beach. Located 3 doors down from the CT Audubon Society, known for its views & wildlife. We can't wait to host you!

5 out of 5 average rating, 105 reviews

A spacious living room features a large sectional couch adorned with colorful pillows, next to a smaller armchair. Natural light floods through wide windows framed by vibrant curtains. A wooden coffee table sits in the center, with art pieces displayed on the walls and a guitar nearby.

Home in Westville

Westville Schoolhouse by Stephanie and Damian

The beautiful "School House" sits in the heart of Westville, New Haven's most artsy and eclectic neighborhood. The "School House" is a 15 minute walk to the Westville Concert bowl, and the Yale Football stadium for an easy commute to a concert or game. Just a one minute walk to the center of Westville you will find Lotta's artist studio, Bella's restaurant, RAWA, Pistachio Coffee and Manjares Tapas & Wine, as well as the famous Camacho Garage restaurant amongst other attractions.

4.86 out of 5 average rating, 110 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

Relax in the cozy living spaces, unwind in the bonus room, or take a peaceful stroll along the sandy beach just steps from your door. Enjoy breathtaking sunrises and sunsets over the water, fall asleep to the soothing sound of waves, or explore the scenic shoreline by bike. Whether you’re visiting for a quiet weekend escape or a longer stay, this charming beach home offers the perfect balance of comfort and tranquility. Quiet home for rest and relaxation — no parties or events.

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.

4.95 out of 5 average rating, 127 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 Stratford

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 16 reviews

An inviting living area showcases a cozy green sofa and two light-colored armchairs, emphasizing a natural wood coffee table. A rustic stone fireplace adds warmth, with a well-equipped kitchen visible in the background, featuring a gray island with seating and stainless steel appliances.

Home in Brookfield

3.5 Acres of Relaxation, Pool, & Cozy Charm

5 out of 5 average rating, 17 reviews

Home in Weston

Dream Home w/ Pool & Basketball Court on 3 Acres

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.

4.82 out of 5 average rating, 112 reviews

Spacious 4 bedroom, oasis with ocean views galore

4.89 out of 5 average rating, 19 reviews

Home in Redding

Meeker Hill House - Country Escape w/ Heated Pool

4.8 out of 5 average rating, 30 reviews

A rustic cabin with a distinctive thatched roof is set among lush greenery. The natural stone steps lead to the entrance, and a wooden gate adorned with climbing vines is slightly ajar, inviting guests to explore the serene surroundings.

Home in Ridgefield

Log House, sits on 3acres. A retired mini farm.

4.9 out of 5 average rating, 121 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

Home in Norwalk

New place to stay

Casa la Secret 3 BDR 2 BTH HOUSE

A serene pool area is captured at sunset, featuring a tranquil water feature flowing into the pool. Surrounding trees are silhouetted against a sky painted in soft pink and purple hues, offering a peaceful evening atmosphere.

4.95 out of 5 average rating, 41 reviews

Renovated, Private, 4BR Cape w/Pool nr FFU/Town

Weekly house rentals

The exterior of a newly constructed home features a combination of blue and white siding. Large windows are present on multiple levels, allowing for ample natural light. A staircase leads to the entrance, while parking is available beneath the house.

4.84 out of 5 average rating, 64 reviews

Newly Built Beach House Getaway

A spacious living area features a gray sectional sofa with a light green throw draped over the arm. A large area rug in soft gray covers the hardwood floor, while natural light streams through multiple windows with blinds.

4.77 out of 5 average rating, 171 reviews

Golden Colonial Home

5 out of 5 average rating, 50 reviews

Walk to Beach-Pet Friendly-Fire Pit-Fenced Yard

A neatly arranged sleeping area features a spacious bed dressed in a bright blue quilt with decorative stitching. A nightstand with a lamp stands beside the bed, while light-colored walls and a door provide a sense of openness in the room.

4.85 out of 5 average rating, 27 reviews

Beautiful, Cozy basement space

A two-story building with gray siding and white trim is positioned on a quiet street. The structure features a wraparound porch and green door. The distance to the ocean is visible, with water beyond the nearby structures and a clear sky overhead.

4.9 out of 5 average rating, 80 reviews

Beach house - Sapphire Sandbar

The kitchen features white cabinetry with gold hardware and a black tile backsplash. A marble countertop holds a sink and a stove, while a microwave and various supplies are arranged above. Ample storage is provided, enhancing the functional design of the space.

4.89 out of 5 average rating, 72 reviews

Lavish retreat near downtown

5 out of 5 average rating, 36 reviews

The exterior of the modern beachside retreat is showcased, highlighting a three-story structure with balconies on the upper floors. The light-colored facade is complemented by stone accents and landscaped lawn, providing a welcoming entryway. Nearby streets and neighboring homes create a quaint coastal neighborhood ambiance.

Home in Fairfield Beach

Stareway to Heaven

4.94 out of 5 average rating, 34 reviews

The bedroom features a dark blue blanket draped over a spacious bed with a decorative pillow in vivid blue and white shades. Soft wall lamps illuminate the space beside matching bedside tables, while an elegant rose-patterned mural provides a serene backdrop.

Home in Stratford

The Rose

Private house rentals

4.97 out of 5 average rating, 70 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

A spacious living area features a comfortable blue sectional sofa and a dark coffee table. A television is mounted on the wall above a decorative media stand. In the adjacent dining area, a wooden table with several chairs is set on an area rug.

5 out of 5 average rating, 39 reviews

Walnut Beach's Hidden Gem

5 out of 5 average rating, 7 reviews

Home in Shelton

Shelton's New England Nest: 2 bed EV, Shower, W/D

The exterior of a charming beach house is presented, featuring a light-colored facade with a combination of siding and shingles. A welcoming front porch is visible, surrounded by a well-kept lawn and a walkable pathway leading to the entrance.

4.93 out of 5 average rating, 43 reviews

Cozy Milford Beach House

A charming two-story house is presented, featuring a welcoming front porch with white railings. The exterior is clad in beige siding, accented by large windows that let in natural light. Lush greenery is visible around the home, enhancing the overall curb appeal.

5 out of 5 average rating, 41 reviews

The Salty Porch

An open-concept area showcases a modern kitchen with an island and seating, complemented by sleek stainless steel appliances. The dining table features a decorative centerpiece, while a cozy living room area is visible through the doorway, highlighted by natural light from large windows.

5 out of 5 average rating, 13 reviews

Fairfield’s Four bedroom Family Home

A spacious outdoor deck is furnished with a large sectional seating area, featuring soft cushions for comfort. A glass-top coffee table is positioned at the center. The view includes a glimpse of the nearby beach and coastal structures.

4.94 out of 5 average rating, 80 reviews

Modern Beach Getaway

A comfortable living area features a plush sectional sofa with neutral cushions, arranged around a round wicker coffee table. Natural light fills the space, highlighting the light wood flooring and a serene coastal-themed artwork on the wall. Two stylish light fixtures add an elegant touch.