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Holiday houses in Stratford

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Stratford

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.95 out of 5 average rating, 188 reviews

The Boathouse, private downtown Harborside suite

The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

Top Guest favourite
A spacious living area features a dark sofa and a patterned armchair, offering comfortable seating. A wooden Murphy bed is folded against the wall, while a small table with a lamp and decorative flowers adds to the inviting ambiance. Large windows provide natural light.
Guest suite in Fairfield
4.94 out of 5 average rating, 430 reviews

Private Studio Apartment; Kitchen; Fully Furnished

This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield U; an easy train ride to NYC. (Need the Murphy bed? PLEASE do not wait until just before checkin to let us know that!)

Top Guest favourite
An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.
Apartment in Milford
4.97 out of 5 average rating, 606 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Guest favourite
A spacious living area is illuminated by natural light streaming through large windows. A comfortable gray sofa with decorative pillows faces a modern coffee table. A stylish area rug adds color, while a wall-mounted TV and decorative plants enhance the space.
Apartment in New Haven
4.95 out of 5 average rating, 399 reviews

Luxury Apt with Parking and Gym | Downtown at Yale

Nestled in the heart of New Haven’s historic downtown, our designer home is part of the city’s most prestigious new luxury complex, renowned for its unmatched amenities and design. Highlights: • Prime location just steps from Yale University • Immaculately cleaned before every stay • Complimentary coffee, plush linens, and premium toiletries • 24/7 state-of-the-art fitness center • Expansive rooftop terrace with grills and chic lounges • Over 700 sqft of bright and sophisticated living space

Top Guest favourite
A serene waterfront view is presented, showcasing calm waters reflecting a soft pink sky. Lush green grasses frame the foreground, while a tree line marks the horizon, creating a tranquil landscape. A few ducks can be seen gently floating on the water.
Loft in Milford
4.94 out of 5 average rating, 164 reviews

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

Guest favourite
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
4.96 out of 5 average rating, 246 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!

Top Guest favourite
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.
Home in Milford
4.99 out of 5 average rating, 140 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

Guest favourite
The entrance features a charming porch framed by white railings, with potted plants adding greenery. A welcoming front door is accentuated by patriotic decorations, and a small seating area is visible beside lush greenery and a well-maintained lawn.
Home in Fairfield
4.9 out of 5 average rating, 124 reviews

Fairfield Entire Upstairs Suite / 2Rms + Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bathroom Exclusive Driveway Parking➕locked entrance leading airbnb, separate from full-time renters on 1st FL Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

Guest favourite
A cozy living area features a dark, comfortable couch and a decorative rug. A wall-mounted television is positioned above a simple mantel with a potted plant. Natural light filters through floral curtains, illuminating a wooden desk and chair against the wall.
Apartment in South End
4.89 out of 5 average rating, 113 reviews

Seaside Studio in Historic Bridgeport Brownstone

Keep it simple at this peaceful and centrally-located historic brownstone built by P.T. Barnum for his staff 140 years ago. Basement unit across the street from Bridgeport University, 1 block to Seaside Park and beaches, 5 min walk to amphitheater, and 10 min walk to Metro North or LI ferry. Includes kitchenette with fridge/freezer, microwave, stove and oven, desk, couch, wifi, tv with Roku , iron, hairdryer, and full bathroom. We are pet friendly up to 2 with additional $25 per pet.

Top Guest favourite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 181 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Top Guest favourite
Home in Milford
5 out of 5 average rating, 122 reviews

HGTV reno! Fall Foliage, near New Haven, Firepit!

*Inquire now monthly discount Jan* *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 speeds

Guest favourite
A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.
Cottage in Milford
4.95 out of 5 average rating, 352 reviews

Fall Sale! CozyCottage/Pet-friendly/Walk to Beach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Popular amenities for Stratford holiday rentals

When is the best time to visit Stratford?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$273 NZD$257 NZD$262 NZD$302 NZD$376 NZD$428 NZD$481 NZD$463 NZD$404 NZD$325 NZD$304 NZD$306 NZD
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Quick stats about holiday rentals in Stratford

  • Total holiday rentals

    Explore 170 holiday rentals in Stratford

  • Nightly prices starting at

    Stratford holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 5,880 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Stratford holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Stratford rentals

  • 4.8 Average rating

    Stratford stays are highly rated by guests—averaging 4.8 out of 5!