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Vacation rentals in Stratford

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Top-rated vacation rentals in Stratford

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

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Top guest favorite
Apartment in Milford
4.95 out of 5 average rating, 205 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 favorite
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, 623 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 favorite
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, 175 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 favorite
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
4.97 out of 5 average rating, 258 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 favorite
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, 171 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 favorite
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
4.94 out of 5 average rating, 387 reviews

Spring Sale! CozyCottage/Pet-friendly/ WalktoBeach

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.

Top guest favorite
A cozy living room is featured with a combination of a grey sofa and an orange couch. A decorative white coffee table rests on a patterned area rug, while a faux fireplace is accented by a round sunburst mirror and decorative items. Natural light enters through a nearby window.
Cottage in Milford
4.99 out of 5 average rating, 162 reviews

3BD Cottage | Walk 2 Beach and Tyde | Fire pit

Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom, 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, our modern farmhouse-style home features a full kitchen, a private backyard with a fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and end the day by the fire. Comfort, style, and location — all in one unforgettable stay!

Guest favorite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 435 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Top guest favorite
Home in Milford
4.96 out of 5 average rating, 138 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.

Top guest favorite
The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.
Apartment in Fairfield
4.98 out of 5 average rating, 172 reviews

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Guest favorite
A private hot tub is situated beneath a covered patio, surrounded by blooming azaleas. The inclined garden path leads to a charming wooden house featuring a slate roof, with warm sunlight illuminating the scene. Outdoor seating is available nearby.
Home in Stratford
4.96 out of 5 average rating, 223 reviews

Cozy Colonial - Private Hot Tub & Entire House

The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.

Top guest favorite
Home in Fairfield
4.96 out of 5 average rating, 207 reviews

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities for an unforgettable stay.

Popular amenities for Stratford vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Stratford

Bungalow in Trumbull
4.83 out of 5 average rating, 253 reviews

Cozy, romantic cabin by the lake.

Guest favorite
A bright sleeping area features a spacious bed adorned with various pillows in shades of gray and white. Two table lamps flank the bed, providing soft illumination. The warm wall color enhances the cozy ambiance of the room.
Apartment in Trumbull
4.93 out of 5 average rating, 70 reviews

Cozy studio unit

Guest favorite
A sandy beach is depicted with a wooden walkway leading towards the shoreline. An umbrella provides shade for beachgoers, while gentle waves are visible in the distance. A pier extends into the water, contributing to the serene coastal setting.
Home in Milford
4.94 out of 5 average rating, 63 reviews

Adorable Walnut Beach Cottage.

Top guest favorite
Apartment in Fairfield
5 out of 5 average rating, 74 reviews

Modern Studio Near Fairfield & Sacred Heart Univ

Top guest favorite
Home in Milford
4.95 out of 5 average rating, 42 reviews

Modern Beach Mood 2!

Guest favorite
A serene bedroom is highlighted by a spacious bed with white linens. A colorful stained glass window casts vibrant hues across the room. A small plant sits on the windowsill, and a soft light fixture provides gentle illumination from a corner.
Apartment in Bridgeport
4.83 out of 5 average rating, 29 reviews

Lux Modern Loft ,Ricport Studio 1 Peaceful Stay

A cozy living room features a comfortable sofa adorned with decorative pillows, a wooden rocking chair, and a coffee table with a bowl. A wooden entertainment unit holds a television, while wooden flooring leads to a staircase and an adjoining room filled with natural light.
Home in Milford
4.85 out of 5 average rating, 116 reviews

Cozy Colonial Style House in Beach Town

Guest favorite
A covered deck area features a wooden storage bench, providing a functional seating option. The view shows a quiet street alongside the property, with houses and vehicles visible in the background. Railings frame the space, enhancing the outdoor experience.
Apartment in Milford
4.96 out of 5 average rating, 23 reviews

Silver Sands Suite

When is the best time to visit Stratford?

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Frequently Asked Questions

  • What are the best places to stay in Stratford?

    Stratford has accommodations in areas near the waterfront and around downtown, with options ranging from family-friendly homes to pet-welcoming stays. Neighborhoods close to parks and beaches are frequently suggested for convenient access to local attractions.

  • What are some of the best things to do in Stratford?

    Explore Roosevelt Forest for nature walks, visit the Stratford Historical Society for local heritage, and enjoy relaxing time at Short Beach. Area theaters and community events offer opportunities to connect with Stratford’s creative scene.

  • How is the weather in Stratford?

    Stratford experiences cold winters from 24–44°F (-4–7°C) with regular rainfall, and warmer summers with highs around 68–83°F (20–29°C). Spring and autumn feature mild temperatures and colorful scenery, especially near coastal areas.

  • When is the best time to visit Stratford?

    Late spring through early fall is often recommended for milder weather between 52–83°F (11–29°C) and outdoor activities. Early autumn brings colorful foliage, while summer highlights coastal experiences and local festivals.

  • What are the best places to visit in Stratford?

    Popular sites include Boothe Memorial Park, the Stratford Historical Society, and picturesque Short Beach. Roosevelt Forest is a favorite for hiking and nature discovery, while Stratford Point draws visitors for scenic waterfront views.

  • What are some family activities we can do in Stratford?

    Visit Boothe Memorial Park for historic buildings and gardens, join recreational programs at local community centers, or spend a day picnicking and playing at Short Beach. Stratford’s parks often have events and activities suitable for all ages.

  • What are some of the best day trip ideas from Stratford?

    Explore nearby towns along the Connecticut coastline, visit local museums or aquariums, and discover nature preserves just outside Stratford. Art galleries and state parks around the region are often recommended for day excursions.

  • Are there any pet friendly accommodations available in Stratford?

    Stratford has pet-friendly vacation rentals, especially near Roosevelt Forest and waterfront areas. Many hosts allow dogs, and nearby parks are welcoming for walks and play.

  • What are some local tips for visiting Stratford?

    Explore local parks, stroll historic neighborhoods, and enjoy Stratford’s coastal attractions. Many visitors find comfortable walking shoes useful, and locals suggest checking community event calendars for seasonal happenings.

  • What is Stratford known for?

    Stratford is known for its coastal scenery, rich aviation history, and community events. The town has parks, historic sites, and theaters reflecting its cultural roots.

  • What are the best hidden gems to explore in Stratford?

    Many enjoy finding quiet trails within Roosevelt Forest or admiring the historic architecture at Boothe Memorial Park. The Audubon Center provides peaceful birdwatching spots that are less frequented.

  • What are the best foods to try in Stratford?

    Stratford has locally rooted seafood, including clam chowder and lobster rolls, as well as pizza and Italian specialties. Bakeries and cafes around downtown are known for fresh pastries and coffee.

  • What should I bring for a trip to Stratford?

    Bring layers, as temperatures can shift throughout the day and seasons. Waterproof jackets are helpful in rainy months, and a camera is great for capturing scenic spots around the parks and beach areas.

  • What is the nightlife in Stratford like?

    Stratford’s nightlife centers around casual bars, local eateries, and small venues with live music or trivia nights. Many locals gather for relaxed evenings in downtown spots or along the waterfront.

  • What are the most popular events or festivals in Stratford?

    Seasonal festivals in Stratford include arts and crafts fairs, summer concerts near Short Beach, and celebrations around Labor Day weekend. Community theater productions and holiday events at Boothe Memorial Park draw visitors and locals alike.

  • Are there family friendly vacation rentals in Stratford?

    You can find family friendly rentals in neighborhoods close to Boothe Memorial Park, Short Beach, and local playgrounds. Options range from cozy homes to larger spaces suitable for groups or families.

  • How much does it cost to stay in apartment rentals in Stratford?

    Experience the best of Stratford with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Stratford?

    Yes! Work meets play with ease at over 100 vacation rentals in Stratford featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about vacation rentals in Stratford

  • Total vacation rentals

    Explore 180 vacation rentals in Stratford

  • Nightly prices starting at

    Stratford vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 6,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Stratford vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Stratford rentals

  • 4.9 Average rating

    Stratford stays are highly rated by guests—averaging 4.9 out of 5!

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