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
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!

Guest favorite
An open bedroom suite is featured, with a warm-colored comforter covering a spacious bed. A wooden dresser stands beside the bed, and a leather couch is positioned against the wall. Natural light enters through windows, brightening the neutral-toned walls.
Guest suite in Ansonia
4.74 out of 5 average rating, 519 reviews

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

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, 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!

Top 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, 163 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.

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, 139 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
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 favorite
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, 112 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 favorite
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 favorite
Home in Milford
5 out of 5 average rating, 121 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 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
4.95 out of 5 average rating, 350 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.

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
4.97 out of 5 average rating, 152 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
An open studio space is highlighted by original wooden beams and warm, polished hardwood floors. Multiple skylights provide ample natural light. Furnishings include a comfortable couch, a coffee table, and storage units adorned with artwork, creating a charming, functional atmosphere.
Place to stay in Southport
4.93 out of 5 average rating, 276 reviews

Sunny Westport Studio Apt. Above Historic Mill

Historic Charm Meets Modern Comfort: A Unique Studio Retreat Perched atop a restored 19th-century Cider Mill, this sunlit studio blends timeless character with modern amenities. Enjoy stunning views of a picturesque stream, serene meadows, and diverse wildlife. Just moments from Southport Village, yet offering a peaceful escape, it's perfect for history lovers, business travelers, and design enthusiasts seeking a unique getaway.

Popular amenities for Stratford vacation rentals

When is the best time to visit Stratford?

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Avg. priceG$32,653 GYDG$30,770 GYDG$31,397 GYDG$36,212 GYDG$45,003 GYDG$51,283 GYDG$57,562 GYDG$55,469 GYDG$48,352 GYDG$38,933 GYDG$36,421 GYDG$36,630 GYD
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Frequently Asked Questions

  • Where should I stay in Stratford?

    Make yourself at home in Stratford by choosing from our most frequently booked neighborhoods. We have over 210 vacation rentals in East End, over 210 vacation rentals in Lordship, and over 210 vacation rentals in Stratford Center Historic District.

  • Do cottage rentals in Stratford have air conditioning?

    Absolutely! We offer over 10 cottage rentals with air conditioning in Stratford. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Stratford?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Stratford have free parking?

    Absolutely! We offer over 110 house rentals with free parking in Stratford. Enjoy a tailored experience with all the comforts you desire.

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

    Yes! Work meets play with ease at over 90 vacation rentals in Stratford featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Stratford have a kitchen?

    Absolutely! We offer over 110 house rentals with a kitchen in Stratford. Enjoy a tailored experience with all the comforts you desire.

  • Are there Stratford vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Stratford, available on Airbnb. Make a splash and soak up the sun in style!

  • Do cottage rentals in Stratford have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Stratford. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Stratford?

    Stratford has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Stratford?

    Four-legged friends are welcome in Stratford. Choose from more than 70 vacation rentals for guests traveling with pets.

Quick stats about vacation rentals in Stratford

  • Total vacation rentals

    Explore 170 vacation rentals in Stratford

  • Nightly prices starting at

    Stratford vacation rentals start at G$6,279 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,880 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 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

  • 4.8 Average rating

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