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
The kitchen features modern appliances set against white cabinetry, complemented by black bar stools. An outdoor gathering area showcases a circular fire pit surrounded by black Adirondack chairs, with waterfront views in the background. A cozy bedroom displays a large bed with decorative pillows and natural light filtering through the window.
Home in Stratford
5 out of 5 average rating, 17 reviews

Cozy Winter Escape • Firepit • Near Train & I-95

*Inquiries welcome | longer stays 🍁 *Beautiful 3BR, 2BA home on the Housatonic River *Balcony w/ stunning water views * SHARED AMENITIES : driveway, yard, shed *Historic neighborhood near I-95 & Metro-North Railroad *20 min to Yale, UB, Fairfield U, & SHU *Near hospitals: Yale, BPT, ST. V’s *Perfect for groups & families * 1 hr to NYC *5 min drive to the beach *10 min drive to Hartford Healthcare Amphitheater & Webster Bank Arena *Lots of local breweries and restaurants to explore.

Top guest favorite
A spacious back deck is displayed, featuring a dining set with an umbrella and additional seating. A small pergola is visible, offering shade. The exterior of the house shows a light-colored siding with several windows, seamlessly blending with the surrounding greenery.
Home in Stratford
5 out of 5 average rating, 47 reviews

Charming Folk Victorian Home

This spacious and beautiful Folk Victorian style farmhouse was built in 1917. This home has been updated to include all the modern-day necessities but still has all the charm of a 100 plus year old home! This home is truly the best of the best when it comes to location on the Golden Coast. Whether you are here to visit Fairfield County, New Haven County, or even NYC, you will find this home is close to everything! We are minutes from I-95, Route 15, Route 8, and Metro North Train Station!

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
4.93 out of 5 average rating, 169 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
4.96 out of 5 average rating, 252 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!

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, 150 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 studio features a neatly arranged sleeping area with a quilted bedspread in blue and white patterns. A desk with a chair is positioned nearby, allowing for a focused workspace. Natural light streams through sheer curtains, creating a bright and welcoming ambiance.
Home in Bridgeport
4.93 out of 5 average rating, 58 reviews

Cozy Studio in Bridgeport

Charming and fully equipped studio located in the heart of Bridgeport. Perfect for business travelers, couples, or solo adventurers, this cozy retreat features a comfortable bed, high-speed Wi-Fi, a private entrance, and a fully stocked kitchen for your convenience. Enjoy easy access to local restaurants, cafes, and shops, as well as public transportation and major highways. Whether you’re here for work or leisure, this studio offers everything you need for a relaxing and stress-free stay

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, 119 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.

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, 365 reviews

Fall 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
Home in West Haven
5 out of 5 average rating, 27 reviews

Private 1-Bdrm Apt in West Haven

House is located in quiet neighborhood and centrally located to just about everything you may need.... beaches, restaurants, entertainment, hospitals, colleges, shops via vehicle. Based on your interest and needs in restaurants, food, shops, activities, etc, you can use Google Maps, Yelp, Uber Eats, etc to provide you with several options. Nicely setup one full-sized bed apartment that sleeps two, provides you with privacy and comfort.

Guest favorite
A well-lit entryway is shown, featuring a door that leads outside. The open layout displays a small dining table with chairs nearby and a glimpse of a kitchen area at the left. The floor is finished with light-colored tiles while the walls are painted white.
Condo in Stratford
4.94 out of 5 average rating, 47 reviews

Comfortable apartment near all communal facilities

I have an apartment located in an excellent quiet area with easy access. It is furnished and is very close to different areas such as supermarkets, restaurants, hospitals and universities. It also has 100% filtered water to drink. Something very important is that NO type of drugs are accepted, NO Viper or electronic cigarettes or Hookah are NOT accepted on this property. If we find odors or drug residues, they will be reported and fined.

Top guest favorite
A bright and modern kitchen area features white cabinetry and stainless steel appliances. A large island is equipped with seating for three, while a cozy living space with two leather chairs is visible in the background. Natural light filters through multiple windows.
Apartment in Prospect Hill
5 out of 5 average rating, 171 reviews

The Winchester House at Science Park-Yale

Located 2 blocks from Yale University's Franklin and Murray College and Ingall's Ice rink, The Winchester House at Science Park is a newly renovated luxuriously appointed 2 bedroom 2.5 bathroom apartment. The apartment features bespoke amenities, free secure off-street parking, snacks and beverages, stylish furniture, 1000 ct. beddings, ample cooking pantry items and everything you need as a guest. Let us welcome you in relaxed luxury!

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, 162 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.

Popular amenities for Stratford vacation rentals

When is the best time to visit Stratford?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$32,629 GYDG$30,747 GYDG$31,374 GYDG$36,185 GYDG$44,970 GYDG$51,245 GYDG$54,591 GYDG$53,964 GYDG$44,342 GYDG$38,904 GYDG$36,394 GYDG$36,603 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 220 vacation rentals in East End, over 220 vacation rentals in Stratford Center Historic District, and over 220 vacation rentals in Lordship.

  • 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 House Rentals in Stratford?

    Enhance your stay in our House Rentals with the most popular amenities: over 120 homes with air conditioning, over 130 homes with wifi, over 120 homes with a kitchen, over 110 homes with free parking, 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 100 vacation rentals in Stratford featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do cottage rentals in Stratford have a kitchen?

    Absolutely! We offer over 10 cottage 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 house rentals in Stratford have wifi?

    Absolutely! We offer over 130 house 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 60 vacation rentals for guests traveling with pets.

Quick stats about vacation rentals in Stratford

  • Total vacation rentals

    Explore 190 vacation rentals in Stratford

  • Nightly prices starting at

    Stratford vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,230 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

    110 properties have a dedicated workspace

  • Wi-Fi availability

    180 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!