Vacation rentals in Stratford

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Top-rated vacation rentals in Stratford

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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, 48 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
Apartment in Fairfield
5 out of 5 average rating, 64 reviews

New & Modern Studio Apartment in Fairfield CT

This newly reconstructed downstairs stylish, modern, and spacious studio features a queen bed & a queen pull-out sofabed with remote lighting, luxe bathroom with towels and refillables, a fully loaded sleek kitchen, a 70” TV with surround sound, and guest-controlled ambient lighting. Enjoy a private entrance, in-suite laundry, guest-controlled heat, and ceiling fan. Close to Fairfield & Sacred Heart Universities, shops, beach, and quick NYC transit. Comfort and convenience in one chic space!

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, 156 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
4.92 out of 5 average rating, 64 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 sleeping area features a spacious bed centered against a wooden wall unit with built-in shelves. Soft bed linens in muted colors are arranged neatly, with decorative pillows adding a touch of style. Nightstands on either side hold elegant lamps that softly illuminate the space.
Apartment in Edgewood
4.96 out of 5 average rating, 515 reviews

Urban Garden Suite

Relax & Recharge in Westville’s Hidden Gem in New Haven. Unwind in this serene, beautiful, cozy, spotless garden apartment tucked inside a historic three-family home in charming Westville. The cozy, open-concept design blends modern upgrades with warm, thoughtful touches, creating the perfect balance of comfort and style.🌿 Enjoy peaceful surroundings, inviting details, and everything you need for a seamless stay. Your attentive (yet discreet) hostess ensures you’ll feel truly at home.

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, 370 reviews

Winter 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, 29 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 cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.
Guesthouse in Westville
4.92 out of 5 average rating, 338 reviews

Square6ix Stylish Guesthouse in Westville

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

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, 48 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
An elegant Arts & Crafts bungalow showcases a blend of architectural styles under a clear blue sky. The inviting façade features a distinctive porch, a brick chimney, and a nearby garage. Lush gardens adorned with vibrant plants enhance the home’s outdoor appeal.
Guest suite in Wallingford
5 out of 5 average rating, 642 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

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, 164 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
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.

Popular amenities for Stratford vacation rentals

When is the best time to visit Stratford?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$32,586 GYDG$30,706 GYDG$31,333 GYDG$36,137 GYDG$44,911 GYDG$51,177 GYDG$54,519 GYDG$53,893 GYDG$44,284 GYDG$41,568 GYDG$40,524 GYDG$40,733 GYD
Avg. temp0°C1°C4°C10°C16°C21°C24°C24°C20°C14°C8°C3°C

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$2,089 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!