Holiday rentals in Stratford

4.95 out of 5 average rating, 161 reviews

Flat in Milford

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!

4.94 out of 5 average rating, 144 reviews

Loft in Milford

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.

4.99 out of 5 average rating, 112 reviews

Home in Milford

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

4.89 out of 5 average rating, 102 reviews

Flat in South End

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.

4.97 out of 5 average rating, 143 reviews

Cottage in Weston

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

4.95 out of 5 average rating, 324 reviews

Cottage in Milford

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly

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.

5 out of 5 average rating, 26 reviews

Apartment in Stratford

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.

4.98 out of 5 average rating, 129 reviews

Flat in Fairfield

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.

4.94 out of 5 average rating, 178 reviews

Home in Stratford

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.

4.95 out of 5 average rating, 91 reviews

Flat in Bridgeport

Stylish Sheek Loft Ricport Studio 2, Downtown

Please note location and area before booking!!! (DONT BOOK if you don’t know it’s loud and busy) Conveniently located Downtown Bridgeport. Feel free to light a fire🔥. Unique hand tinted windows provides the space with an open feel although it is a small space. Queen size bed, fireplace, and aesthetics sets this apartment apart from any rental you can find. *pet fee for pets. Please let me know in advance.

4.9 out of 5 average rating, 50 reviews

Home in Bridgeport

Lavish retreat near downtown

Kick back and relax in this home away from home. Motion sensored lights with spacious waterfall shower unit and outdoor space for dinning and lounge. Full kitchen with multiple tv units(Netflix, Hbo,Hulu, paramount & Starz) and rest areas. Coffee and tea available. 5 mins away from downtown , accessible to trains & bus. Parking available in backyard of property . ( 1 Queen bed, 1 Sofa bed)

5 out of 5 average rating, 8 reviews

Home in Lordship

Akasa Ocean Front Oasis- Seasonal Pool, Grill

Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or requests. The total price you see includes your savings, so you can book with confidence. Discounts may display differently across booking platforms, but rest assured, they’re built into your final price.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Stratford holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Stratford

5 out of 5 average rating, 8 reviews

Quiet, cozy Stratford location

KaitlynRating, 5 stars1 week ago

If you’re staying in or near Stratford, I would suggest staying here! The space is great for two people, and would be comfortable for longer stays. It was also spotlessly clean, smelled phenomenal, and felt super cozy. 10/10, would HIGHLY recommend.

5 out of 5 average rating, 15 reviews

Cece's Nature Lover Resort

ChaseRating, 5 stars3 days ago

Daniela was so warm and welcoming and treated me like family when I was there! She and Mike were always up for a chat and were genuinely interested in getting to know me which was nice. They were also very gracious in the use of their home and full access to appliances in the kitchen so I could cook meals. I wish I could have stayed longer!

4.94 out of 5 average rating, 32 reviews

Elegant & Cozy Sunlit Room

KathleenRating, 5 stars2 weeks ago

Great place with good lighting in the bedroom! Host was very kind and proactive.

Private room in New Haven

4.89 out of 5 average rating, 27 reviews

Aesthetic Room 6 Min From Yale

GeraldineRating, 5 stars1 month ago

Daiana was incredibly helpful and accommodating with all my questions. The apartment is lovely, with a wonderfully powerful shower! The neighbourhood is very residential with no nearby shops or restaurants. But if you are going to an event at the Yale Bowl or nearby sports area (which I was), it is very convenient. And it is less than 10 minutes by car or Uber from downtown New Haven. Daiana's beautiful apartment and very friendly attitude made my stay memorable. Highly recommended!

Private room in Bridgeport

5 out of 5 average rating, 13 reviews

Bright Room in the Lake House!

LuisRating, 5 stars3 weeks ago

Mara was a great host, we felt very welcome in her home. We would love to come back the next time we’re in the area.

Superhost

5 out of 5 average rating, 8 reviews

lakeside single private bedroom

NadineRating, 5 stars2 weeks ago

very down to earth and proactive host, respectful of your space and belongings and is also really flexible.

4.86 out of 5 average rating, 92 reviews

Individual Room in Stratford

JamesRating, 5 stars7 months ago

I had a wonderful stay. The description was accurate, and the host was excellent. Thank you!