
Vacation rentals in Stratford
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Stratford
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

Waterfront Beach Cottage in Connecticut
Our lovely cottage is as beautiful and peaceful as the photos. With gorgeous water views, it's a wonderful place to relax, walk on the beach, cook dinner and drink wine while watching the sun set. It's cozy and unforgettable, just 90 minutes from Grand Central on Metro North. First bedroom has a queen-size bed, and the second bedroom has a full-size bed. An extra-long twin in a quiet corner of the living area is both a daybed and extra accommodation. The bathroom has a shower and claw foot tub.

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!

Charming Riverview Home *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.

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.

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN
Classic 1920s beach cottage perfect for your summer at the shore! It is tucked away on a quiet street, across from Silver Sands Beach Milford. This cozy cottage offers 2 bedrooms with bonus loft sleeping area. In one of CT's most desired shoreline locations, steps to the private beach & Silver Sands State Park boardwalk, walnut beach, ice cream and cafe. Close to downtown green which offers bars and restaurants, train to NYC and New Haven, Yacht Clubs and Yale. Beach Vacation. Pet Friendly!

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!

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

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

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

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.

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.
Popular amenities for Stratford vacation rentals
Other great vacation rentals in Stratford

Quiet, cozy Stratford location

Tranquil Getaway : 1

Beautiful home

St Mary's by the Sea- in Black Rock

Private Room | Shared Comfort 2

LOVELY WELL APPOINTED ROOM - IN FAIRFIELD

Individual Room in Stratford

Modern Room 6 Minutes From Yale
Quick stats about vacation rentals in Stratford
Total rentals
170 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
5.9K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
10 properties have a pool
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.
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- Rentals with a fireplace Stratford
- Fitness-friendly rentals Stratford
- Rentals with a washer and dryer Stratford
- Rentals with outdoor seating Stratford
- Beachfront rentals Stratford
- Rentals with a patio Stratford
- Apartment rentals Stratford
- Waterfront rentals Stratford
- Rentals with beach access Stratford
- Rentals with pools Stratford
- Rentals with a fire pit Stratford
- House rentals Stratford
- Family-friendly rentals Stratford
- Pet-friendly rentals Stratford
- Yale University
- Jones Beach
- Yankee Stadium
- Citi Field
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- Gilgo Beach
- Robert Moses State Park
- Astoria Park
- Bronx Zoo
- Walnut Public Beach
- Thunder Ridge Ski Area
- Bethpage State Park
- Shinnecock Hills Golf Club
- Rye Playland Beach
- Rowayton Community Beach
- Cedar Beach
- Jones Beach State Park
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach