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!
Fully renovated/Walk to water & shops/fenced yard!
*Feb and Mar available for longer stays!Inquire!* *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 speed
Cozy Private Studio | Easy Transit & Beaches
Cozy private studio in a quiet residential neighborhood in Stratford, CT. Bright, clean, and thoughtfully prepared basement space with fast WiFi, self check-in, coffee, and hotel-style amenities. Designed to help you feel at home for short getaways, work trips, or extended stays. 1 minute to I-95, 5 minutes to Metro-North (40-minute ride to NYC). Close to beaches and nearby towns. Free, easy street parking. Privacy always respected. Convenient to Yale, Fairfield, and many other nearby colleges.
Walk to Wildemere Beach/ Pet Friendly Coastal stay
-A brief walk to Wildemere (3 minutes) or Walnut Beach (10 minutes) to enjoy the sun and water. -7 minute walk to the new Tyde at Walnut Beach!!! This peaceful beach community is welcoming and ready for you to explore. Take a stroll to the coffee shop, restaurants, beach boardwalk, and the BEST ice cream shop-Walnut Beach Creamery. Maybe cook or order in to relax on the beautiful patio by the fire pit while the kids have s’mores! -quick drive to famous pizza and hiking and farms -train to NYC
3BR Modern Beach Cottage | Walk to Beach & Tyde
Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom ( King, Queen+ Twin), 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, our modern farmhouse-style home features a full kitchen, a private backyard with a fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and end the day by the fire. Comfort, style, and location — all in one unforgettable stay!
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 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!
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
Summer 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.
Westshore Luxury
Relax in the cozy living spaces, unwind in the bonus room, or take a peaceful stroll along the sandy beach just steps from your door. Enjoy breathtaking sunrises and sunsets over the water, fall asleep to the soothing sound of waves, or explore the scenic shoreline by bike. Whether you’re visiting for a quiet weekend escape or a longer stay, this charming beach home offers the perfect balance of comfort and tranquility. Quiet home for rest and relaxation — no parties or events.
Bright, Stylish & Cozy Suite
Welcome to your calm and peaceful retreat — a bright, stylish, and cozy 3rd-floor walk-up suite designed for comfort and relaxation. Enjoy a sunny bedroom filled with natural light and beautiful views that make every morning special. This private space offers a quiet escape from the city buzz, blending modern style with a warm, homey feel. Perfect for those who appreciate calm surroundings, soft sunlight, and a touch of elegance in every corner.
Popular amenities for Stratford vacation rentals
Other great vacation rentals in Stratford
Guest favorite - ALL YEAR LONG!
Renovated House Steps Away From The Ocean
Private 1-Bdrm Apt in West Haven
Coastal Retreat • 5 min to Beach • 3BR
The Rose
Lux Modern Loft ,Ricport Studio 1 Peaceful Stay
Seaside Studio in Historic Bridgeport Brownstone
Salt & Blue | Walk to Beach & Tyde •4BR• Fire Pit
When is the best time to visit Stratford?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,188 GYD | G$30,979 GYD | G$31,188 GYD | G$36,212 GYD | G$45,003 GYD | G$51,283 GYD | G$54,632 GYD | G$54,004 GYD | G$44,375 GYD | G$41,654 GYD | G$40,608 GYD | G$40,817 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
What are the best places to stay in Stratford?
Stratford has accommodations in areas near the waterfront and around downtown, with options ranging from family-friendly homes to pet-welcoming stays. Neighborhoods close to parks and beaches are frequently suggested for convenient access to local attractions.
What are the best things to do in Stratford with kids?
Families frequently explore playgrounds and picnics at Boothe Memorial Park, enjoy sand and water play at Short Beach, or spend time at Stratford’s public parks. Seasonal nature programs are commonly attended by children.
What are some of the best things to do in Stratford?
Explore Roosevelt Forest for nature walks, visit the Stratford Historical Society for local heritage, and enjoy relaxing time at Short Beach. Area theaters and community events offer opportunities to connect with Stratford’s creative scene.
How is the weather in Stratford?
Stratford experiences cold winters from 24–44°F (-4–7°C) with regular rainfall, and warmer summers with highs around 68–83°F (20–29°C). Spring and autumn feature mild temperatures and colorful scenery, especially near coastal areas.
When is the best time to visit Stratford?
Late spring through early fall is often recommended for milder weather between 52–83°F (11–29°C) and outdoor activities. Early autumn brings colorful foliage, while summer highlights coastal experiences and local festivals.
What are the best places to visit in Stratford?
Popular sites include Boothe Memorial Park, the Stratford Historical Society, and picturesque Short Beach. Roosevelt Forest is a favorite for hiking and nature discovery, while Stratford Point draws visitors for scenic waterfront views.
What are some hiking trails in Stratford?
Stratford has woodland trails at Roosevelt Forest that locals often frequent, and nature paths at Stratford Point attract visitors who enjoy scenic coastal views. Both spots are popular for relaxed walks and birdwatching.
What are some family activities we can do in Stratford?
Visit Boothe Memorial Park for historic buildings and gardens, join recreational programs at local community centers, or spend a day picnicking and playing at Short Beach. Stratford’s parks often have events and activities suitable for all ages.
What are some of the best day trip ideas from Stratford?
Explore nearby towns along the Connecticut coastline, visit local museums or aquariums, and discover nature preserves just outside Stratford. Art galleries and state parks around the region are often recommended for day excursions.
Are there any pet friendly accommodations available in Stratford?
Stratford has pet-friendly vacation rentals, especially near Roosevelt Forest and waterfront areas. Many hosts allow dogs, and nearby parks are welcoming for walks and play.
What are some local tips for visiting Stratford?
Explore local parks, stroll historic neighborhoods, and enjoy Stratford’s coastal attractions. Many visitors find comfortable walking shoes useful, and locals suggest checking community event calendars for seasonal happenings.
What is Stratford known for?
Stratford is known for its coastal scenery, rich aviation history, and community events. The town has parks, historic sites, and theaters reflecting its cultural roots.
What are the best hidden gems to explore in Stratford?
Many enjoy finding quiet trails within Roosevelt Forest or admiring the historic architecture at Boothe Memorial Park. The Audubon Center provides peaceful birdwatching spots that are less frequented.
What are the best foods to try in Stratford?
Stratford has locally rooted seafood, including clam chowder and lobster rolls, as well as pizza and Italian specialties. Bakeries and cafes around downtown are known for fresh pastries and coffee.
What should I bring for a trip to Stratford?
Bring layers, as temperatures can shift throughout the day and seasons. Waterproof jackets are helpful in rainy months, and a camera is great for capturing scenic spots around the parks and beach areas.
What is the nightlife in Stratford like?
Stratford’s nightlife centers around casual bars, local eateries, and small venues with live music or trivia nights. Many locals gather for relaxed evenings in downtown spots or along the waterfront.
What are the most popular events or festivals in Stratford?
Seasonal festivals in Stratford include arts and crafts fairs, summer concerts near Short Beach, and celebrations around Labor Day weekend. Community theater productions and holiday events at Boothe Memorial Park draw visitors and locals alike.
Are there family friendly vacation rentals in Stratford?
You can find family friendly rentals in neighborhoods close to Boothe Memorial Park, Short Beach, and local playgrounds. Options range from cozy homes to larger spaces suitable for groups or families.
Quick stats about vacation rentals in Stratford
Total vacation rentals
Explore 180 vacation rentals in Stratford
Nightly prices starting at
Stratford vacation rentals start at G$6,280 GYD per night before taxes and fees
Verified guest reviews
Over 6,170 verified reviews to help you choose
Family-friendly vacation rentals
120 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 70 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
4.9 Average rating
Stratford stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Rentals with pools Stratford
- Rentals with outdoor seating Stratford
- Rentals with beach access Stratford
- Rentals with a patio Stratford
- Family-friendly rentals Stratford
- Waterfront rentals Stratford
- Pet-friendly rentals Stratford
- Apartment rentals Stratford
- Rentals with a fire pit Stratford
- House rentals Stratford
- Beachfront rentals Stratford
- Rentals with a fireplace Stratford
- Rentals with a washer and dryer Stratford
- Fitness-friendly rentals Stratford
- Yale University
- Yankee Stadium
- Jones Beach
- Citi Field
- Cooper's Beach, Southampton
- Astoria Park
- Thunder Ridge Ski Area
- Fairfield Beach
- USTA Billie Jean King National Tennis Center
- Southampton Beach
- Bronx Zoo
- Robert Moses State Park Beach
- Sunken Meadow State Park
- Mohawk Mountain Ski Area
- Jones Beach State Park
- Hammonasset Beach State Park
- Bear Mountain State Park
- Kent Falls State Park
- UBS Arena
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Long Island Aquarium
- Yale University Art Gallery
- Ski Sundown