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Stratford, CT vacation rentals
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Best Vacation rentals and Airbnb offers in Stratford, CT

Best Stratford, CT vacation rentals with a balcony

Walnut Beach Luxury House - 6 Houses From Private Beach - Stratford, CT
Stratford, CT
12/25 – 12/31
$1025/nighttotal: $6150 (6 )

Walnut Beach Luxury House - 6 Houses From Private Beach

3 2
apartment , Milford
This new construction upscale beach house in Milford is located six houses from the beach, offering proximity to Silver Sands State Park and convenient access to Yale and New Haven dining.
This 2600 sq ft beach house features 3 bedrooms, 2 bathrooms, and can accommodate up to 6 guests, boasting a chef's kitchen, a third-floor rec room with water views, in-unit laundry, a private office, and outdoor Trex decks.
Luxurious, Direct Waterfront Home With Private Beach - Stratford, CT
10 18 reviews
Stratford, CT
12/25 – 12/31
$1911/nighttotal: $11466 (6 )

Luxurious, Direct Waterfront Home With Private Beach

4 2
apartment , Milford
This beachfront Milford home offers direct access to Walnut Beach and Silver Sands, and is within three miles of Port Milford and The Coastal Center at Milford Point.
This 4,500-square-foot house features four bedrooms, four bathrooms, and accommodates up to ten guests, boasting a jacuzzi, fitness center, and a private balcony with free WiFi, plus a fully equipped kitchen and on-site amenities including barbecue grills and a playground.
Pet Friendly Milford Beachfront Home - Stratford, CT
Stratford, CT
06/27 – 06/29
$1603/nighttotal: $3206 (2 )

Pet Friendly Milford Beachfront Home

5 8
house , Milford
This beachfront home is located in Stratford, a short distance from Milford, with Walnut Beach a 10-minute walk away and Silver Sands State Park Beach 1.5 miles away. The home offers direct access to the beach, making it an ideal spot for enjoying the sand and surf. This spacious 5-bedroom vacation home features a fully equipped kitchen, a comfortable living area with a fireplace, and a large terrace with outdoor furniture. Guests can enjoy a range of amenities, including a tennis court, a garden, a barbecue area, and free bikes for exploring the surrounding area.
The B&w Haven 5br Home With Yard Theater + Office - Stratford, CT
8.8 9 reviews
Stratford, CT
08/12 – 08/26
$447/nighttotal: $6258 (14 )

The B&w Haven 5br Home With Yard Theater + Office

5 2
apartment , Bridgeport
This five-bedroom Brooklawn-St. Vincent home is conveniently located a short walk from Bridgeport's Downtown South Historic District and St. Vincent's Medical Center, and within a mile of Svihra and Lafayette Parks.
This 2,000-square-foot vacation rental sleeps up to 11 guests and boasts a fully equipped kitchen, free Wi-Fi, a balcony, and parking, making it ideal for families or groups visiting Bridgeport.

Our Favorite Family-Friendly Vacation Rentals in Stratford, CT

These family-friendly vacation rentals in Stratford, CT offer plenty of room to spread out near local beaches.

Tranquil Beach Haven On The Connecticut Coast! - Stratford, CT
9.7 46 reviews
Stratford, CT
08/12 – 08/26
$403/nighttotal: $5642 (14 )

Tranquil Beach Haven On The Connecticut Coast!

1 2
apartment , Milford
This charming Milford home is located just four houses from the sandy beach of Long Island Sound in a quiet residential neighborhood. The apartment has consistently earned excellent ratings from previous guests for its cleanliness, location, and overall experience.
The apartment offers 700 square feet of living space with two bedrooms, one bathroom, and a capacity for five guests. Enjoy a fully equipped kitchen, a spacious backyard with a barbecue grill, a Jacuzzi, and easy access to downtown Milford, Charles Island, and the beach.
Stunning Sunsets & Coastal Charm - Stratford, CT
Stratford, CT
08/12 – 08/26
$375/nighttotal: $5250 (14 )

Stunning Sunsets & Coastal Charm

1 2
house , Milford
This Milford vacation rental is situated a 2-minute walk from Fort Trumbull Beach and 1.2 miles from Silver Sands State Park, offering direct access to a private beach area.
This 1350 square foot beach house accommodates up to 7 guests, featuring 1 bedroom, 2 bathrooms, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, free private parking, a private garden, and a terrace with an outdoor dining area.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Stratford, CT
8.8 10 reviews
Stratford, CT
06/27 – 06/29
$1641/nighttotal: $3282 (2 )

Charming Colonial For Events! Perfect For Family Reunions And Group Getaways!

6 8
apartment , Bridgeport
This Bridgeport colonial home rental, located in the Downtown South Historic District near Perry House, offers easy access to Beardsley Zoo, The Discovery Museum's Adventure Park, and Fairchild Wheeler Golf Course.
This 3,300-square-foot residence boasts six bedrooms, four bathrooms, off-street parking for six cars, and an expansive lawn, comfortably accommodating up to twelve guests with amenities including a microwave, air conditioning, and updated stainless steel appliances.
Ct Walnut Beach Cottage Sup Heaven - Stratford, CT
9.5 61 reviews
Stratford, CT
08/12 – 08/26
$500/nighttotal: $7000 (14 )

Ct Walnut Beach Cottage Sup Heaven

1 2
apartment , Milford
Located on the waterfront of Milford, this charming cottage offers easy access to the beach, just a short walk away. It has received excellent ratings for its location, cleanliness, and amenities, making it a great choice for travelers.
The cottage has three bedrooms, two bathrooms, and can accommodate up to seven guests. It features a fully equipped kitchen, a private backyard with a grill and tiki torches, and access to bikes, a kayak, a stand-up paddleboard, and a beach cart. Guests can enjoy water sports, explore the surrounding area, or relax in the comfortable and inviting atmosphere of the cottage.

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Best Stratford, CT vacation rentals with parking

Walnut Beach Escape Fenced Oasis Yard - Stratford, CT
10 118 reviews
Stratford, CT
12/25 – 12/31
$517/nighttotal: $3102 (6 )

Walnut Beach Escape Fenced Oasis Yard

2 2
apartment , Milford
This charming Milford apartment is located in the vibrant Walnut Beach district, just steps from the beach, cafes, shops, and the Walnut Beach concert pavilion. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom, one-bathroom rental comfortably sleeps six guests. The apartment offers a fully equipped kitchen, a spacious living area, a private backyard oasis, and a variety of amenities, including kayaks, bikes, and a pet-friendly environment.
#1 Beautiful Milford Beach Right Across Street -  Charles Island/silver Sands Pk - Stratford, CT
9.8 31 reviews
Stratford, CT
10/16 – 10/18
$468/nighttotal: $936 (2 )

#1 Beautiful Milford Beach Right Across Street - Charles Island/silver Sands Pk

2 2
apartment , Milford
This Milford apartment is directly across the street from the beach, a short walk from Silver Sands State Park, and just a few minutes from downtown Milford and I-95. The apartment has received excellent reviews from previous guests.
This two-bedroom, one-bathroom rental can comfortably accommodate up to six guests. The apartment features a fully equipped kitchen, laundry facilities, a private backyard, a patio, and a secure keypad entry.
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min Walk - Stratford, CT
9.4 8 reviews
Stratford, CT
10/16 – 10/18
$206/nighttotal: $412 (2 )

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min Walk

1 2
apartment , Bridgeport
This pet-friendly apartment rental in Bridgeport's Downtown is a 5-minute walk from the Bridgeport Train Station, near Baldwin Plaza Shopping Center and the historic Bridgeport Downtown South district, offering easy access to Beardsley Zoo and the Discovery Museum.
The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen, free Wi-Fi, a smart TV, air conditioning, on-site parking, and proximity to the Bridgeport Bluefish Baseball Club.
#37 - Luxury Collection - Stratford, CT
8.4 5 reviews
Stratford, CT
12/25 – 12/31
$546/nighttotal: $3276 (6 )

#37 - Luxury Collection

2 2
apartment , Stratford
This modern farmhouse rental in Shelton, Connecticut, offers easy access to Stratford's Boothe Memorial Park and Museum, as well as nearby hiking trails along the Far Mill River.
This 980-square-foot, two-bedroom, two-bathroom home sleeps four and features a gourmet kitchen, private deck with grill and fire pit, high-speed Wi-Fi, and a master suite with a dedicated workspace and river views.

Browse Vacation Rentals with a Pool in Stratford, CT

Enhance your coastal getaway with a Stratford, CT vacation rental featuring a pool.

Connecticut’s Finest Estate - Stratford, CT
Stratford, CT
06/27 – 06/29
$3995/nighttotal: $7990 (2 )

Connecticut’s Finest Estate

1 8
apartment , Trumbull
This Trumbull, Connecticut, estate offers a private, secluded getaway with five bedrooms and five bathrooms, comfortably accommodating ten guests.
The 5-bedroom house boasts a gourmet kitchen, game room, wet bar, swimming pool, Jacuzzi, and ample outdoor space including a fire pit, perfect for entertaining.
Cozy Studio Unit - Stratford, CT
9.8 77 reviews
Stratford, CT
10/16 – 10/18
$186/nighttotal: $372 (2 )

Cozy Studio Unit

1 2
apartment , Trumbull
This studio apartment is conveniently located in Trumbull, just a short drive from major highways, the Trumbull Mall, and the seaside beach. It consistently receives excellent ratings for location, cleanliness, and overall experience. The apartment features a comfortable pull-out bed and has a guest capacity of 4. Amenities include a fully equipped kitchen, a private garden, a swimming pool, and on-site parking.
Amazing Waterfront Front Next To Lighthouse - Stratford, CT
9.8 28 reviews
Stratford, CT
12/25 – 12/31
$1778/nighttotal: $10668 (6 )

Amazing Waterfront Front Next To Lighthouse

6 2
apartment , Stratford
This Stratford apartment is located directly on Long Island Sound, just a short drive from the train station and a scenic two-hour train ride to New York City. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This spacious 6-bedroom, 5.5-bathroom home features 4800 square feet of living space. Amenities include a private pool, spa, and outdoor kitchen, as well as access to two beaches, a golf course, and a golf cart.
1st Flr Apt Your Private Resort, Now Family-ized: 1 Br + Lr Suitable For 2 Kids - Stratford, CT
9.4 403 reviews
Stratford, CT
12/25 – 12/31
$162/nighttotal: $972 (6 )

1st Flr Apt Your Private Resort, Now Family-ized: 1 Br + Lr Suitable For 2 Kids

1 2
apartment , Shelton
This Shelton apartment is a secluded retreat surrounded by woodlands, offering privacy and tranquility just 5 minutes from the Connecticut Sports Center and within a 15-minute drive of over 80 eateries. It has excellent user, location, and cleanliness ratings.
The apartment has one bathroom, a floor area of 620 square feet, and a guest capacity of four. It features a fully equipped kitchen, a home theater with a 66-inch HD Smart TV, and outdoor amenities including a swimming pool, hot tub, fire pit, and bocce court.

Discover Vacation Rentals by the Sea in Stratford, CT

Enjoy a relaxing beach getaway with these coastal and seaside vacation rentals in Stratford, CT. Book your next shoreside stay today.

Stylish Sheek Loft 
Ricport Studio 2, Downtown - Stratford, CT
9.8 146 reviews
Stratford, CT
08/12 – 08/26
$136/nighttotal: $1904 (14 )

Stylish Sheek Loft Ricport Studio 2, Downtown

1 2
apartment , Bridgeport
Beautiful 5-bedroom Home Close To The Water - Stratford, CT
Stratford, CT
06/27 – 06/29
$851/nighttotal: $1702 (2 )

Beautiful 5-bedroom Home Close To The Water

5 8
apartment , Milford
Walnut Beach Luxury House: Steps To Private Beach - Stratford, CT
10 4 reviews
Stratford, CT
12/25 – 12/31
$861/nighttotal: $5166 (6 )

Walnut Beach Luxury House: Steps To Private Beach

1 2
apartment , Milford
Welcome, Two Bedroom Apartment - Stratford, CT
8.4 17 reviews
Stratford, CT
06/26 – 06/28
$229/nighttotal: $458 (2 )

Welcome, Two Bedroom Apartment

2 4
apartment , Bridgeport

Top-Rated 5-Star Vacation Rentals in Stratford, CT

Indulge in a luxury vacation rental in Stratford, CT, where high-end design meets world-class 5-star comfort.

Beautiful, Cozy Basement Space - Stratford, CT
9.7 27 reviews
Stratford, CT
10/16 – 10/18
$135/nighttotal: $270 (2 )

Beautiful, Cozy Basement Space

1 2
apartment , Bridgeport

Best Vacation Rentals with a Steam Room in Stratford, CT

Relax in style with an on-site sauna at these premium Stratford, CT vacation rentals near the water.

Luxurious, Direct Waterfront Home W/ Private Beach - Stratford, CT
10 30 reviews
Stratford, CT
12/25 – 12/31
$1883/nighttotal: $11298 (6 )

Luxurious, Direct Waterfront Home W/ Private Beach

4 2
apartment , Milford
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