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Compare 265 Vacation Homes in Southport with updated reviews, rates, and availability.

Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is SAR 281
SAR 507 total
includes taxes & fees
1 Oct - 2 Oct
Business or Weekend escape
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Front of the House, porch looking out on Long Island Sound
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (111)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
our inviting living room awaits, bathed in soft light and adorned with touches of homey charm
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
9.6 out of 10, Exceptional, (14)
"We loved our little cottage, it was a perfect size for us. The backyard was a great space for our grandkids to run around in, which was fun for them as well. It was close to family so we could easily have them over for the day. The owners were very kid an responded quickly to our questions also. We also met some of the neighbors who were a lot of fun too!"
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
Cozy Ocean Front Retreat with Private Beach!
Room
Cozy Ocean Front Retreat with Private Beach!
10.0 out of 10, Exceptional, (10)
"We enjoyed our stay very much; a nice open floor plan and nice big kitchen area, comfortable couches and chairs. A gorgeous prospect out the Master bedroom. "
Cozy Ocean Front Retreat with Private Beach!
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Exterior
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (111)
"Property was perfect for our family. Gym, steam shower, and theatre room were all amazing. Effortless check in/check out process. Gorgeous home and neighborhood. Communication with our host Chris was easy and fast. Thank you for everything:) "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
SUNSET OF MARSH & OCEAN
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (21)
"The house was in a great location, was well-stocked and clean, and the host was very responsive. Would definitely stay here again and highly recommend. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Property grounds
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (45)
"This house is beautiful and has everything you need, including a gorgeous view of the Sound. All communication was swift and easy. My family built some wonderful memories here this week!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
View of the front and outside of house with driveway and garage.
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
10.0 out of 10, Exceptional, (87)
"Excellent! Loved it! Home was more spacious than we ever thought. The rooms had so much character! Beautiful yard. Perfect setting. We would stay here again."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Lakeside luxury: beautiful, relaxing 4 bedroom home
Sit back and relax!
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, (13)
"This house was perfect for my group of 6 college friends. We hadn't gotten together in over 10 years and wanted to relax and catch up. The furniture and bedding were extremely comfortable, the kitchen had everything we could possibly need and more! Very spacious home with off-street parking for 6 cars. We loved it here!!! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Historic Connecticut Home w/ Grill & Spacious Yard
Weston Vacation Rental | 3BR | 2.5BA | 2,800 Sq Ft | Stairs Required
Historic Connecticut Home w/ Grill & Spacious Yard
10.0 out of 10, Exceptional, (2)
"House is even cooler than the pictures give it credit for. Beautiful and funky. We really enjoyed our stay!!"
Historic Connecticut Home w/ Grill & Spacious Yard
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Interior
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (15)
"We stayed at this unit for one week while our son participated at a camp at Sacred Heart University. This unit is located close to Fiarfield beaches - we brought our bikes and started each day with a ride to the ocean and dip in the water. It is also walking distance to restaurants and shops. The unit has everything you need to cook and is absolutely spotless! A big bonus was bringing our furry child (golden retriever). The manager is responsive and helpful. Highly recommend this unit!"
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Cheerful 4 bedrooms residential house.
Exterior
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (20)
"My friends and I stayed in Bridgeport for a weekend of music, and we had a great experience here! The owners were responsive and the place was exactly what we needed"
Cheerful 4 bedrooms residential house.
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Adorable Cottage with Water Views, Across the street from Prime & other eateries
10.0 out of 10, Exceptional, (58)
"Great location, attentive host. Very cute cottage - with everythng we beed. Cute outside (covered) space to relax. "
Adorable Cottage with Water Views, Across the street from Prime & other eateries
2 mini-bedrooms apartment with antique bathtub.
Private kitchen
2 mini-bedrooms apartment with antique bathtub.
10.0 out of 10, Exceptional, (18)
"Conveniently located to small downtown area & train into NYC. "
2 mini-bedrooms apartment with antique bathtub.
Cozy Modern Home
Exterior
Cozy Modern Home
9.6 out of 10, Exceptional, (26)
"Very nice place, stay there for a couple of nights for a get together, plenty of room. Only problem was some of the cleaning supplies where locked away where we couldn’t access it so we had to bring a mop and other supplies."
Cozy Modern Home
Catch some Zzz at Black Rock Harbor
Enjoy banquet dining adjacent to the kitchen, while savoring the gentle breezes and soothing sounds emanating from the nearby Seabright Beach.
Catch some Zzz at Black Rock Harbor
10.0 out of 10, Exceptional, (11)
"Loved this modernized beach cottage. Walking distance to food and Bev as well as the beach. Quiet neighborhood. Perfect stay. "
Catch some Zzz at Black Rock Harbor
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Exterior
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
10.0 out of 10, Exceptional, (25)
"Jon’s home is absolutely stunning - the pictures don’t do it justice. We had a bunch of family coming to visit for my son’s baptism and this was the perfect home away from home - well equipped with everything you could need or want, with plenty of space, comfy beds and spacious bathrooms. Highly recommend!"
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Lordship Charmer has it all! Comfortable stay, accessible, family friendly!
Living area
Lordship Charmer has it all! Comfortable stay, accessible, family friendly!
9.0 out of 10, Wonderful, (2)
"Very nice place close to the beach and nice restaurant. The host was very nice and did a very good banana cake."
Lordship Charmer has it all! Comfortable stay, accessible, family friendly!
Beautiful 5 bedroom Darien house with pool
Pool
Beautiful 5 bedroom Darien house with pool
Beautiful 5 bedroom Darien house with pool
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Private kitchen
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
10.0 out of 10, Exceptional, (3)
"The house is very nice, with cleanliness showing everywhere. It has everything you may need, and is quite comfortable. The host was very nice and easy to work with. The location is about two blocks from the beach, with restaurants, ice cream, etc even closer. Definitely 5 stars, highly recommended."
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Southport

Westport "Gold Coast" across from Southport beach
Exterior
Westport "Gold Coast" across from Southport beach
10.0 out of 10, Exceptional, (79)
"Very cute spot in a great location. "
Westport "Gold Coast" across from Southport beach
Stamford Suites
Property amenity
Stamford Suites
2.5 star property
6.8 out of 10, (747)
"It was more than i expected. "
The price is SAR 571
SAR 640 total
includes taxes & fees
7 Oct - 8 Oct
Stamford Suites
DUNE Fairfield Beach
Room
DUNE Fairfield Beach
3.0 star property
8.8 out of 10, Excellent, (35)
"Enjoyed the stay in the modern suite, located a short walk to the beach. Recommend the hotel and touring in the Fairfield, CT area. "
DUNE Fairfield Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.