Holiday Homes in Southport

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Southport

Business or Weekend escape
Pool

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$168
includes taxes & fees
8 Dec - 9 Dec
Business or Weekend escape
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (114)
"Peaceful, lovely neighborhood. Easy access to country drives. Quick drive to Stamford station. Helpful host. "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Beautiful historic home in Stony Brook!
Interior

Beautiful historic home in Stony Brook!

2.0 star property
9.2 out of 10, Wonderful, (5)
"This was our second stay at this charming cottage, perfect mix of colonial feel and modern amenities. Plenty of space for us and our dog. Everything we needed was included. Location is close to village and beach. "
Beautiful historic home in Stony Brook!
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Cozy Modern Home
Fridge, microwave, oven, stovetop

Cozy Modern Home

9.6 out of 10, Exceptional, (30)
"The house was clean, updated and well kept. We went on a guys hiking trip this house worked out perfectly for us. "
Cozy Modern Home
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Fridge, microwave, oven, stovetop

Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

10.0 out of 10, Exceptional, (34)
"Our stay at Gersende's property was delightful. We had seven friends together for a wedding and this house and property served as a much appreciated comfortable and peaceful retreat. The pool was lovely, the kitchen was well-stocked and functional and the homes quirks and charm grew on us a little more each day. We walked to GrayBarns Mercantile every morning for coffee and it was a quick drive from the grocery as well as the PJ Glass House. Gersende was kind, easy to reach and incredibly...
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Modern 2BR House w/ Fenced Yard & Wi-Fi
Fridge, microwave, oven, stovetop

Modern 2BR House w/ Fenced Yard & Wi-Fi

9.6 out of 10, Exceptional, (16)
"We had a blast staying at this property. The attention to detail in the amenities provided was amazing. We travelled with our infant and there was a high chair, pack & play, and baby bath available for us to use, this was perfect so we didn’t have to worry about traveling with these items. Loved the toiletry boxes provided for shampoo, conditioner, laundry pods, dish soap, & more! The location was perfect! Nice short walk to the delicious Walnut Beach Creamery, Walnut Beach Coffee House, and...
Modern 2BR House w/ Fenced Yard & Wi-Fi
Stylish Beach Home near Stamford Downtown/Beach
Property grounds

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (19)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
The price is AU$1,123
includes taxes & fees
1 Dec - 2 Dec
Stylish Beach Home near Stamford Downtown/Beach
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (5)
"The house was perfect for a family of 4 and a couple! It’s a fairly quiet neighborhood so it was a good place to come back to relax each day. Parking for 2 cars was helpful and the coded entry was very easy. Nice setup and thoughtful features. Angela was very responsive and friendly! Definitely recommend!"
The price is AU$823
includes taxes & fees
25 Nov - 26 Nov
McAngel Haven: 5 mins from Yale
Ocean Front Beach House with Private Beach Access - Newly Renovated!
On the beach, beach towels

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (12)
"We rented this house to celebrate my mother’s 80th birthday. The 6 of us had a great time. The house couldn’t be closer to the water. Beautiful house. Plenty of room for everyone. Get comfortable. Clean. Nice quiet street. Great host. Gave us games, towels, and there were more things in the garage that we didn’t even use. Weather wasn’t the best but we made the most of it. Water is very shallow for a long distance so you can easily walk out and hang around when the tide goes down. Overall...
Ocean Front Beach House with Private Beach Access - Newly Renovated!
The ARLO - Walk to Brewery and Restaurants
Dining tables

The ARLO - Walk to Brewery and Restaurants

10.0 out of 10, Exceptional, (1)
"Great proximity to restaurants graduation venue, Sacred Heart. We had a great time. The property is clean private, and really really cute."
The ARLO - Walk to Brewery and Restaurants
Family-Friendly, Near-NYC Norwalk Retreat
Fridge, microwave, oven, stovetop

Family-Friendly, Near-NYC Norwalk Retreat

2.0 star property
10.0 out of 10, Exceptional, (2)
"Met all of our expectations, made a very enjoyable stay with 2 little ones. Host was accommodating and went above and beyond to support our needs. "
The price is AU$883
includes taxes & fees
9 Dec - 10 Dec
Family-Friendly, Near-NYC Norwalk Retreat
Beautiful Hampton Long Island Family Getaway with Pool.
Interior

Beautiful Hampton Long Island Family Getaway with Pool.

7.6 out of 10, Good, (5)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is AU$2,521
includes taxes & fees
25 Nov - 26 Nov
Beautiful Hampton Long Island Family Getaway with Pool.
#37 - Luxury Collection
Private kitchen

#37 - Luxury Collection

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great Location, close to everything!! Place super clean and the bed was comfortable. New to CT, Fall colors amazing. Host was easy to work with, especially when we couldn't get coffee pot to work correctly. New Coffee pot but strange design. "
#37 - Luxury Collection
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (23)
"Washer downstairs unavailable, thermostat only on request, feather pillows (allergy). Otherwise it was ok with plenty of bedrooms and baths. "
Cheerful 4 bedrooms residential house.
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Fridge, microwave, oven, stovetop

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (60)
"We enjoyed our short stay at the cottage! The thoughtful amenities were appreciated (especially ALL your coffee needs except dairy, toiletries, filtered water ready in the fridge), and there were probably more we didn’t take advantage of…we were only there for 3 days and didn’t cook in the house but noticed the pantry was stocked with spices and cooking essentials. The beds and bedding were very comfortable. The outdoor area was lovely and well maintained but we didn’t use it much because of...
Adorable Cottage with Water Views, Across the street from Prime & other eateries
2 mini-bedrooms apartment with antique bathtub.
Interior

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.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
On the beach, sun-loungers, beach towels

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (115)
"Spectacular views from the second floor balcony! very clean and spacious! Highly recommend staying here. "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Outdoor pool, a heated pool

ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

10.0 out of 10, Exceptional, (23)
"The property is absolutely stunning, very peaceful and Zen! Olga is fantastic very caring and attentive to detail. This was the perfect anniversary getaway and I can’t wait to go back."
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Fridge, microwave, oven, stovetop

Private Renovated Home Convenient to Sacred Heart & Fairfield Universities

10.0 out of 10, Exceptional, (26)
"Jon is an excellent and very responsive host. His home is beautiful, very clean, well appointed, and organized. All the comforts of home are provided. This is our second time staying at this property and we will be back!"
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
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.
Don't see what you're looking for?
See all available properties in Southport
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Southport

Westport "Gold Coast" across from Southport beach
Property grounds

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (82)
"The property was perfectly located for my needs, nicely appointed, comfortable furnishings, spacious, nice light, and felt like home."
Westport "Gold Coast" across from Southport beach
Stamford Suites
Exterior

Stamford Suites

2.5 star property
6.8 out of 10, (766)
"All is well"
The price is AU$254
includes taxes & fees
30 Nov - 1 Dec
Stamford Suites
Business or Weekend escape
Pool

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$168
includes taxes & fees
8 Dec - 9 Dec
Business or Weekend escape
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals