Southport Vacation Rentals

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Vacation Rentals in Southport

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Stamford Suites

Aparthotel in Downtown Stamford

4.0 star property
6.2 out of 10, (78)
"It was great"
United States
Natalie
$120 nightly
The price is $138
Dec 21 - Dec 22
Total with taxes and fees
Stamford Suites
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

Apartment in Fairfield

3.0 star property
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$223 nightly
The price is $256
Dec 15 - Dec 16
Total with taxes and fees
DUNE Fairfield Beach
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Aparthotel in Norwalk

3.5 star property
8.4 out of 10, Very Good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$251 nightly
The price is $289
Dec 17 - Dec 18
Total with taxes and fees
Guesthouse at Norwalk Inn
Lounge
Luxury Apartments by Hyatus at The Asher

Aparthotel in Downtown Stamford

4.5 star property
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Vacation Home in Greenwich

9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
$213 nightly
The price is $241
Dec 10 - Dec 11
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Pool
Business or Weekend escape

Vacation Home in Stratford

9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
$130 nightly
The price is $147
Jan 1 - Jan 2, 2026
Total with taxes and fees
Business or Weekend escape
Front of property
Beechmont - Perfect for Family Retreat!

Vacation Home in North End

5.0 star property
$1,151 nightly
The price is $1,323
Dec 9 - Dec 10
Total with taxes and fees
Beechmont - Perfect for Family Retreat!
Exterior
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Vacation Home in North End

9.4 out of 10, Exceptional, (6)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
United States
April R.
$1,397 nightly
The price is $1,581
Dec 9 - Dec 10
Total with taxes and fees
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Apartment in Kings Park

2.0 star property
10.0 out of 10, Exceptional, (13)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
$157 nightly
The price is $179
Dec 10 - Dec 11
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
On the beach, sun loungers, beach towels
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Vacation Home in Milford

10.0 out of 10, Exceptional, (134)
"Wonderful stay in a nice quiet neighborhood "
United States
Jacob M.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Dining
Peaceful Vintage Home with Private Pond in Redding, CT.

Vacation Home in Redding

2.0 star property
10.0 out of 10, Exceptional, (2)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
$616 nightly
The price is $697
Dec 15 - Dec 16
Total with taxes and fees
Peaceful Vintage Home with Private Pond in Redding, CT.
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Vacation Home in Shelton

9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
$174 nightly
The price is $197
Dec 9 - Dec 10
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Exterior
The Bella Vista St James! Waterfront house with a beach dock and so much more!

Vacation Home in Saint James

10.0 out of 10, Exceptional, (1)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
$2,256 nightly
The price is $2,578
Dec 9 - Dec 10
Total with taxes and fees
The Bella Vista St James! Waterfront house with a beach dock and so much more!
Smart TV, fireplace, books
6 BR Mansion , Celebration Welcomes

Villa in Norwalk

10.0 out of 10, Exceptional, (3)
"Lots of space and very convenient "
United States
Michael J.
6 BR Mansion , Celebration Welcomes
Fridge, oven, stovetop, coffee/tea maker
Centric property close to all the great things in the city

Vacation Home in Brooklawn - St. Vincent

7.2 out of 10, Good, (13)
"This rental was great accommodation"
United States
Alma B.
$265 nightly
The price is $299
Dec 9 - Dec 10
Total with taxes and fees
Centric property close to all the great things in the city
1 bedroom, desk, iron/ironing board, free WiFi
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Apartment in Downtown Bridgeport

10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveler
$145 nightly
The price is $164
Dec 9 - Dec 10
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Pool
Stamford Grand Apartment + Cozy Den

Apartment in Downtown Stamford

2.0 star property
9.6 out of 10, Exceptional, (5)
"Very nice stay."
United States
Anonymous traveler
Stamford Grand Apartment + Cozy Den
Interior
Beach house in Milford, CT

Vacation Home in Milford

10.0 out of 10, Exceptional, (1)
"Beautiful Home right on the Long Island sound, we had such a great time. Beach was easily accessible, The Host’s were amazing and went above and beyond in accommodating us. Highly recommend!!!"
United States
Alex F.
Beach house in Milford, CT
Interior
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

Vacation Home in Stony Brook

6.0 out of 10, (2)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
United States
Kathleen
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
Marina
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Vacation Home in Halesite

9.8 out of 10, Exceptional, (71)
"Wonderful cozy cottage with all the amenities!Great water views from this totally relaxing home - Thoroughly enjoyed our stay!"
United States
Rose D.
Adorable Cottage with Water Views, Across the street from Prime & other eateries
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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Top Southport Hotel Reviews

Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton

10/10 Excellent
"Service was great. Clean room and breakfast was good. "
Michael 1-night trip
Posted 1 day ago
Hampton Inn by Hilton Shelton

Find out more about Southport

Everything you need to know about Southport vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southport vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southport vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southport. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southport in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $138 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southport rentals

At Expedia, we put the best Southport vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southport vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Southport?

Yes, we have vacation rentals near well known attractions in Southport, or you can select a more remote option if you'd like a relaxing place to stay. Our travelers say Southport has a good selection of restaurants. Make sure you have time to check out the hockey games and beaches during your trip.

What are some of the best vacation home rentals that Southport has to offer?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: This vacation home rental outside of Southport is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Southport?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Southport stay.

What can I see and do in Southport?

Explore the area and family-friendly sights such as Norwalk Maritime Aquarium, or get out into nature at a spot like Southport Beach. In the larger area, you’ll find Fairfield Theater Company and Fairfield Beach.

What are vacation rentals like in Southport?

Vacation rentals are private accommodations you can reserve for a short or long stay in Southport. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for small groups.