Southport Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Vacation Rentals in Southport

Property grounds
Westport "Gold Coast" across from Southport beach

Westport "Gold Coast" across from Southport beach

Fairfield
10.0 out of 10, Exceptional, (96)
"Excellent stay and value. I hope to return. "
United States
Eric B.
Westport "Gold Coast" across from Southport beach
Lobby
Stamford Suites

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (78)
"It was great"
United States
Natalie
The price is ￥18,593
￥21,382 total
includes taxes & fees
Dec 28 - Dec 29
Stamford Suites
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
8.4 out of 10, Very Good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is ￥42,037
￥48,342 total
includes taxes & fees
Dec 11 - Dec 12
Guesthouse at Norwalk Inn
Lounge
Luxury Apartments by Hyatus at The Asher

Luxury Apartments by Hyatus at The Asher

4.5 star property
Downtown Stamford
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.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

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.
The price is ￥19,980
￥41,516 total
includes taxes & fees
Dec 11 - Dec 12
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Pool
Business or Weekend escape

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is ￥13,203
￥22,756 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Business or Weekend escape
Front of property
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5.0 star property
North End
The price is ￥131,447
￥205,530 total
includes taxes & fees
Dec 10 - Dec 11
Beechmont - Perfect for Family Retreat!
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
Kings Park
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.
The price is ￥18,873
￥27,775 total
includes taxes & fees
Dec 10 - Dec 11
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Exterior
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

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.
The price is ￥136,302
￥246,451 total
includes taxes & fees
Dec 10 - Dec 11
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Microwave, oven, stovetop, dishwasher
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

Norwalk
7.0 out of 10, Good, (2)
"This was a great house to stay in as we visited family whose house had a strict no dogs allowed in the house rule. The beds were comfortable and the house was clean and updated. We only stayed upstairs, we didn’t have a use for the in law apartment downstairs, but I loved that the backyard was fenced in and clean. We’ll be back again, maybe when the pool is open and the weather warmer and we would recommend the place for anyone looking for a clean, updated place to stay."
United States
Crystal S.
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
Dining
Peaceful Vintage Home with Private Pond in Redding, CT.

Peaceful Vintage Home with Private Pond in Redding, CT.

2.0 star property
Redding
9.4 out of 10, Exceptional, (3)
"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.
The price is ￥70,106
￥109,443 total
includes taxes & fees
Dec 19 - Dec 20
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,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

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.
The price is ￥18,640
￥30,569 total
includes taxes & fees
Dec 10 - Dec 11
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!

The Bella Vista St James! Waterfront house with a beach dock and so much more!

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.
The price is ￥207,459
￥321,496 total
includes taxes & fees
Dec 10 - Dec 11
The Bella Vista St James! Waterfront house with a beach dock and so much more!
Smart TV, fireplace, books
6 BR Mansion , Celebration Welcomes

6 BR Mansion , Celebration Welcomes

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

Centric property close to all the great things in the city

Brooklawn - St. Vincent
7.2 out of 10, Good, (13)
"This rental was great accommodation"
United States
Alma B.
The price is ￥24,464
￥46,192 total
includes taxes & fees
Dec 10 - Dec 11
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

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

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
The price is ￥13,203
￥25,435 total
includes taxes & fees
Dec 10 - Dec 11
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Pool
Stamford Grand Apartment + Cozy Den

Stamford Grand Apartment + Cozy Den

2.0 star property
Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Very nice stay."
United States
Anonymous traveler
Stamford Grand Apartment + Cozy Den
Interior
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

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

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

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 2 days ago
Hampton Inn by Hilton Shelton

Find out more about Southport

Search for holiday rentals in Southport on Expedia! You can easily find your home rentals, villas, holiday apartments in Southport using one of the methods below:

  • View our selection of featured holiday rentals in Southport
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Look no further and take a look at our great range of rental properties in Southport!

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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.