Southport Vacation Rentals

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Check prices for these dates

Tonight
Dec 8 - Dec 9
Tomorrow
Dec 9 - Dec 10
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Vacation Rentals in Southport

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
DUNE Fairfield Beach
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
The price is ￥13,203
￥25,435 total
includes taxes & fees
Dec 9 - Dec 10
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Exclusive Apartment | Private kitchen | Mini-fridge, microwave, oven, stovetop
The Mansion Hotel-style

Aparthotel in Norwalk

2.5 star property
8.6 out of 10, Excellent, (19)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is ￥19,689
￥22,643 total
includes taxes & fees
Dec 13 - Dec 14
The Mansion Hotel-style
Lobby
Stamford Suites

Aparthotel in Downtown Stamford

4.0 star property
6.2 out of 10, (78)
"It was great"
United States
Natalie
The price is ￥18,593
￥21,382 total
includes taxes & fees
Dec 21 - Dec 22
Stamford Suites
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
The price is ￥42,037
￥48,342 total
includes taxes & fees
Dec 11 - Dec 12
Guesthouse at Norwalk Inn
2 bedrooms, iron/ironing board, travel crib, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Apartment in West End - West Side

10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is ￥16,440
￥43,449 total
includes taxes & fees
Dec 10 - Dec 11
Renovated 2BR Retreat / Modern Comforts Included
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.
The price is ￥17,265
￥38,028 total
includes taxes & fees
Dec 9 - Dec 10
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Fridge, microwave, oven, stovetop
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Apartment in Fairfield

10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is ￥19,292
￥48,903 total
includes taxes & fees
Dec 9 - Dec 10
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Fridge, microwave, oven, stovetop
Renovated 2 bedroom entire apartment w/parking

Apartment in Ansonia

10.0 out of 10, Exceptional, (1)
"Good location and great landlords."
United States
Ricardo S.
Renovated 2 bedroom entire apartment w/parking
1 bedroom, WiFi, bed sheets
Newly renovated Private bedroom near Stony Brook University

Vacation Home in Stony Brook

2.0 star property
8.0 out of 10, Very Good, (2)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is ￥23,067
￥44,812 total
includes taxes & fees
Dec 9 - Dec 10
Newly renovated Private bedroom near Stony Brook University
Front of property
Beechmont - Perfect for Family Retreat!

Vacation Home in North End

5.0 star property
The price is ￥131,447
￥205,530 total
includes taxes & fees
Dec 9 - Dec 10
Beechmont - Perfect for Family Retreat!
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.
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
Property grounds
Luxury Designer 2 bedroom+office/3bed vacation home.

Apartment in Brooklawn - St. Vincent

9.4 out of 10, Exceptional, (22)
"Beautifully appointed luxury 2 nd floor accommodations in the city of Bridgeport. Guests could comfortably stay for multiple nights with the well equipped kitchen and dining room space. "
United States
Tessa P.
The price is ￥26,142
￥69,673 total
includes taxes & fees
Dec 9 - Dec 10
Luxury Designer 2 bedroom+office/3bed vacation home.
2 bedrooms, iron/ironing board, WiFi, bed sheets
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Vacation Home in Stony Brook

2.0 star property
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
The price is ￥35,648
￥82,610 total
includes taxes & fees
Dec 9 - Dec 10
Stylish 2BR House Near Stony Brook University and shopping, fully renovated
Fridge, microwave, oven, stovetop
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Apartment in West End - West Side

10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
The price is ￥20,970
￥55,026 total
includes taxes & fees
Dec 9 - Dec 10
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Fridge, microwave, oven, stovetop
Beach Apartment in Woodmont Milford

Apartment in Milford

2.0 star property
9.0 out of 10, Wonderful, (2)
"Had a great stay!"
United States
Garry G.
The price is ￥27,183
￥68,151 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Beach Apartment in Woodmont Milford
Fridge, microwave, oven, stovetop
McAngel Haven: 5 mins from Yale

Vacation Home in West Haven

9.6 out of 10, Exceptional, (17)
"The property was amazing and clean lots of room. Everyone in the family enjoyed the property. I definitely would stay here again if available when I was trying to visit CT again. "
United States
Shalonda M.
The price is ￥35,648
￥82,158 total
includes taxes & fees
Dec 9 - Dec 10
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

Apartment in Brooklawn - St. Vincent

8.0 out of 10, Very Good, (1)
"It was clean "
United States
Burton
The price is ￥16,440
￥44,691 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Vacation Home in Shelton

2.0 star property
The price is ￥14,413
￥60,972 total
includes taxes & fees
Dec 9 - Dec 10
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
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
The price is ￥13,203
￥22,756 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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.
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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
  • Use the map to find apartments and other holiday homes in the Southport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southport while they last

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.