A Gothic-style church with a tall steeple, large arched windows, and a clock tower.

Southport Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Southport vacation rentals

Classic Suite | Iron/ironing board, WiFi (free), bed sheets

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (103 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is ￥29,973
￥44,435 total
includes taxes & fees
Aug 24 - Aug 25
DUNE Fairfield Beach
Interior

2. 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
9.4 out of 10, Exceptional, (10 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is ￥16,010
￥29,194 total
includes taxes & fees
Aug 24 - Aug 25
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
1 bedroom, desk, WiFi, bed sheets

3. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is ￥27,119
￥48,831 total
includes taxes & fees
Aug 24 - Aug 25
Spacious Studio with Pool Table
Coffee/tea maker, fridge, microwave, oven

4. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 reviews)
"Cozy get away"
United States
Anonymous traveler
The price is ￥26,902
￥60,466 total
includes taxes & fees
Aug 2 - Aug 3
Modern 2 Bed in BlackRock
Pool

5. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (58 reviews)
"I love the layout of this apt. Perfect for 2 to 3 people, it was clean and nothing out of place. The host was great and communicated well. I will be looking for this place again next year."
United States
Shamel
The price is ￥13,886
￥23,933 total
includes taxes & fees
Aug 5 - Aug 6
Business or Weekend escape
Fridge, microwave, stovetop, cookware/dishes/utensils

6. Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place. Beds where comfortable. Would most definitely come back there again. Quiet and safe atmosphere. Not far from the highway. Host was very nice."
United States
Lisa J.
The price is ￥22,055
￥48,603 total
includes taxes & fees
Aug 3 - Aug 4
Zen, Spacious & Comfy 2 bed, Lux beds
Smart TV

7. 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, (15 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is ￥25,731
￥43,886 total
includes taxes & fees
Aug 3 - Aug 4
Centric property close to all the great things in the city
1 bedroom, desk, iron/ironing board, WiFi (free)

8. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is ￥22,872
￥37,085 total
includes taxes & fees
Aug 2 - Aug 3
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Private kitchen

9. Elite room stay

Elite room stay
Bridgeport
The price is ￥33,818
￥55,718 total
includes taxes & fees
Jul 31 - Aug 1
Elite room stay
1 bedroom, desk, iron/ironing board, WiFi (free)

10. Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
The price is ￥22,872
￥37,085 total
includes taxes & fees
Aug 1 - Aug 2
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Beach nearby, sun loungers, beach towels

11. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (38 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is ￥51,315
￥114,046 total
includes taxes & fees
Aug 2 - Aug 3
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Coffee/tea maker, fridge, microwave, oven

12. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveler
The price is ￥29,465
￥63,291 total
includes taxes & fees
Aug 25 - Aug 26
Renovated 2BR Retreat / Modern Comforts Included
Standard Room, 1 King Bed, Main Building | Property entrance

13. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is ￥58,650
￥67,447 total
includes taxes & fees
Aug 2 - Aug 3
Guesthouse at Norwalk Inn
Coffee/tea maker, fridge, microwave, oven

14. Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"Nice place to stay "
United States
Maria Elena G.
The price is ￥48,521
￥89,290 total
includes taxes & fees
Aug 4 - Aug 5
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
House (4 Bedrooms) | Interior

15. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is ￥68,615
￥124,873 total
includes taxes & fees
Aug 2 - Aug 3
4 Mi to Beach & Dtwn! Charming Fairfield Home
Coffee/tea maker, fridge, microwave, oven

16. 5 minute walk to beach, walk to town & train

5 minute walk to beach, walk to town & train
Fairfield Beach
10.0 out of 10, Exceptional, (26 reviews)
"Host was great. Had a great stay. "
United States
jeff d.
The price is ￥68,133
￥158,078 total
includes taxes & fees
Aug 1 - Aug 2
5 minute walk to beach, walk to town & train
2 bedrooms, iron/ironing board, travel crib, WiFi

17. The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
9.0 out of 10, Wonderful, (2 reviews)
"It was clean "
United States
Burton
The price is ￥28,230
￥61,871 total
includes taxes & fees
Aug 3 - Aug 4
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
House | 4 bedrooms, high-speed internet

18. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is ￥119,922
￥180,746 total
includes taxes & fees
Aug 26 - Aug 27
Stareway to Heaven in Fairfield
Coffee/tea maker, fridge, microwave, oven

19. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (16 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is ￥59,630
￥126,058 total
includes taxes & fees
Aug 19 - Aug 20
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

20. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is ￥29,407
￥38,066 total
includes taxes & fees
Aug 5 - Aug 6
2-bedroom apartmet No cleaning Fee
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southport Hotel Reviews

Danfords Hotel and Marina

Danfords Hotel and Marina

10/10 Excellent
"Great stay! Right on the water which great dining options. Rooms were massive!"
Rachel 2-night trip
Posted 5 hours ago
Danfords Hotel and Marina

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!

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, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: 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 4 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 Country Club of Fairfield and Fairfield Theater Company.

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.