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

Southport Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Southport vacation rentals

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (115 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$219 nightly
The price is $252
Nov 18 - Nov 19
Total with taxes and fees
DUNE Fairfield Beach
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

2. 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
$252 nightly
The price is $274
Oct 20 - Oct 21
Total with taxes and fees
Spacious Studio with Pool Table
A modern living room with a large window, a sofa, a coffee table, and a TV.

3. 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
9.6 out of 10, Exceptional, (14 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
$174 nightly
The price is $197
Oct 25 - Oct 26
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

4. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.8 out of 10, Good, (6 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
$305 nightly
The price is $346
Oct 21 - Oct 22
Total with taxes and fees
Modern 2 Bed in BlackRock
A swimming pool at night with blue lighting.

5. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
$135 nightly
The price is $152
Oct 25 - Oct 26
Total with taxes and fees
Business or Weekend escape
A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

6. 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
$269 nightly
The price is $304
Oct 19 - Oct 20
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

7. 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, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
$504 nightly
The price is $571
Oct 21 - Oct 22
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

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

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
9.6 out of 10, Exceptional, (4 reviews)
"Nice place to stay "
United States
Maria Elena G.
$322 nightly
The price is $365
Nov 16 - Nov 17
Total with taxes and fees
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

9. Elite room stay

Elite room stay
Bridgeport
$302 nightly
The price is $342
Oct 19 - Oct 20
Total with taxes and fees
Elite room stay
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

10. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$327 nightly
The price is $376
Nov 5 - Nov 6
Total with taxes and fees
Guesthouse at Norwalk Inn
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

11. 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
6.8 out of 10, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
$205 nightly
The price is $233
Oct 19 - Oct 20
Total with taxes and fees
Centric property close to all the great things in the city
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

12. 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
9.4 out of 10, Exceptional, (19 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
$204 nightly
The price is $231
Oct 19 - Oct 20
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A neatly arranged bedroom with a bed, bedside table, bench, and wall decor.

13. 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
$264 nightly
The price is $299
Oct 19 - Oct 20
Total with taxes and fees
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
A room with a large arched window, a bed, a bedside table, a lamp, and a potted plant.

14. 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 Orange & Groovy Apt. was as described. All the amenities we needed and we had a lovely time and enjoyed the area. Will book again!"
United States
Betty W.
$204 nightly
The price is $231
Oct 20 - Oct 21
Total with taxes and fees
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

15. 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, (19 reviews)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
$559 nightly
The price is $634
Nov 18 - Nov 19
Total with taxes and fees
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A white room with a round table, two benches, and a window with a view of houses.

16. Stay at Black Rock Harbor

Stay at Black Rock Harbor
Black Rock Historic District
10.0 out of 10, Exceptional, (29 reviews)
"This house was perfect for our family. Will definitely use again when we're visiting family in the area."
United States
Laura L.
$779 nightly
The price is $884
Nov 1 - Nov 2
Total with taxes and fees
Stay at Black Rock Harbor
A modern living room with a sofa, coffee table, and a bed in the background.

17. Renovated 3BR Apt / Easy Check-In / FamilyFriendly

Renovated 3BR Apt / Easy Check-In / FamilyFriendly
West End - West Side
10.0 out of 10, Exceptional, (1 review)
"Unit was clean, beds were large and comfy. Very close to downtown. Would stay again!"
United States
Matthew
$307 nightly
The price is $348
Oct 19 - Oct 20
Total with taxes and fees
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
A beige sofa with blue cushions, a white vase with flowers, and a white door with a glass panel.

18. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
10.0 out of 10, Exceptional, (1 review)
"This was a great deal on the busy weekend we stayed. The space was even better than described."
United States
Derek H.
$261 nightly
The price is $297
Oct 20 - Oct 21
Total with taxes and fees
Modern Apartment with Private Entrance
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

19. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
$690 nightly
The price is $782
Oct 20 - Oct 21
Total with taxes and fees
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A cozy bedroom with a bed, a TV, a window with curtains, a ceiling fan, and string lights.

20. Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station

Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station
Downtown Bridgeport
6.0 out of 10, (3 reviews)
"Great experience. Very close to a lot of downtown restaurants and Bridgeton. 10 to 15 mnutes from the beach. Lots of added special touches and amenities. Great job by the host."
United States
David W.
$211 nightly
The price is $239
Oct 19 - Oct 20
Total with taxes and fees
Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station
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

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

8/10 Good
"Just wish we had a personal microwave in the room. The floors share a microwave and there was spilled food from someone who previously used it."
Ken 1-night trip
Posted less than an hour ago
The Armon Stamford Hotel & Conference

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 $79 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.

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?

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends: This vacation home rental outside of Southport is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Stepping Stones Museum for Children, 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.