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

Southport Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is AED 652
AED 974 total
includes taxes & fees
7 Oct - 8 Oct
DUNE Fairfield Beach
A modern living room with a flat-screen TV mounted on the wall, a round coffee table, and a sofa.

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
Spacious Studio with Pool Table
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.

3. 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, (18 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
The price is AED 514
AED 834 total
includes taxes & fees
30 Sep - 1 Oct
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

4. 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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AED 711
AED 1,933 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

5. Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveler
Luxury Designer 2 bedroom+office/3bed vacation home.
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

6. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 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.
Modern 2 Bed in BlackRock
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

7. 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 AED 1,055
AED 1,213 total
includes taxes & fees
8 Oct - 9 Oct
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

8. 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.
The price is AED 770
AED 2,005 total
includes taxes & fees
30 Sep - 1 Oct
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

9. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
A modern living room with a sofa, coffee table, and a bed in the background.

10. 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
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
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
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is AED 579
AED 950 total
includes taxes & fees
4 Oct - 5 Oct
Centric property close to all the great things in the city
A modern living room with a large window, a sofa, a coffee table, and a TV.

12. 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, (13 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is AED 408
AED 711 total
includes taxes & fees
30 Sep - 1 Oct
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

13. Elite room stay

Elite room stay
Bridgeport
The price is AED 760
AED 1,201 total
includes taxes & fees
30 Sep - 1 Oct
Elite room stay
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.
The price is AED 514
AED 834 total
includes taxes & fees
5 Oct - 6 Oct
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
A swimming pool at night with blue lighting.

15. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is AED 331
AED 559 total
includes taxes & fees
4 Oct - 5 Oct
Business or Weekend escape
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

16. 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 AED 2,237
AED 3,399 total
includes taxes & fees
30 Sep - 1 Oct
4 Mi to Beach & Dtwn! Charming Fairfield Home
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

17. 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.
The price is AED 784
AED 1,582 total
includes taxes & fees
6 Oct - 7 Oct
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

18. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
4 Mi to Beach & Dtwn! Charming Fairfield Home
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

19. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
The price is AED 1,054
AED 2,407 total
includes taxes & fees
28 Oct - 29 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
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 Stamford Hotel

The Stamford Hotel

8/10 Good
"Upon first glance, the hotel is good. Rooms are quiet, beds are comfortable, bathrooms are good. Peeling wallpaper , in the room and in the hallway in places, means things are dated. I would stay again, but it’s pricy for what you get."
Kimberly 1-night trip
Posted 8 hours ago
The Stamford Hotel

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.