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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Southport vacation rentals

A beach with a wooden fence and rocks, leading to the water.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (119 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is AED 634
AED 953 total
includes taxes & fees
14 Dec - 15 Dec
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
The price is AED 481
AED 891 total
includes taxes & fees
19 Nov - 20 Nov
Spacious Studio with Pool Table
A large, two-story building with a symmetrical facade, multiple windows, and a covered porch area.

3. 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
The price is AED 1,146
AED 1,317 total
includes taxes & fees
6 Dec - 7 Dec
Guesthouse at Norwalk Inn
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
8.0 out of 10, Very good, (7 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.
The price is AED 591
AED 1,248 total
includes taxes & fees
29 Nov - 30 Nov
Modern 2 Bed in BlackRock
A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

5. 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.
The price is AED 552
AED 1,219 total
includes taxes & fees
15 Nov - 16 Nov
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
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.

6. 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)
"A hidden gem! We have stayed here twice now when attending concerts at Hartford Healthcare Amphitheater. A beautifully appointed room within walking distance to the shows!"
United States
Kim F.
The price is AED 514
AED 815 total
includes taxes & fees
16 Nov - 17 Nov
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Modern dining furniture complementing the living space.

7. 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 AED 452
AED 1,103 total
includes taxes & fees
30 Nov - 1 Dec
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.

8. 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.
The price is AED 734
AED 2,008 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with stainless steel appliances, a wooden island, and pendant lighting.

9. 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, (5 reviews)
"Nice place to stay "
United States
Maria Elena G.
The price is AED 598
AED 1,371 total
includes taxes & fees
18 Nov - 19 Nov
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A swimming pool at night with blue lighting.

10. 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
The price is AED 331
AED 530 total
includes taxes & fees
16 Nov - 17 Nov
Business or Weekend escape
A wooden deck with a white sofa, overlooking a residential area with houses and a view of the sea.

11. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is AED 3,372
AED 4,824 total
includes taxes & fees
24 Nov - 25 Nov
Stareway to Heaven in Fairfield
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (29 reviews)
"Great location and clean property. Some items were broken or missing, but overall, a nice stay."
United States
Cherie
The price is AED 525
AED 1,455 total
includes taxes & fees
15 Nov - 16 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

13. 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.
The price is AED 579
AED 939 total
includes taxes & fees
18 Nov - 19 Nov
Centric property close to all the great things in the city
A dining area with a wooden table and chairs, a white bench, and a window with a view of a brick building.

14. 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)
"Beautiful home, clean and exactly as described.We loved our stay and plan on returning.The host was wonderful to work with.An overall excellent experience."
United States
Tara C.
The price is AED 1,032
AED 2,391 total
includes taxes & fees
30 Nov - 1 Dec
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

15. Elite room stay

Elite room stay
Bridgeport
The price is AED 760
AED 1,205 total
includes taxes & fees
14 Nov - 15 Nov
Elite room stay
A modern kitchen with white cabinets, a stainless steel oven, a microwave, and a toaster.

16. 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 AED 433
AED 1,082 total
includes taxes & fees
30 Nov - 1 Dec
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Ideal for meals and memorable gatherings.

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

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.6 out of 10, Exceptional, (22 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.
The price is AED 1,387
AED 2,827 total
includes taxes & fees
7 Dec - 8 Dec
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A bedroom with a large window, a bed, a nightstand, a lamp, and a potted plant.

18. 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, (9 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 815 total
includes taxes & fees
16 Nov - 17 Nov
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
A living room with a beige sofa, a glass coffee table, and a ceiling fan.

19. 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
The price is AED 508
AED 1,264 total
includes taxes & fees
30 Nov - 1 Dec
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
A backyard with a swimming pool, wooden deck, lounge chairs, and string lights.

20. 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
Cranbury
8.8 out of 10, Excellent, (8 reviews)
"Great spot for our family. "
United States
Kevin I.
The price is AED 1,084
AED 2,150 total
includes taxes & fees
19 Nov - 20 Nov
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
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

La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent
"Jking"
Jesus 1-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham Stamford / New York City

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.