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

Holiday Homes in Southport

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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 holiday homes

A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

1. 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, (40 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is NZ$1,049
includes taxes & fees
21 Oct - 22 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

2. 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 NZ$472
includes taxes & fees
4 Oct - 5 Oct
Centric property close to all the great things in the city
A swimming pool at night with blue lighting.

3. 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 NZ$270
includes taxes & fees
4 Oct - 5 Oct
Business or Weekend escape
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

4. 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 NZ$1,041
includes taxes & fees
5 Oct - 6 Oct
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.

5. Elite room stay

Elite room stay
Bridgeport
The price is NZ$597
includes taxes & fees
3 Oct - 4 Oct
Elite room stay
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

6. 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.
The price is NZ$1,400
includes taxes & fees
5 Oct - 6 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

7. 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.
The price is NZ$1,613
includes taxes & fees
4 Oct - 5 Oct
4 Mi to Beach & Dtwn! Charming Fairfield Home
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

8. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is NZ$766
includes taxes & fees
5 Oct - 6 Oct
Gilded Age Luxury Surrounded by Nature
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

9. 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 NZ$1,274
includes taxes & fees
28 Oct - 29 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A bedroom with a bed, two bedside tables, a lamp, an air conditioning unit, a patterned rug, and a painting on the wall.

10. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
Renovated Beachside Retreat
A bedroom with two beds, a wooden dresser, and a mirror.

11. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is NZ$854
includes taxes & fees
7 Oct - 8 Oct
Cozy 1-bedroom house in welcoming Bridgeport
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

12. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NZ$2,761
includes taxes & fees
6 Oct - 7 Oct
Beechmont - Perfect for Family Retreat!
A two-story house with a porch, stone steps, and a variety of plants.

13. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
The price is NZ$2,235
includes taxes & fees
5 Oct - 6 Oct
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A modern kitchen with a marble island, bar stools, and a dining area with a table and chairs.

14. Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Milford
9.8 out of 10, Exceptional, (9 reviews)
"Very comfortable modern home, clean, great backyard, pet friendly Host was so accommodating and responsive, personal note at check-in "
United States
Traci F.
The price is NZ$801
includes taxes & fees
4 Oct - 5 Oct
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Room

15. #37 - Luxury Collection

#37 - Luxury Collection
Stratford
8.4 out of 10, Very good, (5 reviews)
"Peaceful spot, conveniently located."
United States
Katherine
The price is NZ$842
includes taxes & fees
8 Oct - 9 Oct
#37 - Luxury Collection
A modern kitchen with white cabinets, a marble island, and black bar stools.

16. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is NZ$1,578
includes taxes & fees
14 Oct - 15 Oct
Spacious Retreat with Game Room and Fire Pit
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

17. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (20 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is NZ$582
includes taxes & fees
6 Oct - 7 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

18. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is NZ$1,287
includes taxes & fees
7 Oct - 8 Oct
5BR Beach Home | Walk to Cove Beach + Private Yard
A campfire with a wooden table and benches by a lake.

19. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$555
includes taxes & fees
7 Oct - 8 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

20. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is NZ$1,636
includes taxes & fees
14 Oct - 15 Oct
5BR Beach House, Water Views, Steps to Beach, Backyard
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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"The room was very clean, staff was extremely friendly."
Angela 2-night trip
Posted 8 hours ago
Norwalk Inn & Conference Center

Find out more about Southport

Southport Holiday Homes information

Number of reviews
300
Accommodation
249 Holiday Homes
Lowest Price
NZ$270
Highest Price
NZ$2,761